CHAPTER 4

NEWJACK

Sing Sing was a world of adrenaline and aggression to us new officers. It was an experience of living with fear—fear of inmates, as individuals and as a mob, and fear of our own capacity to fuck up. We were sandwiched between two groups: Make a mistake around the white-shirts and you would get in trouble; make a mistake around the inmates and you might get hurt.

At the Academy, prison had been likened to a village—a self-contained world with its own school, workshops, hospital, and so forth. But what they didn’t say was that prison was also a microcosm of a totalitarian society, a nearly pure example of the police state. The military provided the model for the chain of command; enlisted men and women were marshaled daily by their superior officers into a battle of wills with the mass of angry and resentful prisoners. We who were in uniform controlled nearly every aspect of their lives. And prison, more than any place I’d ever been, was about rules.

The Academy had taught us about rules the way a fundamentalist teaches the Bible in church, taking literally the injunctions about moneylenders and Armageddon and wives who existed to serve husbands. And then the congregation went out into the world, where most Christians were flexible about such strictures but still considered themselves devout, and justifiably so. A good cop, after all, wasn’t the one who ticketed you for doing thirty-three miles an hour in a thirty-mile-an-hour zone. A good cop enforced selectively, using his judgment.

I was intrigued by a Latino officer I’d seen in the lineup room. He was posted to a gallery in A-block. Like the rest of us, he kept his little yellow Standards of Inmate Behavior, All Institutions booklet in his breast pocket, but unlike us, he had written FUCK NO in block letters along the top edge of the booklet—the part that peeked out of the pocket. It was his personal message to inmates and, actually, a pretty good summary of the booklet itself. It made me think he was probably a good officer, funny but tough, an enforcer of the rules. Later, a classmate who would spend a week working with that officer told me how every morning an inmate would fix him his coffee, passing the mug out through the bars of his cell. That made me reconsider. There was no rule against it, but what favors was the officer passing back in the inmate’s direction? How could you ever trust an inmate enough to drink his coffee?

This fuzziness surrounding the rules was a strange counterpoint to the solidity of Sing Sing’s walls, the seeming immutability of the prison. During that long summer, from mid-May to late September, I thought about it as I walked the tunnels and corridors from the lineup room to various buildings up the hill. My classmates and I had been placed in the resource pool and worked all over the prison. Eyes cast downward toward the floor, I’d watch the yellow traffic lines painted down the middle of most hallways to keep opposing traffic on its proper side. There were broad perpendicular lines at gates, where inmates were supposed to stop and wait for permission to proceed. Of course, they hardly ever did. Had they ever? The lines struck me as wistful suggestions of a stricter time, of rules now observed in the breach, a memory fading like the strict lessons of the Academy.

A-BLOCK

Many times during those first months I was assigned to A-block. The mammoth cellblock required more officers to run it than any other building—around thirty-five during the day shift—but the senior officers there seemed particularly unfriendly to new officers, offering little encouragement and lots of criticism. The best way to fend off their comments, I decided, would be to try and enforce the rules as strictly as I could.

But, assigned to one of the vast eighty-eight-cell galleries for the first time, I found it hard to know where to begin. With the sheets hanging from the bars like curtains? The clothes drying on the handrails? The music blaring from several cells? I decided to start with the annoyance closest at hand: an inmate’s illegal radio antenna.

Inmates were allowed to have music. Each cell had two jacks in the wall for the headphones its occupant was issued upon arrival. Through one jack was transmitted a Spanish-language radio station; through the other, a rhythm-and-blues station, except during sporting events, when the games were transmitted instead. Inmates could have their own radios, too, but the big steel cellblock made reception very difficult. Telescoping antennas were forbidden, because they might be turned into “zip guns.” By inserting a bullet into the base of an extended antenna and then quickly compressing it, an inmate could fire the inaccurate but still potentially deadly gun. The approved wire dipole antennas were supposed to be placed within a two-by-four-foot area on the wall—where, apparently, they did no good at all.

To improve their chances of tuning in to a good station, inmates draped wires over their bars and across the gallery floor. Some even tied objects to the end of a bare strand of copper wire and flung it toward the outside wall, hoping that it would snag on a window and that they would win the reception jackpot. (When you looked up from the flats on a sunny day, you could sometimes see ten or twenty thin wires spanning the space between the gallery and the exterior wall, like the glimmering work of giant spiders.)

Antennas strewn across the gallery floor could cause someone to trip, and if they seemed likely to do so, I’d have the inmates pull them in. But the inmate in question on my first day as a regular officer in A-block—a short, white-haired man in his sixties—had gotten his off the floor by threading wire through a cardboard tube, the kind you find inside wrapping paper. One end of the tube was wedged between his bars at stomach level, and the other protruded halfway into the narrow gallery space between cell bars and fence, like a miniature bazooka.

“You’re gonna have to take this down,” I advised him the first time I brushed against it.

“Why’s that?”

“Because it’s in my space.”

“But I can’t hear if it’s in my cell.”

“Sorry. Try stringing it up higher on your bars.”

“Sorry? You ain’t sorry. Why say you sorry if you ain’t sorry? And where’d you get to be an authority on antennas? They teach you that in the Academy?”

“Look, you know the rule. No antenna at all outside the cell. I could just take it if I wanted. I’m not taking it. I’m just telling you to bring it in.”

“You didn’t tell that guy down there to bring his in, did you? The white guy?”

I looked in the direction he indicated. There were no other antennas in tubes, and I said so.

“You’re just picking on the black man, aren’t you? Well, have a good time at your Klan meeting tonight,” he spat out. “Have a pleasant afternoon. You’ve ruined mine.”

All this over an antenna. Or, rather, all brought into focus by an antenna. In prison, unlike in the outside world, power and authority were at stake in nearly every transaction.

The high stakes behind petty conflict became clear for me on the night during my first month when Colton and I were assigned to work M-Rec, one of the kinds of recreation that Sing Sing relied upon heavily in order to give the prisoners something to do. After dinner, instead of the gym or the yard, inmates could gather at the gray-metal picnic-style tables bolted to the floor along M-gallery, on the flats, to play cards or chess or dominoes, or watch the television sets mounted high on the walls.

“The rule is that they can’t be leaning against the bars of the cells,” the regular officer said to us, “and the cell gates are supposed to be closed.” You could tell from his “supposed” that this rule was not strictly enforced. Still, Colton, a lieutenant’s son, seemed strangely zealous. I think he couldn’t stand the laxity around us. As we walked along the dimly lit gallery, he challenged one inmate after another. I decided that to keep his respect, I had better do the same. At varying volumes, they objected. “What is this, newjack rec?” asked one older man in a kufi who was sitting right outside his own open cell. I gestured toward the door. He told me that he was always allowed to leave the cell door open during M-Rec. Well, not tonight, I said. He yelled and screamed. I closed the gate. He walked right up to me, stood less than a foot from my face, and, radiating fury, said, “You’re going to learn, CO, that some things they taught you in the Academy can get you killed.”

I would hear inmates utter these exact words several times more in the upcoming months at Sing Sing, a threat disguised as advice. (The phrasing had the advantage of ambiguity, and thus could steer the speaker clear of rule 102.10: “Inmates shall not, under any circumstances, make any threat.”) But I hadn’t heard those words spoken to me before, and that, in combination with the man’s standing so close, set my heart racing. I tried staring back at him as hard as he was staring at me, and didn’t move until he had stepped back first.

Some of the conflict we saw, of course, wasn’t only a fixed feature of prison life; it had roots in Sing Sing’s frequent changes of officers. New officers, as we’d already learned, irritated inmates in much the same way that substitute teachers irritate schoolchildren. To try to lessen these effects, the chart office would often “pencil in” a resource officer to the post of a senior officer who was sick or on vacation. That way, there wouldn’t be a different substitute every day.

One day in A-block, however, I was assigned to run the gallery temporarily assigned to one of my classmates, Michaels, whom I knew to be particularly lax. It was Michaels’s day off, which made me the substitute for a substitute. I knew before I even arrived that things would be chaotic.

My first problem came at count time, 11 A.M. Inmates generally began to return to their cells from programs and rec at around 10:40 or 10:45 A.M. The officers would encourage them to move promptly to their cells. By 11, anyone not in his cell and ready to be counted was technically guilty of delaying the count and could be issued a misbehavior report. Few galleries, therefore, had inmates at large after 11 A.M.

But on this day, Michaels’s gallery had a dozen still out. Michaels had grown up in Brooklyn and, more than most officers from the city, considered the inmates to be basically decent guys, his “homies.” He wanted them to like him. Once penciled in to this post, he had quickly learned all their names. I had helped him at count time once before, and when I complained about two inmates who were slow to lock in, Michaels replied that they were good guys. Though I had seen sergeants chew him out for looseness, he had told me privately that the sergeants could “suck my dick in Macy’s window” for all he cared.

I liked Michaels for acknowledging the inmates’ humanity. He had told me how much he hated A-block’s usual OIC, a big, pugnacious slob I’ll call Rufino, who told jokes such as “How do you know when an inmate is lying? When you see him open his mouth.” But I didn’t appreciate Michaels’s legacy of chaos that morning.

A group of three or four senior officers strolled by, to my relief—I was sure they’d been sent to help me usher in the stragglers. But they had no such plan. A couple of them glanced disapprovingly at their watches and then at me. They didn’t have to help, so they weren’t going to. Thanks, guys, I muttered to myself.

About an hour later, a couple of keeplocks returned from disciplinary hearings. The block’s keeplock officer, instead of borrowing my keys and ushering the inmates to their cells, called, “They’re back,” when he came through the gate and then disappeared. One of the keeplocks returned to his cell without trouble, but the second had other plans. It was Tuesday, he told me, and Michaels always let him take a shower on Tuesdays.

“Keeplock showers are Mondays, Wednesdays, and Fridays,” I said. “And Michaels isn’t here today.”

“C’mon, CO, don’t play tough. I’ll be out in a second.”

“No,” I said. He acted as though he hadn’t heard, grabbed a towel from his cell, and strode quickly down the gallery to the shower stall. I wasn’t overly concerned: I always kept the showers locked, just in case something like this came up, and felt confident that once I reminded him he would miss keeplock rec today if he didn’t go back, he’d turn around. Then I remembered. On this gallery, the lock mechanism was missing from the shower cell door. The shower was always open. Sing Sing. The inmate was a good foot taller than me and well muscled. I yelled through the bars into the shower that he’d lost his rec. He said, “Fuck rec.” I put the incident into the logbook, then wrote up a Misbehavior Report and had his copy waiting in the cell when he got back. He shrugged it off.

“I don’t give a fuck, CO,” he explained. “I got thirty years to life, right? And I got two years’ keeplock. Plus today, I got another three months. When they see this lame-ass ticket, they’re gonna tell you to shove it up your ass.”

The frustration was, he was probably right. Of all the inmates on a gallery, keeplocks were the hardest to deal with. There were no carrots left to tempt them with, and few sticks—especially for the long-termers. And now it was time for keeplock rec. I tried to match faces with cells as they headed out to the yard on that hot June day—it could help me when it came time to lock them back in. I was in the middle of letting them out when the keeplock officer reappeared. He gestured in the direction I was walking.

“Forty-three cell?” he said. “Hawkins? No rec today.”

“No rec for forty-three? Why’s that?”

“He doesn’t get it today,” he said, and disappeared.

I knew there could be several reasons for the inmate not receiving rec. He might have committed an infraction within the past twenty-four hours. Or he might have a deprivation order pending against him; in cases of outrageous misbehavior, a keeplock who was a “threat to security” could have his rec taken away for a day by a sergeant. Or—what I worried about in this situation—he might have pissed off the officer but not had a deprivation order pending. In that case, another officer was asking me to burn the keeplock’s rec as an act of solidarity. I hoped it wasn’t the last possibility and went on down the gallery, passing up forty-three cell.

The inmate called out to me shortly after I went by.

“Hey, CO! Aren’t you going to open my cell?” I ignored him until I was on my way back. He stood up from his bed as I approached.

“Open my cell, CO! I’m going outside.”

“Not today,” I said.

“What? Why not today?”

“No rec today.”

“Why not?”

“That’s what they told me.”

“Who told you that?”

I didn’t answer him, but I immediately felt I’d done something wrong. I returned to the office and tried to get the keeplock officer on the phone. I was going to insist on knowing his reason. What was up with this guy? The phone rang and rang. I called the office of the OIC and asked for him. He was outside now; couldn’t be reached, Rufino said. But Rufino was always unhelpful. I called the yard. He’d had to go somewhere, wasn’t there now. Shit, I thought.

Meanwhile, three keeplocks on their way out to the yard stopped separately to advise me that “forty-three cell needs to come out, CO.” I looked down the gallery. He was waving his arm madly through the bars, trying to get my attention. I walked down to talk to him.

“You’re not letting me out?”

I shook my head.

“Who said so?” He was angry now.

“I don’t know his name,” I lied.

“Well, what did he look like?” I declined to help out. “Then what’s your name? I’m writing up a grievance.” I told him my name. When I passed by the cell again an hour later, he had a page-long letter written out.

Instead of the classic newjack mistake of enforcing a rule that nobody really cared about, I had just enforced a rule that wasn’t a rule, for my “brother in gray.” I knew that many police admired that kind of thing. But it made me feel crummy. And with the grievance coming, I was going to have to answer for it.

I thought about how the senior officers hadn’t helped me during the count, how the keeplock officer hadn’t helped me when the two inmates came back, and how the same keeplock officer hadn’t explained to me the deal with forty-three, even when I asked. More than once at the Academy, I’d heard the abbreviation CYA—cover your ass. I knew how to do it, though I also knew there could be consequences. In the logbook, I made note of the time and wrote, “No rec for K/L Hawkins, per CO X”—the keeplock officer. And then I waited.

The chicken came home to roost about a month later. I knew it when I arrived at work and approached the time clock. Officer X, instead of ignoring me as usual, gave me a cold, hard stare. His partner, Officer Y, stopped me and asked if I was Conover. Yes, I said, and he gave me the same stare and walked away. It was because inmate Hawkins in cell 43 had slugged Officer Y the day before (as I’d since learned) that Officer X had wanted to send him a message that day.

A sergeant who was unaware of all of this approached me with a copy of the inmate’s grievance letter in the mess hall at lunchtime that same day. “Do you remember this incident?” he asked. I said yes. “You’ll just need to respond with a To/From,” he said, using department slang for a memo. “Do you remember why you didn’t let him out? Probably forgot, right?”

“Well, no, the keeplock officer told me not to.”

The sergeant wrinkled his brow. “Well, probably best just to say you forgot,” he said cheerily, and turned away.

“Sarge,” I said. “It’s in the logbook. I wrote in the logbook that he told me.”

“You’re kidding,” he said. “Why’d you do that?”

I shrugged. “I was new.”

“I’ll get back to you,” he said.

I wrote the memo the sergeant had asked for, told the truth, and felt conflicted. Days went by. Another sergeant called me in and told to me to see a lieutenant in the Administration Building. My memo was on the lieutenant’s desk, and he was poring over it. “So you say you logged this part about Officer X, right?” he asked. I nodded, expecting to receive a stern, quiet lecture on how not to fuck my fellow officer. But the lieutenant just nodded, cogitated a bit, and then picked up the phone.

I heard him greet a sergeant in A-block. “So Officer X remembers saying that to Conover now, is that right? And he’s going to write a new To/From? And you’ll take care of the deprivation order? Okay, fine.” And hung up.

He passed my memo to me over the desk. “Just write this up again, but leave out the name of Officer X,” he told me.

“And then we’re set?”

“All taken care of.”

I was relieved. Officer X was off the hook, which meant that maybe he wouldn’t hate me more than he already did. Apparently, a deprivation order would be backdated to cover his ass. And I had learned an important lesson: If you were going to survive in jail, the goody-goody stuff had to go. Any day in there, I might find myself in a situation where I’d need Officer X to watch my back, to pry a homicidal inmate off of me, at his peril. The logic of the gray wall of silence was instantly clear, as clear as the glare of hate that Officer X had sent my way when he heard what I’d done.

The single most interesting word, when it came to the bending and ignoring of rules, was contraband. To judge by the long list of what constituted contraband, its meaning was clear. In practice, however, contraband was anything but.

The first strange thing about contraband was that its most obvious forms—weapons, drugs, and alcohol—could all be found fairly readily inside prison. Some of the drugs probably slipped in through the Visit Room, but most, it seemed, were helped into prison by officers who were paid off. The Department had a special unit, the Inspector General’s Office, which followed up on snitches’ tips and tried to catch officers in the act; the union rep had even warned us about the “IG” at the Academy. A couple of times a year, I would come to find, a Sing Sing officer was hauled off in handcuffs by the state police.

But even in its lesser forms, contraband had many interesting subtleties. As officers, we were not allowed to bring through the front gate glass containers, chewing gum, pocket knives with blades longer than two inches, newspapers, magazines, beepers, cell phones, or, obviously, our own pistols or other weapons. A glass container, such as a bottle of juice, might be salvaged from the trash by an inmate and turned into shards for weapons. The chewing gum could be stuffed into a lock hole to jam the mechanism. The beepers, newspapers, and magazines were distractions—we weren’t supposed to be occupied with any of that while on the job. Nor could we make or receive phone calls, for the same reason. Apart from inmates smoking in their cells, smoking was generally forbidden indoors.

And yet plenty of officers smoked indoors. Many chewed gum. The trash cans of wall towers were stuffed with newspapers and magazines.

A much longer list of contraband items applied to inmates. As at Coxsackie, they couldn’t possess clothing in any of the colors reserved for officers: gray, black, blue, and orange. They couldn’t possess cash, cassette players with a record function, toiletries containing alcohol, sneakers worth more than fifty dollars, or more than fourteen newspapers. The list was very long—so long, in fact, that the authors of Standards of Inmate Behavior found it easier to define what was permitted than what wasn’t. Contraband was simply “any article that is not authorized by the Superintendent or [his] designee.”

You looked for contraband during pat-frisks of inmates and during random cell searches. One day in A-block, I found my first example: an electric heating element, maybe eight inches wide, such as you’d find on the surface of a kitchen range. Wires were connected to the ends of the coil, and a plug was connected to the wires. The inmate, I knew, could plug it into the outlet in his cell, place a pan on it, and do some home cooking. I supposed it was contraband because of the ease with which it could start a fire, trip the cell’s circuit breaker, burn the inmate, or burn someone the inmate didn’t like. And it must have been stolen from a stove somewhere inside the prison.

I was proud of my discovery and asked a senior officer on the gallery how to dispose of it and what infraction number to place on the Misbehavior Report.

“Where’d you find this?” he asked.

“Cell K-twelve, in a box behind the locker,” I said.

“K-twelve—yeah, he’s a cooker,” the officer said. “Cooks every night. Can’t stand mess-hall food. I don’t blame him.”

“Yeah? So what’s the rule number?”

The other officer said he didn’t know, so I made some phone calls, figured it out, and did the paperwork during lunch. While I was at it, an inmate porter stopped by and pleaded on behalf of the cooker. “He’s a good guy, CO. He needs it.” A few minutes later, to my amazement, a mess-hall officer called.

“You the guy who found that heating element?” he asked.

“Yeah. Why?”

“What are you going to do with it?”

“Turn it in.”

“Oh really?”

“Yeah. Why?”

There was a long pause. “Oh, nothing.” He hung up.

I finished my Misbehavior Report and stepped out of the office to let inmates back into their cells from chow. When I returned to the office, the coil, which I had placed on the desk, was gone.

“Where’d it go?” I asked the senior officer. “Did you move it?”

“What—oh, that heating thing?” he said offhandedly. “I gave it back to him.”

“Gave it back? Why’d you do that? I just wrote up a report.”

“Look, he’s a good guy. Never gives any trouble. I think he’s vegetarian. He really can’t eat that stuff they serve down there. Why don’t you go talk to him?” He made for the door.

I stared at him skeptically. He shrugged and was gone.

Unsure exactly why I did so, I went to talk to the inmate. He did seem like a nice guy, and thanked me profusely for not turning him in. Oh what the hell, I thought.

Not long afterward, I found another heating coil during a cell search in B-block. This time my sergeant, Murphy, saw it in my hands and insisted I turn it in. The paperwork that Murphy told me to fill out was even more elaborate than what I had imagined. Specifically, he said, I’d need to make an entry in the B-block cell-search logbook; to write a contraband receipt for the inmate, with copy stapled to a misbehavior report, to be signed by a supervisor in the Watch Commander’s Office, where I would submit all the paperwork and get the key to the contraband locker in the hospital basement, where I would also sign the logbook. Oh, and on the way to the Watch Commander’s Office, I should stop and pick up an evidence bag from the disciplinary office, in which to place the burner.

It was the end of my day. I knew that many officers, rather than plow through all this when their shift was over, would just drop the contraband in a trash can by the front gate and be done with it. Sergeant Murphy would never follow up. But some contrarian impulse drove me on. I finally made it to the Watch Commander’s Office and waited twenty minutes for my turn with the lieutenant. He looked at the heating element, then at my paperwork.

“Do you think this is a good use of the Adjustment Committee’s time?” he asked.

I shrugged and said I supposed it was. My sergeant must have thought so when he told me to write all this up, I added. The lieutenant blathered on about major versus minor offenses, the need to make judgments, and so on, apparently expecting me to say, “Oh, I get it!” and withdraw from his office. But it had been a lot of work. I had stayed late. I was pissed off about this and other things. I didn’t move.

“Okay,” the lieutenant finally said. “Leave it with me.” I stood to leave, wondering how to take this. The lieutenant hadn’t signed a thing. A CO at a desk near the lieutenant’s translated for me as I walked out. “If in doubt, throw it out!” he said with a big smile. And that was that.

No sooner would an officer become savvy as to which rules were commonly ignored, however, than somebody in a white shirt would appear to shake up his whole understanding of accepted practice. That person, for me and many other new officers, was Sergeant Wickersham. While everyone knows that prison can warp or distort the personalities of prisoners, few stop to consider how it can do the same to those who work inside. The most extreme example of this at Sing Sing was Wickersham, who seemed to be on duty every time I was assigned to A-block.

Wickersham, whose full head of silver hair, mustache, and chiseled good looks made him resemble a misplaced Marlboro man, was a rara avis even by Sing Sing standards. For one thing, he was the only white sergeant of the dozen or so there who wasn’t waiting to transfer somewhere else. Wickersham had seniority, but Sing Sing was home. Nor was he using his seniority to get a desk job, as were most of Sing Sing’s old-timer sergeants, the majority of whom were black. Sergeant Wickersham chose to work A-block, a high-stress post, because he wanted to, because he seemed to feel at home there.

Wickersham’s sworn mission, as any new officer knew, was to give new officers a hard time—to ride them, chew them out, dress them down. Most sergeants were more like support personnel, there to set you straight when you erred, but mostly to help when you needed a hand. Not Wickersham. His goal was to put the fear of God into new guys. But not in the manner of a drill sergeant. Wickersham wouldn’t raise his voice. He would not smile, would not move his eyebrows. His voice had little inflection, and he always seemed to speak through clenched teeth. This utter self-discipline reminded me of the actor Clint Eastwood playing an unsmiling renegade cop. But behind Eastwood’s super-machismo, redeeming it, was always a flicker of dark humor. No such humor appeared to reside in Wickersham. The word among new officers was: Watch out for this guy.

But watching out for Wickersham wasn’t easy, because he liked to operate with stealth. He had a public mode, and you’d see him early in the shift or at lunch, with a coffee mug in his hand (he’d clip it to his belt when finished) and a cigarette hanging from his mouth, talking to other sergeants or to a coterie of more senior officers he favored. But once the blocks got busy and officers were rushing from cell to phone to center gate, Wickersham would put down his coffee, pick up the radio, and head out on a solitary patrol, creeping up and down the empty south staircase, peeking around corners to catch us in slipups, blatant or imagined.

My first encounter with Wickersham took place on my first day as a regular officer. I was working on A-block’s J-gallery, one floor up from the flats. Someone had asked me to let a keeplock out of his cell, since he had an appointment outside the block. I was, of course, in the midst of doing ten other things, and the keeplock, when I walked down the gallery to get him, was in his boxer shorts and needed a few minutes to get ready. Five minutes later, when I returned to his cell, he still wasn’t ready. As I stood outside and waited, I could hear my phone ringing. Slowly, the keeplock emerged. But then, despite my urgings, he dragged his feet; he had things to discuss with the inmate in the cell next to his, and the one next to that. Official procedure was to escort a keeplock down a gallery by walking behind him, but with this guy that was going to take an hour. Meanwhile, my phone rang on. I knew I would see the inmate when he got to the center gate, so I hurried ahead to answer it.

Blocking my way suddenly was Sergeant Wickersham. He hadn’t been there a few seconds before. I nodded in recognition, but he didn’t nod back. “Why is that inmate out?” he asked in his Darth Vader voice. It looked painful for him to speak.

“Keeplock officer asked for him,” I said.

“Why,” continued Wickersham, drawing out the word sarcastically, “are you in front of him?”

He’d caught me cutting a corner. Months later, a seasoned officer would advise me, “Always have an answer in corrections. Always have an answer, and you’ll do just fine.” That day I had an answer of sorts—my phone was ringing, I was in a hurry—but I doubted it would fly with Wickersham. I had no problem with admitting mistakes, however, and thought the sergeant might be pleasantly surprised by candor.

“Guess I messed up,” I said. “Sorry. It won’t happen again.”

“Sorry?” he said. His expression soured ever so slightly, as though he’d just swallowed some grounds with his already-bitter cup of coffee. His anger turned into disgust. He’d wanted a fight and I’d just rolled over. Wickersham now looked at me as though I were beneath contempt. “Huh,” he said. And walked away.

Another time, I was taking the count on M-gallery when Wickersham again appeared out of nowhere.

“You afraid you’re gonna lose your keys?” he asked.

I had no idea what he was talking about. “What do you mean?”

“You’re walking with your hand against them,” he observed acidly. “Are you afraid somebody’s gonna take ’em?”

I looked down at the dozen or so keys hanging near my hip. Sometimes I felt like a horse with sleigh bells when I walked with those things, and when I had enough time to think about it, and didn’t want to advertise my approach to inmates who might be doing something illicit in their cells, I would put my hand against the keys to quiet them.

“What’s wrong with that?” I asked. This offense, I felt sure, was entirely of his own invention.

“Don’t do it.”

“Don’t? Why not?”

Wickersham walked away.

Another day, I was working upstairs with an older officer named Robinson. Thirty or forty keeplocks were due back from rec, and we had just heard an announcement to clear the galleries of all other inmates in anticipation of this return. As I was clearing O-gallery, a friendly inmate gave me a heads-up: Wickersham was lurking near the end gate. I finished and walked over to K-gallery to see how Robinson was doing. A few inmates were still out but, much more ominous, Wickersham was now at Robinson’s end gate, talking into his radio. I had an idea what was about to happen, and I was right. A few seconds later an announcement boomed over A-block’s PA system: “Officer on K-gallery, clear your gallery!” chided Rufino. “Keeplocks are on their way! Repeat, clear your gallery!” Wickersham, instead of speaking to Robinson directly, had radioed down to the Officer in Charge. Now everyone in the block knew there was some problem with the officer running K-gallery.

I started helping out the surprised Robinson, but then he caught a glimpse of Wickersham and figured out what had happened. Furious, he stormed down to the gate to confront the sergeant. With only some wire mesh between the two men, their shouting battle raged for five minutes. Robinson returned, sputtering, “I’m forty-four years old, and I will not be treated like a child. I hate that fucking asshole!” By mutual agreement, Robinson joined the ranks of officers embargoed from A-block because they couldn’t deal with the sergeant. I envied those officers, but I wasn’t the shouting-match type.

The humiliation tactic was one of Wickersham’s favorites, and I saw him use it again not long after the incident with Robinson. An OJT named Swiatowy was doing a pat-frisk. He had the inmate against the wall and properly told him to take everything out of his pockets and hand it over. During the transfer, the inmate’s comb fell to the floor. Sounding insolent, the inmate told Swiatowy that he’d better pick it up. Swiatowy was declining to do so when Wickersham stepped up.

“Do you have a problem with picking this inmate’s comb off the floor?” he asked. Swiatowy just stared at him. (“I think I’ve still got the scar tissue on my tongue,” he told me later.) Swiatowy said he would do it, but in the event, the inmate did. Wickersham may have had a procedural point to make, but humiliating the officer seemed to be a larger one.

“You can’t act afraid of him, though,” Miller counseled me one day in the lineup room. Miller was a recruit from my class who’d been spending a lot of time in A-block. He told me that it was all a test, that Wickersham would leave alone those officers who stood up to him. They’d earn his respect. On my next run-in, I decided, I’d try it.

I didn’t have to wait long. It was at the end of a difficult day—in B-block, actually—during which I’d had trouble getting some of my porters to follow orders. I was back on R-and-W gallery, which I had learned was known as a porter gallery, because so many of its inmates worked somewhere in the prison as porters. The problem with this situation for the gallery officer was that porters, in recognition of their labor (which, many days, amounted to little), were usually offered showers in the afternoon, after other inmates left the gallery for recreation. But some officers would give porters their showers early, and it was a constant struggle, if you were trying to follow the rules, to keep the shower-eager porters inside their cells and off the gallery until you had decided showers could begin.

The largest contingent consisted of gym porters, and because many were longtime inmates and there was power in numbers, they were especially demanding. On this day it was a gym porter who appeared outside the locked shower stall, wearing only a bathrobe and slippers, half an hour too soon.

“No showers till rec,” I told him. “You gotta wait in your cell.”

“I always get a shower now, CO.”

“Not today,” I said. “Return to your cell. No porter showers till rec.”

Mama Cradle had started “dropping the programs”—calling out inmate destinations, such as law library and commissary, waiting for the inmates to assemble near the front gate and then sending them out with an escort—so I was very busy pulling brakes. The inmate wouldn’t return to his cell. I ordered him in again. He was still there the next time I walked by, so I gave him a “direct order,” preliminary to issuing a Misbehavior Report, and a moment later, seeing that he was still out, I deadlocked his cell. This way, I figured, he’d be unable to leave the gallery, since he couldn’t reach his clothes, and I could deal with him when I had more time.

Then an inmate on my gallery got called on a visit, and he was entitled to a shower. I opened up a shower stall for him. My renegade porter lingered outside it. “You’d better not go in there when he’s done,” I warned him. But when I next saw him, that’s where he was, soaping himself. (Most shower stalls had no curtains.) I can’t wait to write this fucker up, I said to myself.

Finally, with recreation having been called, most inmates off the gallery, and things settled down, I went to find my disobedient porter and lock him into his cell. He was going to have to stay there today, missing rec, learning that actions had consequences. I was sure I’d find him standing outside it, still dripping from the shower, now feeling a little contrite. But he wasn’t there. I checked the other side of the gallery. Gone. Shit. He must have borrowed clothes and shoes from a friend and gone off to the yard with the others. But I knew who he was, and I could write him up anyway. The next officer could lock him in his cell.

By the time I finished writing up the Misbehavior Report, the sergeant for my shift had left. A less helpful sergeant was there in his place. He couldn’t sign my report, he said. I’d have to take it to the Watch Commander’s Office.

I sighed. The last time I’d been there was on my journey with the ill-fated heating element. After a long day on a difficult gallery, I wasn’t in the right frame of mind to go through that again.

But now here I was, back before the same lieutenant. Watching him read this time, I realized he was only semiliterate. I helped him as he stuttered through my report, trying hard to be patient, trying to take a little refuge in numbness. It was only two paragraphs. Finally, he got to the bottom.

“There’s too many loopholes in here,” he declared, twice. The infraction was so cut-and-dried, and my writing so plain and direct, that I was about to explode from frustration. “I don’t understand this,” he said finally, dropping the paper on his desk.

“What don’t you understand?” I asked, fighting the sarcasm that seemed my only defense against incompetence. Behind me, though I hadn’t seen him, Sergeant Wickersham had entered the room. Apparently, he signaled to the lieutenant.

“Get a clean form and meet me in the back room,” he said, as though doing me a favor. I got there first, and an officer sitting across the room counseled me to calm down. It had been a terrible day even before the shower incident, and now this. If they tell me when I get downstairs that I have to do overtime, I thought, I’ll quit.

Wickersham didn’t take the folding chair I set up next to mine. He sat in another chair, farther away. Speaking in such a low monotone (the faux-calm tone) that I could barely hear him, he asked what I had done before becoming a CO. “A million things,” I said.

“Answer specifically!” he thundered, glaring.

“Taxi driver, construction,” I began.

“Any military?”

“No.”

“You keep showing that attitude toward superiors and you’re going to have a lot of trouble around here, a lot of trouble,” he warned. “Just answer the question, just the facts.” Now he was the prosecutor.

He told me not to write a single thing on the new form, the implication being that I’d get it wrong. Then he read my report, and red-penned it. My “his cell” became “the cell.” “Who do you think it belongs to?” Wickersham demanded. “The inmate? Or the taxpayers who put out a hundred thousand dollars for each of these cells?” He asked me to tell him the whole story, and I actually had to think hard to remember it, because I had been so overwhelmed on the gallery. Upon hearing that I hadn’t called a sergeant and hadn’t locked the guy in the shower when I saw him there—I’d never even thought of it—Wickersham seethed. “This is an embarrassment!” he pronounced, waving my report in the air. “He’s laughing at you now, saying he fucked you! You thought you could avoid confronting him and then come running to Daddy!”

“Sarge, I’m not afraid of inmates. I burned rec for two of them today, and—” I began. I knew at some level that I had mishandled the situation, but Wickersham’s approach made admitting a mistake the last thing I could possibly do.

“An embarrassment! Humiliation!” he repeated several times. As he stood and turned, the CO at the table who had earlier told me to take it easy signaled me to relax.

“Can I ask a question?” I interrupted.

“What?”

“Even if I messed up—and now I see that I did—does that change the fact that he did what he did?”

The sergeant didn’t answer, just continued mumbling about my crimes and misdemeanors. “An embarrassment!”

Wickersham stood and, with great theatricality, threw all my paperwork into the trash. I tried to catch his eye as he glared at me, but he looked away. So much for earning his respect by standing up to him. Now my day had been an utter failure. Wickersham began walking around the room.

“Are we finished?” I asked.

“I’m finished,” he said. And left.

A crusty old instructor at the Academy with a flat-top crew cut and a mug of coffee seemingly grafted to his hand told us to learn from his mistakes: He had moonlighted as a local policeman in his off-hours from a prison upstate, and it had broken up his marriage.

“Enough cop is enough,” he said. “If you’ve got to work a second job, do anything besides police work. And my best advice is not to work a second job at all. Exercise, pursue a hobby, work on your car—anything to get the prison out of your system. Don’t take it home to the wife and kids.”

I was new enough to the job, that evening in June after the encounter with Wickersham, to still believe it was possible to leave prison behind me at night. After I got home, I went for a run, had a beer with dinner, then helped my two-and-a-half-year-old son get into his pajamas. I was doing well at keeping work off my mind until I noticed his younger sister with her hands on the slats of her crib, looking out. Unnervingly, it reminded me of the same view I had all day long. Like an inmate, she was dependent upon me for everything. These two jobs were too much the same, I thought with disgust. My son, tired but rambunctious, didn’t want to brush his teeth and, struggling, mistakenly hit me in the eye. I grabbed him angrily and shouted, made him cry. Well, there was one difference between him and the inmates, I thought darkly as I tried to calm us both down. He was destroyed when I got mad; they, on the other hand, seemed energized.

I thought I owed my wife, Margot, an explanation for my temper, but I didn’t know how to begin. Certainly, I didn’t want to fill her mind with all the unpleasant images from my day. She seemed stressed enough by her own job and the many other things she had to do, and so, avoiding the matter, we both just fell asleep.

I woke up suddenly in the middle of the night, having had a vivid dream. I’d been keeplocked. I’d startled a prison clerk in some grocery store-like setting, and that was the automatic punishment. Whether I was an officer or inmate was unclear, but it suddenly dawned on me, as I sat in my cell, that I’d missed the twenty-four-hour deadline for appealing the charges against me. As a result, I now faced a year of disciplinary confinement. The feeling of terror that seized me was so strong that it woke me up.

A month or two later, Margot and I took a brief vacation by ourselves in Jamaica. My officer friend Miller had, half facetiously, cautioned me against vacation, saying that in his experience, taking time off almost wasn’t worth the nausea of reentry. But as I packed my swimsuit, sunglasses, and Walkman, I knew it was the right decision. There was another life out there, a good life.

During my first three days in the tropics, slathered with sunscreen, gazing out over the ocean with a rum drink in my hand, I felt I’d successfully left Sing Sing behind. Then, on my fourth night, I dreamed vividly of Sergeant Wickersham. We were hunting together in the mountains somewhere, on horseback. He was still my superior, but in the dream he was tolerant toward me. Suddenly, he gestured at me to look to the left: Across a ridge, bathed in yellow light, was a tiger. Not an ordinary tiger, but one double the usual size. It looked tame, but I knew it might be very, very dangerous. Shhh, the sergeant said, don’t tell anyone there’s a tiger up here or all the hunters will come and shoot it. Everyone else thought there were no tigers left. He was letting me in on a CO’s secret.

The tiger had smelled or seen us, and I watched as it sniffed out our trail, came closer and closer behind us. I had the feeling that he was not following us but following me. Wickersham and I, on our horses, rode through a swinging glass door into a room, and soon it was just the tiger and us in there. A trick for you to try, Wickersham said: The tiger’s here because we’re carrying shrimp in our saddlebags. Chew some up and spray it out of your mouth at him. I did so, and the tiger hesitated, then fled—something to do with the seasoning, it seemed. Then the tiger came back and approached me on my horse. I repeated the trick, but this time only by going through the motions. I made him flee by just pretending I was going to spit! This was such a shock that again I woke up, trembling with happiness. Or was it fear?

I puzzled over that dream several times, and weeks later even wrote to a friend about it. “Seems to me it’s about domination, fear, predation,” Jay wrote back. “You’re caught between two tigers, Wickersham and the mass of inmates; you use an inmate technique—spraying—to defend yourself. The fact that it works is significant: It shows that for all his meanness, maybe you know you’re learning something valuable from Wickersham. But at the same time, he’s a dominating tiger to you.” The tiger coming indoors, Jay suggested, represented prison, a bottled-up wilderness within walls.

That sounded right to me, but while I was in Jamaica, it was much less clear. All I knew then was that even though my body was two thousand miles away, my mind was still trapped in Sing Sing.

Many officers were aggrieved by Wickersham, and I was delighted when one of my favorites, Goldman, from B-block, joined the club. Goldman was from Queens, a streetwise, muscled Air Force veteran in his forties, and I considered him a stalwart. One day I’d been pulling the brake on R-and-W when a high-spirited inmate running down the gallery (a rules violation) crashed into my back, almost knocking me over. It was apparently a mistake, though in the seconds after it occurred I wasn’t quite sure. During those seconds, Goldman appeared from the stairwell. As the inmate apologized to me, Goldman sized it all up and awaited my verdict: He was poised to jump the guy if I deemed it an attack. I hardly knew him, but I immediately loved him for that.

Goldman had been on the B-block door one day when a red-dot alarm was pulled inside. Per procedure, he exited the block and locked the gate from the outside. In a few minutes, Wickersham arrived with some red-dot officers from A-block.

“What did you see?” the sergeant demanded as Goldman unlocked the door.

Goldman told Wickersham where he thought the alarm had come from, which officers had been involved, and who had responded.

“You didn’t see anything,” replied the sergeant, dismissing him with a wave of his hand.

“Hey!” Goldman shouted as the sergeant moved past. “I’m an adult—you can treat me like an adult.”

Wickersham had turned and, according to Goldman, said, “It’s not my job to baby you.”

Offended, Goldman filed a grievance against the sergeant. He’d been treated disrespectfully too many times by him, he complained to some B-block officers a day or two later, and was too old to put up with it.

“Ah, ease up a little,” Chilmark, the officer in charge, counseled. “Nobody takes Wick seriously. He’s a fuckin’ bug.”

Bug was prison slang for nutcase. I’d never heard the expression applied to a member of the staff before, only to inmates. But it made sense, in light of the other information that circulated about the sergeant. What was known for certain was there for all to see: several circular round scars on his right forearm. He had been a POW in Vietnam, people said. Upon returning, he had started work as a Sing Sing CO and had been there just two and a half weeks when he and sixteen others were taken hostage and held by inmates for more than fifty hours during the B-block occupation of 1983. Those scars, everyone said, were cigarette burns inflicted by his captors during one of those experiences.

Hearing this story, I checked out some newspaper reports from the time. There was a bearded young Wickersham in a large photo after the incident was over, acting as spokesman for the just-released hostages. Instead of the dominating father figure abusing us for our own good, he was a chain-smoking newjack begging reporters to “bear with me—I’m a little nervous.” Being held hostage—suddenly finding yourself prisoner on a volatile inmaterun Death Row—could damage a person in fundamental ways. I thought about odd Sergeant Bloom. What was the legacy of those terror-filled days to Wickersham’s psyche?

Perhaps it was the particular context of the B-block riot that had marked Wickersham. In a report to the governor following the incident, a state watchdog gave credence to inmate and officer statements that the sergeant assigned to B-block the night the incident began had arrived at work drunk and had so angered inmates with his inappropriate and abusive orders that they gradually refused to comply with anything the officers said and finally rioted. The backdrop was a prisonwide feeling of rebelliousness: inmates in A-block had been demonstrating during the preceding weeks over prison mismanagement. But it seemed that the one sergeant had set it off.

At some level, I thought, Wickersham hated our innocence and wanted to cure it through abuse. But on another, by keeping new officers on their toes and keeping the blocks running according to the rules—by being a force for consistency—Wickersham may have been insuring himself against repeating the experience. The work inside was never finished. New officers always needed guidance, inmates always had to be listened to but at the same time kept in their place. Wickersham, I thought, probably derived a sense of purpose from obsessively riding herd on us. Part of it may even have been a generous impulse. But it came wrapped up in all sorts of nastiness.

In July, I was penciled in for two weeks as officer in charge of the A-block gym. This huge room was filled morning, afternoon, and evening with inmates, and my day shift spanned two of those times. It was regarded as a fairly good post in that you generally didn’t have to spend a lot of time telling people what to do. The regular officer, presently on vacation, had had it for years. Its main downside was risk. On a cold or rainy day, the gym could fill with upward of four hundred inmates, and there were moments when I would be the only officer there with them.

Depending on the time of day, eight to twelve porters were assigned to the gym. I had to put through their payroll, I was told, and therefore to keep porter attendance. (The twelve to fifteen cents an hour they earned was credited to their commissary accounts.) Because I knew the B-block porters to be a tight and surly bunch, I thought I’d better let the crew know right away who was in charge.

They arrived before rec was called, supposedly to get a jump on the cleaning. There was a lot to do, because an inspection of the block was scheduled for the next day. The gym had a full-size basketball court with a spectator area around it, a weights area the size of a half court, a table-and-benches zone for cards, chess, dominoes, and similar games, and two television areas. There was also a locked equipment room in front of which sat my desk, on an elevated platform, with a microphone on top. Instead of hopping to work, the porters turned on the TVs and sat down. I turned off the one most of them were watching.

“Gentlemen, I’m going to be here for the next two weeks and I want to talk with you about when the cleaning gets done and who does what.”

They sat silently.

“For example, who normally cleans today?”

At first, nobody said anything. There were stares of indifference and defiance. A pudgy inmate whose nickname, I would later learn, was Rerun finally spoke. “Don’t nobody normally clean today,” he said. “Tuesday’s the day off.”

“The day off. So when do you clean?”

“Mondays, Wednesdays, and Fridays. We know what to do.”

I tried wresting more details out of them, but they wouldn’t say more. Firing porters, I knew, was a bureaucratic procedure that took weeks; I’d be working elsewhere in the prison before the wheels had even begun to turn. And evidently the regular officer was satisfied with these men. Wishing I’d never started down this path, I finally had to settle for a plea dressed up as an order. “Those ledges up there? They’re covered with dust, and the inspectors will be looking. So tomorrow, make sure somebody takes care of that along with all the rest.”

“They don’t never check those ledges,” came the quick reply as I walked to my desk. And the TVs went back on.

The next day, somewhat to my surprise, six or seven of the porters set to work in earnest upon their arrival. For half an hour, they swept and mopped and picked up trash. As promised, they skipped the ledges. The place looked pretty good, and the inspectors never came.

I began to relax, and as I did, I began to understand the complex culture of the gym. There was, naturally, a big basketball scene—a league, in fact, with prison-paid inmate referees and a scoreboard and games that took place about every other day. The games were often exciting to watch—sometimes even a few officers would attend—but also nervous-making, as the crowds that gathered for matches between popular teams were partisan and players would sometimes get into fights.

Weight lifting was also popular, and when I was new at Sing Sing, it was intimidating to be faced with the huge, muscle-bound inmates who took it seriously. But soon I noticed that these purposeful, self-disciplined inmates were almost never the ones who gave us problems, and I came to agree with the opinion, generally held among officers, that the weights and machines were valuable. The only complaint I ever heard from officers was that inmates’ weight equipment was much better than what was provided to officers in the small weight room in the Administration Building.

Beyond these activities, the gym held many surprises. On a busy day, it seemed almost like a bazaar. A dozen fans of Days of Our Lives gathered religiously every day for the latest installment of their favorite soap. Behind them, regular games of Scrabble, chess, checkers, and bridge were conducted with great seriousness. (One of the bridge players, known as Drywall—a white-bearded man with dreadlocks—came from 5-Building; more than once when he was late, his partners asked me to call the officers over there and make sure he’d left so they could start their game.) At the table next to the games, an older man sold hand-painted greeting cards for all occasions to raise money for the Jaycees, one of Sing Sing’s “approved inmate organizations.” In a far corner behind the weight area, at the bottom of a small flight of stairs, a regular group of inmates practiced some kind of martial art. Martial arts were forbidden by the rules, but these guys were so pointedly low-key, and the rule seemed to me so ill conceived, that I didn’t break it up. In the men’s bathroom, inmates smoked—also against the rules but, from what I could tell, tacitly accepted.

A floor-to-ceiling net separated these areas from the basketball court. At court’s edge, a transvestite known as Miss Jackson would braid men’s hair as they watched the game or press their clothing with one of the electric irons inmates were allowed to use in the gym. She received packs of Newport cigarettes—the commissary’s most popular brand—as payment. Miss Jackson seemed a sweet man who was at pains to be noticed: She stretched the collar of her sweatshirt so that it exposed one shoulder, and cut scallop-shaped holes in the body so that it held some aesthetic interest. She often wore Walkman headphones, disconnected, just for the look. She must have been rich in cigarettes, and I wondered how she spent them.

Out on the court one day, just a few yards from Miss Jackson’s enterprise, four short-haired, long-sleeved, bow-tied members of the Nation of Islam stood in a close circle, sternly chastising another member of the group, who must have somehow strayed. One of them was also a gym porter, among those most courteous to me. The juxtaposition of such opposites—the ideologues of the Nation and the would-be sexpot—reminded me of street life in New York City.

I walked the floor every fifteen or twenty minutes, making sure no one was smoking too openly, telling those inmates who had put on do-rags to take them off (it violated the rule against wearing hats inside), and making announcements when there was room at the bank of inmate phones that were lined up on the flats near the front gate. (Inmates who had signed up on a list could be excused from the gym to make a call.) It wasn’t a bad job overall, and I suppose I should have been sad to see it go. But, as usual, I was simply relieved that nothing awful had happened under my watch.

I’d been away from A-block for a while—Sergeant Holmes had been sending me to B-block, which I liked better—but one day a different chart sergeant was on duty and back I went. I was sad to see that Rufino was still the officer in charge. For weeks, it seemed, he had sported a big shiner, courtesy of an inmate he’d angered, who one day had marched straight into Rufino’s tiny office and popped him in the eye. Couldn’t have happened to a nicer guy, I thought. Wickersham’s abusiveness seemed to enable Rufino’s; they were a twin star of meanness. Soon after he was punched, Rufino had spotted me chatting at the front gate with Allen while a keeplock I was escorting to the hospital waited to the side. Rufino called me into his office. “Don’t you ever turn your back on an inmate,” he scolded me fiercely.

Unfortunately, in practical terms, it was impossible not to turn away from an inmate occasionally—as Rufino’s shiner demonstrated. I didn’t point this out.

“Right, right, sure, sure,” I said.

The day of my arrival back on A-block, I told Rufino my post number and learned that I was an escort, which delighted me. I would be spending brief periods on a gallery but would also have a lot of time off, accompanying inmates to the mess hall and, later, to the commissary or package room or school building. I relaxed, knowing I wasn’t being put in charge of an unfamiliar gallery.

Before I could leave, though, Wickersham emerged from his office and looked over the day’s list of postings. L-and-P gallery, on the top floor, had been assigned to a brand-new officer. The guy was so new that he didn’t even seem worried about it. Wickersham scanned the group of us milling around the OIC’s office. “Switch him with Conover,” he told Rufino.

Son of a bitch! Did he have it in for me? I was sure he did, until someone later suggested he perhaps thought I was a competent gallery officer and that things were less likely to go wrong with me up there. I doubted that theory, and in any case, it was small comfort. I was going to be on L-and-P gallery all day.

There were a lot of keeplocks up there, which was never a good thing. P-north, in particular, had a high concentration: ten keep-locks, or one for every four cells. Several of these were in consecutive cells, which concentrated the bad vibe. Most of them left for keeplock rec about an hour into the shift. My problems began when they returned, an hour or so later. When the OIC announced the return over the PA system, my first job was to clear the galleries of other inmates. This was to minimize the chance of trouble—it was chaos enough to have a gallery full of keeplocks at large. The only inmates who were out on the galleries were three or four porters. Two of them were slow to return to their cells and lock in; when I saw the keeplocks arriving—and Wickersham lurking near the end gates—I ordered these two laggards into a shower stall on P-north, next to my office.

“Come on, CO, that’s bullshit!” one protested loudly.

“Yeah, CO, the regular never make us do that,” the other joined in. I got them in anyway, but the complaining caught on with the two or three keeplocks whose cells were on the other side of the shower.

“Let ’em stay out, CO!”

“You too harsh, man!”

“You want to start a slave revolt, CO? That’s what you doing?”

It was too early in the day for this, I said to myself. I walked over to the loudest keeplock, P-49, a somewhat scary-looking guy with unkempt dreadlocks, dirty clothes, and one gray and clouded eye.

“What I’m doing is absolutely appropriate, and you know it,” I said, trying to keep my voice low but unable to preserve my sangfroid. “Do me a favor. Shut up and let me do my job.”

“Woohoo, ‘Shut up!’ CO told me to shut up!” he crowed, completely jazzed, as I walked away. Others took up the hue and cry. “CO told him to shut up!” I walked back toward the center gate to start locking the returning keeplocks back into their cells.

And not a minute too soon. The keeplock officers, always eager to avoid extra work for themselves, were beating a hasty retreat down the center stairs.

“Hey!” I yelled after them as they waited for the officer downstairs to open the center gate. “How about sticking around a couple of minutes, help me get these keeplocks back in? I’ve got thirty of them out and don’t know where a single one locks. You going to leave me with that?” Grudgingly, they returned.

At 11 A.M., when it was time for the count, an officer newer than me appeared on the gallery. She was Reid, a tall redhead I had worked with one day when she was in training. The OIC had sent her to do the go-round—a list of where all the inmates planned to be after lunch, so that they could be tracked down in case they had a visit or had forgotten a medical appointment or the like. Go-round forms were filled out at the same time as count forms. To complete one, you stopped at each cell on a gallery and said, for example, “L-3, where are you going this afternoon?”

To let inmates know they’d better be dressed and decent, female officers always yelled, “Female on the gallery!” before setting out. That cry usually occasioned a dozen mirrors thrust out of cells so that inmates could get a good look at her. Sometimes catcalls would issue forth; today, they were especially obnoxious from P-north.

“Hey, Red! Show me that red pussy!” yelled one inmate. “You ain’t gettin’ enough, are you, Red?” called another. “I’m gonna give it you!” I had misgivings as Officer Reid marched bravely down P-north. She wasn’t the tough sort, just a farm girl who needed a job. And with her looks, she was an attention-getter. Some inmates tried to ejaculate on female officers; this had already happened to two of my classmates. I kept an eye on her until my phone rang.

Two minutes later, Reid was back in my office.

“You got a Misbehavior Form?” she asked, flustered.

“What happened?” I asked, handing her one.

“Masturbator,” she said.

“What cell?”

She told me. She seemed very tired.

“He’s a keeplock already—too bad,” I noted, checking my list. “Anything else?” Reid shook her head. I rang the sergeant’s office—Wickersham took the call—and let him know. He said to send her down.

I walked down P-north.

“What’s your fucking problem?” I demanded of the inmate. He was lying on his bunk, pants zipped up, smiling, looking smug. He wouldn’t answer. Upstate, I had heard, this kind of thing didn’t happen too often. Upstate, an inmate who spoke a wrong word to a female officer quickly regretted it.

“CO, you call the sergeant yet?” This was the voice of P-49, the keeplock I had told to shut up earlier in the morning. He’d been badgering me since then to get a sergeant upstairs to speak with him. I’d called the sergeant, a man who was working with Wickersham; he knew what P-49 wanted and said that he’d get back to him. I’d already told this to P-49. I repeated it to him again, impatiently, adding that there was nothing more I could do for him.

“Oh yes there is, CO. You can suck my dick!” P-49 proclaimed loudly. There were hoots of approval from the other keeplocks on P-north as I walked away.

P-49 continued to hector me the rest of the day. Unfortunately, his cell was close to my office. “CO, get away from my cell,” he’d yell when I walked by. “Homer, get back to the sticks.” His neighbor keeplocks would cheer in support; they were his chorus.

“He looks like a puppet, don’t he?” he taunted as I tried to keep my temper in check. I knew I had a loose-jointed style of running, but I had never heard it suggested about my walk before.

My nerves were frayed. I’d noticed that he was holding his mirror out on the gallery to keep track of my approaches and also that, against the rules, he sometimes left it balanced up on his bars. Once I had tried to grab the mirror, but he had anticipated that move and snatched it away before I could. Half an hour later, I noticed it was up again. Quietly this time, I walked up and took it. He was furious. “You better watch out when you come back by, CO,” he threatened, adding something that I couldn’t understand but that I presumed to be about shitting me down. That was an angry keeplock’s trump card.

In my eagerness to get the mirror, I’d placed myself on the wrong side of his cell. To get back to my office, I’d have to pass by again.

Another officer was on the gallery, escorting a civilian who was repairing the chain-link fence. “Cespedes, watch me as I go by P-forty-nine,” I said. Something told me that a witness might come in handy.

I collected myself and walked down the gallery as I normally would have. I probably should have sprinted past the cell, but I didn’t want to betray any fear. As I drew even with P-49, it all happened very fast: a gob of spit flew past my nose, with my cheek catching some spray, and then the keeplock’s arm swung out at full length, his fist catching my head just behind the ear. I stumbled forward and then looked back. Cespedes and the fence guy had both seen the incident. The fence guy’s mouth was wide open.

My heart was beating fast. I spent a minute calming myself down and then called the sergeant’s office. Wickersham answered. I told him what had happened.

“Who was it?”

“P-forty-nine. Folk.”

“Bring down your Misbehavior Report,” he said curtly. And hung up.

And leave the gallery without an officer? I wondered. That was against rules. But it was only a half hour or so until I was relieved, and it would take me a while to write the report.

Cespedes came into the office with another officer. He asked if I was okay (I only had a little bump) and what had led up to the incident. He turned over the mirror. On the back, in graffiti-style script, Folk had written: The Universal Don. Da Silva-Back Guerrilla. The Assassin. I told them about the harassment, told them Wickersham wanted to see me.

“Hey, Wick’s a good guy,” the other officer said. “He’ll take care of you.”

“Wickersham’s a horse’s ass,” I replied.

The man looked taken aback. Evidently, he was a Wickersham partisan. “Hey, pal, you’re on your own then,” he said, walking out.

Though he hadn’t said he was going to, Wickersham did send an officer to relieve me. She said things like, “Too bad we can’t go in there and show that asshole what the fuck is what.” I felt a little better.

When I arrived in his office downstairs, Wickersham glanced up and pointed to the chair beside his desk. I sat. He read my ticket and then went through a reprise of the just-the-facts interrogation he had administered that afternoon in the Watch Commander’s Office. This time I didn’t even care. He wrote out a new ticket for me in red pen. I watched his right arm as he did, with its six shiny, hairless, cigarette end—size circles. Other officers and a sergeant came in to offer sympathy and read the ticket, many of them assuming I had been shitted down. The nice thing about the finished ticket was that it all sounded worse than it was, containing words such as assault, unhygienic act, threats, etc. I did feel an element of shame in being a victim, and heard myself pointing out to everyone that this was the first time it had happened to me. Wickersham asked why I was walking close enough for him to reach me; I said that I hadn’t wanted to appear afraid, which he accepted, though he told me an officer should always walk as far as possible from the cells. “It might give you more time to grab his arm and break it,” he said, never cracking a smile.

It wasn’t really a joke to me, either. This very fantasy had already crossed my mind.

There was more paperwork. Wickersham had to send me to the ER to be checked for injuries. There, a nurse let me wash up with antibacterial soap. She was vociferous in her scorn for my assailant, and I felt warmly toward her, at least until she whispered, “I’ll bet he was black, right?” Wickersham entered with a Polaroid camera and took front and profile shots of me—required, I think, in case I made a claim for workmen’s comp. I looked at the photos as we walked to the Watch Commander’s Office. They were the first time I’d ever seen myself through Wickersham’s eyes, as it were. The officer in those shots appeared gaunt and wimpy to me.

The lieutenant who had been my shift commander asked if I was okay. Wickersham had already been in touch with the Box and had reserved a cell for my assailant. This may have spoken to his clout, since there often wasn’t room in there. I felt a touch of gratitude. He spoke to a team of officers, who were doing some overtime, about relocating Folk to the Box. “He might not go willingly,” he said, which was greeted with nods of satisfaction. I would have enjoyed watching the “relocation,” but they would never have let me. And to be honest, all I really wanted to do was leave.

As I walked through the front gate and outside, a sergeant whom I liked, Murray, called out. “Hey, Conover,” he said, and made a hawking sound. I smiled weakly.

“So you already heard, huh?” I asked.

“Heard about it in about a minute,” Murray answered. The prison was a small world. I wondered if the incident would make the announcements at lineup.

I had a pounding headache—it had been growing all afternoon—and as I pulled my car onto the highway, I experienced a vivid fantasy of A-block going up in flames, all the dross inside being consumed by the fire. And then came dissonant flashes of memory from that same day: the inmate who had tried to tell me a joke as I set up the locking board outside his cell; the inmate who had warned me about Wickersham approaching; the inmate whose classical guitar playing, particularly gorgeous in that setting, had drifted into my office around lunchtime. They weren’t all bad, I thought. Just most of them.

THE BOX

Officially, the dark, squat building was the Special Housing Unit, abbreviated SHU and pronounced shoe. But officers called it the Box. It was solitary confinement, a place of punishment within a place of punishment.

The Box had a doorbell and a heavy metal door with a peephole, and a barred gate as well. The structure was compact—redbrick, two-story. Each floor had two galleries, back to back, with fifteen cells. What made it fundamentally different from the other housing units of Sing Sing was that its inmates did not, as a rule, leave the building; in fact, they barely left their cells. Meals were delivered in the Styrofoam “clamshells” that restaurants use for takeout orders; library books, for those granted access to them, were wheeled in on a cart; inmate barbers were brought in to clip Box inmates one at a time at the end of the short galleries; even disciplinary hearings were conducted in the individual cells.

Half of the inmates in the Box, as it turned out—all thirty on the upper floor—were not disciplinary cases but men under protective custody, of which there were two kinds. Those who had asked to be protected were rats or rape or slicing victims who had identified their assailants—people who had enemies and, if left in the general population, might reasonably be expected to be hurt or killed. Among those in the Box involuntarily were victims who had not ratted out their assailants, and thus were feared to be either loaded guns, waiting for their chance to get revenge, or sitting ducks, soon to be victimized again. One inmate in there was a suspected gang member whose bed in A-block had been set on fire by a Molotov cocktail; another was a borderline bug convinced that a particular officer was trying to kill him.

Downstairs, by contrast, were the baddest of the bad—almost exclusively, inmates who had assaulted guards. It felt like a dungeon down there, in part because entry to the building was via the floor above, but also because it was darker, with smaller windows and lower ceilings.

The Box had the highest testosterone level in the prison, and somehow smelled like it—close, musty, with an acrid whiff of perspiration. Among COs, working in a max was considered more macho than working in a medium or anywhere else. To work in the Box of a max was—well, the maximum. The officers who chose it tended to be size large. They had a habit of tucking their trousers into the tops of their unlaced boots and rolling even their short-sleeved shirts up over their muscles, the casual SWAT team look.

One was a shaved-headed monster named Perlstein. The day I worked downstairs during OJT, he helped a fellow officer change his shirt; the man was so muscle-bound, he couldn’t reach back far enough to get his second hand into the sleeve hole. Perlstein then reviewed for us the pat-frisking procedure used on every single inmate before and after the inmate was released to the Box’s small exercise courtyard. “You, get on the wall,” he grunted at me.

“Now, if an inmate takes his hand off the wall—if he even looks back at you—you grab him like this,” he said, standing behind me and lifting one leg by the shin, “and push him ahead like this.” He squished me against the wall like a linebacker, my leg in hog-tied position. It hurt, and Perlstein knew it hurt.

He also reviewed the best places to strike with a baton: the exposed bones of the lower body. As I stood toward the wall, he ran his baton down the front of my shin.

“Ow.”

“Imagine if it was more than a little tap,” Perlstein said with satisfaction.

Perlstein gave me a lighter and sent me down to the north-facing gallery by myself, with instructions to light inmates’ cigarettes. (Like other inmates, they could smoke in their cells, but they were not allowed to have matches.) This was unexpectedly frightening. All I knew about Box inmates was that they were very, very bad. I thought of Agent Clarice Starling approaching Hannibal Lecter’s cell in The Silence of the Lambs. Downstairs at the Box was the lowest level of hell. The guy who had attacked Sergeant Bloom at Coxsackie had until recently resided here. David Berkowitz, the Son of Sam killer, was in the Box at Sullivan for nine years. The Box at Elmira held Lemuel Smith, who had picked up an unsupervised phone and tricked a young newjack, Donna Payant, into meeting him in a chaplain’s empty office at Green Haven Correctional Facility, where he raped and strangled her (and, according to Nigro, at the Academy, chewed off her nipples) in 1981—the last CO murdered on the job in New York State. He was insane, the devil incarnate, as bad as it got. But others here were no doubt almost as bad.

I assumed a confident pose as I passed through the gallery gate and slid it closed behind me. Unlike the Box at Coxsackie, which had seemed a true solitary confinement, with inmates hard-pressed to communicate with each other through solid-steel doors with Lexan windows, the cells here were barred. Some of the inmates had been leaning against their bars, talking; they stopped when I came into view. I held the lighter at arm’s length for two who had rolled their own, ready to spring back at any second. Both seemed to watch me closely. I tried not to meet their eyes. I pretended my face was made of granite.

Perlstein had a fair complexion; his pal, Proctor, was similarly proportioned, seemingly more human, and dark-haired. We ate lunch—our own, and sandwiches left over from the inmates’ feeding (this was against the rules)—near the exercise yard, and Proctor found it incomprehensible that I had once lived in Colorado. “And you left? I’d die to get out of here.” McDonough, as tall as the others but with a potbelly, was, like Perlstein and Proctor, in his late twenties or early thirties. I thought of him as the most arrogant of the crew. One day, in the corridor, when I was working a gate, he had snatched my radio off my belt to make some urgent call. Box officers always acted as though their business was urgent. But McDonough was also funny. One day, as we were leaving for home, he had called out to the chart sergeant at his desk, “Salaam aleikum!”—the phrase with which Black Muslims were always greeting each other solemnly.

A fourth officer, Gotham, showed me around another day when I worked the upper floor of the Box. Both floors had cages, or bubbles, in which one officer sat and operated the gates and cell doors by means of an ancient system of brass-handled levers that protruded from the wall. That officer wasn’t allowed to leave the bubble before a relief officer came in. (It made going to the bathroom difficult. A friend of mine explained that the downstairs officers sometimes solved the problem by resorting to a door that led from the bubble to the utility space between the cells—there was water in the floor area, and you could add to it.) Most other procedures had to be followed to the letter, many of them having to do with not opening more than one gate at a time, to ensure the strictest control over inmate movement.

Gotham was shorter than the other SHU guys and wore glasses, but he was quick to tell me that he wouldn’t hesitate to take down a recalcitrant inmate and that the inmates hated him; “In three years, I’ve had a hundred fifty use-of-forces,” he said. That was an average of about one per week. I wondered whether he was exaggerating or whether working the Box was just that tough. Gotham had been punched, too, he said. The year before, an inmate had broken a bone in his face and he’d needed six stitches.

Gotham maintained to me that if there was any trouble, pulling the radio’s emergency pin would be the wrong response, because “we take care of matters by ourselves here.” But he apparently forgot to tell the guys working downstairs. At just past 1 P.M. that day, there was a red-dot alarm called from the exercise yard. Three inmates were fighting; at least one had a weapon. The heavy front door was opened and I pulled wide the gate to the downstairs, standing to the side as some twenty-five to thirty officers responded. That was a lot of meat, and probably several times the number that would be required to subdue two or three inmates (which they promptly did). But emergencies in the Box got everyone’s attention.

The environment of the Box produced stunning acts of insanity and barbarism. During our OJT, Officer Luther had told us of a Box inmate nicknamed Mr. Slurpee, who would project a spray of urine and feces at officers—from his mouth. One day at lineup, a sergeant held up for display an interesting-looking noose about three feet long. “We think we take everything away that they could hurt themselves with,” he said. “And then we find this—made out of toilet paper.” He left it out for display after lineup. An inmate had rolled endless yards of toilet paper into tight cords before weaving the cords together into the noose. It was dingy from all the handling and, to judge by my tugging, seemed as tough as a real rope. Impressive, I thought. But, on another level: all this resourcefulness and the end result a noose?

One day, on my way out of the building at shift’s end, Chavez asked if I’d heard what had happened during the executive team’s inspection of the Box that day. No, I said, I hadn’t.

“The superintendent found a guy who hung himself up. He even cut him down.”

“The superintendent found him? Was the guy dead?”

“I don’t think so, not quite.”

The toilet-paper noose didn’t have anything to do with an officer’s laxity. Most SHU incidents did. One morning in August, a lieutenant told us during lineup that an SHU inmate had gotten out of the shower stall due to an improperly closed door, grabbed and broken a mop handle, and then smashed fifty-eight windows. (Because the building was old, the large windows were made of many small panes.) When he was finally overcome, a long glass shard with cloth wrapped around it for a handle was found in his waistband. I listened to this raptly, amazed by what it suggested about the man’s mental state. But the lieutenant had no interest in the inmate’s mental state. He was telling us about the incident in order to reemphasize the importance of strictly following procedures.

At the next day’s lineup, there was more: The day after the window-breaking incident, the officer working the downstairs bubble had had a container of urine chucked at him after a colleague failed to close the gallery gate. Then—this was starting to get embarrassing—a sergeant responding to the incident failed to secure a gate and had liquid of an unknown nature thrown in his face. It sounded like the Box was out of control.

“See me after this,” Sergeant Holmes had said to me and five others, including my friend Feliciano, shortly before that lineup. We waited, the more senior officers speculating about what was up. A different sergeant pointed us into a separate room. The administration, he told us, had ordered a second complete search of the downstairs of the Box for contraband, particularly shards of glass, in the wake of the recent incidents. This would be done one cell at a time and one inmate at a time. Some inmates—particularly because it would involve a second strip-search—were expected to resist. We were off to conduct a Nuts and Butts, in other words, with the possible need for a Hats and Bats.

We were each issued handcuffs and a flashlight, and loaded up with Cell Search/Contraband and Misbehavior Forms, as well as three big bags of “cell-extraction”/Hats and Bats gear: helmets with Plexiglas visors, stab-proof vests, knee and elbow pads, and heavy gloves. Box officers joined us, and then two sergeants. A dozen of us marched purposefully downstairs to the Box. There was action ahead, and I felt suddenly excited to have been included. Despite the ominous tone, and my better instincts, I’d countenanced enough inmate misbehavior and disrespect to feel invigorated by the thought that this is where it all stops. This is where we draw the line. We were going to follow the rules, and we were going to have our way.

By the time we’d descended to the first floor, the inmates had become very quiet. They could hear us, no doubt, but couldn’t yet see us. One of my training officers, Konoval, the first to walk into their view, set up a video camera on a tripod to record the proceedings; I had noticed that the Department often took this precaution when a use-of-force was anticipated, probably to protect itself from lawsuits. We all donned latex gloves and then, en masse, poured into the gallery.

Feliciano and I were a team, and there were three other pairs like us. Each team had been assigned a cell. I did the talking to our inmate, a Latino in his twenties. “Good morning,” I said through the bars. “We’re going to strip-frisk you, then you’re going to come out and we’re going to frisk your cell.”

The man had been through this drill two or three days before, and assented. He didn’t look angry or demented, just sort of discombobulated. He handed us his shirt, his pants, his socks, and his underwear, and then he turned, bent over, and spread his cheeks.

“Fine,” I said as he dressed. “Now, turn around and we’ll cuff you.” As the inmate put his hands behind him and through an opening in the door, Feliciano cuffed him.

“Open 105!” I called out to the officer in the bubble. The cell door opened and the inmate stepped out backward, wearing socks but no shoes. Feliciano held his handcuff chain and walked the man toward the opposite wall, where the windows had been broken by the inmate with the mop handle. Feliciano told this inmate not to turn around, then drew his baton and held it in ready position across his torso, what was called port-arms position.

I frisked the cell. It was a pigsty, with roaches crawling over the bunched-up sheets and garbage on the floor. I flipped through his notebooks; the handwriting was unexpectedly lovely. The inmate wrote in Spanish. He had also made a chess set, using toothpaste caps and squares of paper as pieces. (I had seen these games in action. Another inmate had to have a board, too, and they made moves by voice, since neither could see the other’s board.) There was a lot of pencil-written gang graffiti on the walls, but no contraband.

The frisk of our second cell, which belonged to a skinny, middle-aged man, was also uneventful. Feliciano turned up only an extra state-issued pillow, which we confiscated. Before this search was over, however, we were distracted by a commotion at the entrance to the gallery. The Box officers, Perlstein, Proctor, and McDonough, had donned full cell-extraction gear. I had seen video of the Hats and Bats outfit at the Academy; it was much more intimidating seen up close. The team was preparing to go in after an inmate named Duncan, who had refused to cooperate.

I recognized Duncan from B-block—a short black man with dreads who apparently was a perpetrator in a recent fracas in the B-block yard in which officers had been injured. Cameras had shown him throwing things at officers and egging on other inmates. He seemed to hate COs. The cell-extraction officers stood one in front of the other, the second and third holding on to the officer in front of him and the lead officer carrying a see-through riot shield. On a signal, they started moving forward in step, like a locomotive gaining speed. “Open 101!” someone shouted. Another officer pulled open the cell door and they went in on one another’s heels, the shield used to force Duncan into the back corner of the cell. It was hopeless for him, I knew—like going into battle with a rhino. Three minutes and many thuds later, the team emerged with the inmate in handcuffs and leg restraints. He somehow managed to raise a fist in defiance as they carried him upstairs to do a forcible strip search.

That was when things started getting raucous. Inmates up and down the gallery began to yell. We were “bitch-ass faggot motherfuckers.” We were getting off on looking at them naked. This whole search was just retaliation. They would file lawsuits, because we were not following directive 4910 (which said that sergeants had to be in constant supervision of a strip-frisk). One inmate began pleading to see one of the sergeants but then, when she refused to talk to him, he started berating her and Sing Sing’s two black captains as “house niggers.”

“Kill all house niggers, kill all house niggers,” he chanted, for more than fifteen minutes.

The air of pandemonium made me feel less certain that everything was under control. Somehow, this felt like the first wave of an attack. Feliciano and I were given a third cell, that of a young, thin black man, Lincoln George. I repeated the line about the strip-frisk and asked him to hand us his clothes.

“I’m not going to show you my asshole,” he stated without affect as he started to remove his shirt.

“You’ve got to,” I said.

He stopped taking the shirt off.

“I won’t do it,” he repeated.

I tried to reason with him, in a low voice. “Look, man, you see what they’re doing. They’ll do it to you. It’s not worth it. We’ll be done in like five seconds. Let’s just get it done.”

He shook his head, and said, “According to directive 4910, you could use a hand scanner instead of doing a body-cavity search.”

“This is not a body-cavity search,” I said. “Nobody’s going inside. We’re just looking from the outside.”

He shook his head. Why on earth, I wondered, would anyone choose cell extraction?

“So you’re refusing?”

“I want to speak to a sergeant.”

This was every inmate’s right. I summoned the male sergeant, who, given the din and the insults, was in no mood for a negotiation. “I’m giving you a direct order to comply with the frisk,” he said simply. I couldn’t hear the inmate’s reply.

“So you’re refusing to comply?” the sergeant said. Lincoln George nodded. The sergeant left the gallery and spoke to the extraction team.

They were swift and tough. George made little attempt to brace himself or otherwise prepare for their entrance, so it didn’t take long. He was knocked down, flattened, then hauled upstairs to be forcibly searched. We frisked his cell and found nothing.

Meanwhile, the extraction team had brought Duncan back down. They placed him in his cell, unchained him, and were on their way out when he snatched the leg chain from one officer’s hand and swung it at him, hitting him hard on the visor. The surprised team completed its exit from the cell and closed the door. Then they turned around, regrouped, and went back in again to get the leg chain. Duncan appeared shortly afterward at the door to his cell, a big scrape on one cheek. No doubt, he had untold other wounds less easy to see. Rather than defeated and injured, he looked thrilled, and once again shouted out his defiance.

The extractors took a break and then bulldozed their way into a third cell. This one I couldn’t see, but it took longer than the others and had the officers shouting, “Stop resisting! Stop resisting!” partway through. At the Academy, we’d found out that this phrase was basically a legal requirement that you shouted out to indemnify yourself when you were, for whatever reason, applying a bit of extra force. Konoval was following the team with the camera, but as the officers knew, all he could see was their backs. The inmate continued to struggle as he was carried up the stairs. I picked up half of a shattered face shield after they went by.

And then it was all done but the paperwork. The cell-extraction team came back downstairs, extracted themselves from their armor, and then gave one another hearty hugs and slaps on the back. They were sweaty and charged-up, like victorious football players. I felt the catharsis, too: Prison work filled you with pent-up aggression, and here was a thrilling release, our team coming out on top.

But as the moment faded and I picked up my gear, I paused and looked back down the gallery. It was quiet now—the sound of defeat. No weapon had been found in any cell. Perhaps, I began to suspect, none had actually been expected. It seemed reasonable to conclude that we had been sent in to make a statement about who was in charge. And I had to wonder: With the outcome never in doubt, what had we won? What did it do to a man when his work consisted of breaking the spirit of other men? And who had invented this lose-lose game, anyway?

Vivid to me, and a seeming conundrum, was the refusal of my inmate to submit to a strip-frisk. By refusing this small violation of his privacy, he’d earned himself a big violation. What could account for an action so apparently contrary to his best interests? My idea of his best interests, I later concluded, was colored by the team I was on. Eventually, it occurred to me that self-respect had required him to refuse. His stupidity began to look principled. He was renouncing his imprisonment, our authority, the entire system that had placed him there. If enough people did that together, the corrections system would come tumbling down.

Nearly ninety years ago, Thomas Mott Osborne, a politically connected prison reformer, spent a week in voluntary confinement at New York’s other famous historic prison, Auburn. The book he wrote afterward, Within Prison Walls, was an exposé of the conditions inside Auburn, and particularly inside its version of the Box, a unit of the prison that was known simply as the jail. By refusing to work in the prison’s basket-weaving shop, Osborne got himself sentenced to a night in the “jail”—a barely lit room between Auburn’s Death Row and its generator that contained eight metal cells. Prisoners there were allowed only three “gills” of water—three quarters of a pint—per day; they were not allowed any exercise, bathing, mattress, or change of clothes. Osborne conversed with his fellow inmates and soon felt sympathetic and righteous. When the warden, thinking he might have had enough after a few hours, sends the “principal keeper,” or head of the guards, to release Osborne, this is how he reacts:

Sing Sing’s SHU has no sweat box of the kind found in The Bridge on the River Kwai or Cool Hand Luke, none of the dark cells that inmates in “solitary” were subjected to prior to the middle of the twentieth century. Since then, the courts have found the extremity of that kind of treatment to constitute cruel and unusual punishment. Now the cells are slightly larger and slightly brighter, and regular access to showers and recreation, food and water, is guaranteed. But perhaps in part because inmates cannot be “broken” as quickly as they used to be, their sentences in these segregation units now drag on and on, sometimes for years. The process of breaking a man simply takes longer and costs more. Does it represent “injustice or tyranny”? That depends on your point of view: If they are not going to be put to death, the monstrous—the Lemuel Smiths—must be warehoused. Trying to extinguish the spark of the rest—the merely incorrigible, those holding on to civilization by a thread—itself feels like a monstrosity.

LINEUP ROOM

For officers, the lineup room represents the transition between the outside and the inside. There, you can rest a minute with a cup of coffee, talk with your fellow officers about work before actually going in to do it, and prepare yourself mentally. The day after the SHU extractions, CO Konoval showed his videotape in the minutes before lineup. Everyone was eager to see what had happened down in the dungeon. Nervously expecting to be transported back, I instead found the footage sort of dull: Konoval’s video, with its poor lighting and bad sound, captured none of the atmosphere of madness, the endless chanting and shouting, the high anxiety. It just looked like tough guys doing a cartoonish job, the kind of thing you might see on a crummy TV show.

In general, the pattern in lineup follows a routine. After 6:45 A.M., when we’re called to attention, come the announcements—everything from new parking rules to the schedule for upcoming sergeant tests to reminders about blood drives and retirement parties. Then, sometimes, the day’s watch commander, a lieutenant, will step up and say a few words, often a rundown of notable happenings from the shifts before.

There is a strong speechifying tendency in corrections. Another tendency, in the wake of anything gone wrong, is Monday-morning quarterbacking. Someone can always be counted on to tell the victim of some unfortunate incident how he could have handled the situation better.

My favorite watch commander was Lieutenant Goewey. A heavyset man who was somehow more blue-collar than a lot of COs—he could have been the boss of a trucking firm, to judge solely by appearance—Goewey almost always took advantage of his prerogative to speak, and his words were always wonderfully coded. He wouldn’t tell you the state police had been at Sing Sing the day before to arrest the longtime CO suspected of supplying drugs to inmates via the package room; he would simply say, “In case you haven’t heard, there’s a job opening in the package room.” He wouldn’t say he thought the previous superintendent was an idiot who neglected the security personnel in favor of programs and housekeeping; he’d just say, a couple of times a week, “Security is once again the top priority of this administration.” I found it enjoyable to read between his lines.

There was a chalkboard on the wall right behind the front gate, and one morning it read, “CO Diaz had arm broken by a con 8/19/97 and is awaiting surgery.” Following up on this, Goewey explained to us that Diaz, a well-liked officer posted to the Adjustment Committee (which conducted disciplinary hearings), had retrieved an inmate from the blocks and was placing him in the disciplinary bullpen to await a hearing when an inmate already in there went after the guy. In the struggle, the gate slammed on Diaz’s arm.

Lieutenant Goewey, in his predictably coded way, said, “The incident occurred at about two, and I didn’t hear about it until twenty minutes later. When I got there, the guy was just sitting there, happy as a clam.” There was a long pause. “Now, these days you can have a use-of-force. Whatever it takes at the time, you can do it. But twenty minutes later … I’m not saying it didn’t used to happen, but these days you can’t just knock all a guy’s teeth out and shove ’em down his throat. Twenty minutes after an incident.”

He continued: “Now, I know there’s gonna be a lot of armchair quarterbacking about this—he should have had another officer there, should have looked, that kind of thing—but it’s dead.”

In other words, Goewey had just told us: I hope you’ll forgive me for not beating the shit out of the perp who did this, and Diaz probably could have prevented it.

PSYCH UNIT

You didn’t have to work the galleries long to realize that a large proportion of inmates were mentally ill. The symptoms ranged from the fairly mild—talking to oneself, neglecting to bathe—to the severe: men who didn’t know where they were, men who set fire to their own cells, men so depressed they slashed their wrists or tried to hang themselves.

Prison, said the department’s assistant director of mental health services at the Academy, was “a hard place to be crazy.” He told us that the “last good study,” now more than ten years old, had indicated that of the state’s 70,000 inmates, 5 percent, or 3,500, were “seriously and persistently” mentally ill—people who would be in a psychiatric hospital if they weren’t in prison. But corrections had beds for only 1,000 of them. Another 10 percent, or 7,000, were under the supervision of a psychiatrist, “taking some drugs.”

Stress, he said, worsened almost any condition, and prison—obviously—is stressful. “Many people break down for the first time in prison,” the official said. In other words, prison not only made crazy people worse; it drove people crazy.

Working as COs, he said, would make us “students of human nature.” He gave us thumbnail sketches of people with schizophrenia (and symptoms like psychosis, hallucinations, delusions, and paranoia) and those with personality or mood disorders, like manic depression. Once we got to Sing Sing, however, these distinctions were never made again, at least by officers. A crazy person was a bug—slang used by both guards and inmates. Working a gallery was like sharing a crowded urban street with a higher-than-usual number of disturbed street people. Mostly, you just learned to live with the bugs. Occasionally, however, a bug went off the deep end, and—particularly if he got suicidal—would be sent to the psych unit.

Sing Sing’s PSU, or Psychiatric Satellite Unit, occupied the second floor of the Hospital Building. It was run by employees of the state Office of Mental Health (OMH) and by a handful of officers, who were there to provide security.

The door from the building’s staircase to the PSU floor was always kept locked. Half of the floor comprised offices for the various mental-health-staff members—psychiatrists, nurses, and social workers. The other half, separated by an iron gate, held the sick inmates.

The worst-off and most dangerous of these men were kept in six special high-security cells. These cells, with bars front and rear, had dense screens installed from ceiling to knee level to keep the occupants from throwing things out. Inmates assigned to them had their clothing taken away and replaced with—in severe cases—paper gowns and hospital slippers. The toilets and sinks were a single stainless-steel unit, such as were found in most newer jails and prisons but not generally in Sing Sing. The remainder of the floor’s residents—up to sixteen, who were considered less dangerous—were held in a dormitory room down the hall. They had a TV lounge across the hall, with games and newspapers, and a small room next to that where they received meals.

A very few inmates were transferred from the PSU to the state mental hospital at Marcy. This was a hard transition to make, however, since space at Marcy was limited: they had to come really close to killing themselves—slashing their wrists deeper than merely the skin, or “hanging up” in such a way that they came close to death. The only other way I ever saw an inmate get to Marcy was by making a credible threat. “I’m gonna be in here a lot of years, but I’m gonna remember you and when I get out I’m gonna find you,” he had said to a female psychiatrist. She must have believed him, because he was shipped out the next morning.

The general understanding among officers was that many inmates played a bug game—worked the system—in order to get themselves into the PSU or Marcy. They did this because life in those places, even though they were surrounded by bugs, was more tolerable than among the general population of a max. In the psych ward, you didn’t have to worry about gangs or weapons. You had more room to yourself, and there were more staff looking after you.

For the same reasons, I was always glad when Sergeant Holmes sent me to the PSU after a period on the galleries. It was quiet there, and clean; the inmates were carefully controlled, and there wasn’t much for a CO to do. Most of the time, the PSU was a relief. The most obvious evidence that things were better here was the presence of longtime officers. Because of seniority, they had their pick of easy jobs, and there always seemed to be an old-timer on duty in the PSU.

The one who was there my first day—and many times after that—was a tall, grizzled guy named Birch. He spent his days minding the staircase door and the center gate, making sure things on the floor ran the way they were supposed to, reading religious tracts, or doing crossword puzzles to pass the time. When I arrived, he was speaking through the screen of a high-security cell to a tiny Dominican named Colon, who had decorated the cell with a carpet of shredded pieces of magazine. Tassels of toilet paper festooned every bar, and some thirty wads of toilet paper had been stuck to the walls with toothpaste. I knew Colon from B-block—he had set fire to his cell and destroyed its fixtures once when I was there. As Birch walked away, Colon angrily scooped water from his toilet bowl with his hands and threw it out into the hallway.

“Oh, I know that guy,” I told Birch. “I wrote him up once for disobeying a direct order. But when I handed him the ticket, he told me I was wasting my time. He went and dug up a whole pile of tickets he’d gotten, which he said were always thrown out because he was crazy.”

“There’s a lot of guys in here like that,” Birch said. “And no, you can’t write ’em up. Keeplocking ’em just makes ’em worse. Can’t write ’em up.” He shook his head.

“Guy like you in here yesterday told me he’d written five tickets so far in his first five weeks. Five! That’s more than I probably wrote in my whole career. I’m part of the old school—we took care of things without all the paperwork then. Inmates knew that if they misbehaved, we were gonna fuck them up.” That, I should have realized right away, was how the PSU worked.

At midmorning, Officer Birch told me it was time for the lock-down inmates’ interviews with the mental-health staff, and he handed me a ring of keys. One at a time, I was to escort the inmates into a conference room where the staff was gathered, make sure they were seated, and then remain standing behind them ready to protect the staff in case of any outburst. This was a nerve-racking assignment, as I’d had no experience with any of the patients. And it was complicated by the fact that the interviews—with a psychiatrist, social worker, nurse, and two other staff members—were interesting to listen to.

First—carefully, so as not to get wet—I tried Colon. “Will you talk to the committee now?” I asked.

“Fuck, no! Fuck them!” he cried. Birch had told me that this was how he’d reacted for the past several days and that I could skip him if he did that. He’d calm down later.

The next inmate, a tall skittish man, went along without a problem. He described to the psychiatrist how two demon COs were using secret symbols to communicate with space beings who landed on the roof of A-block. The COs intended to jinx him with voodoo. Glancing up at me with a hint of a smile, the psychiatrist suggested to the inmate that he consider taking Haldol (an antipsychotic medication). The man shook his head. “Once you start takin’ that shit …” he muttered.

The psychiatrist then proposed a drug that was milder, and the others at the big table nodded. Still the man demurred. But then the doctor laid it on: “Wouldn’t you take antibiotics for a cold or if you had a small infection?” he asked.

The inmate said he would.

“Well, this is like an infection in your head,” said the shrink. The inmate finally agreed to the daily medication.

I had already guarded the next inmate that morning, during a one-on-one interview with a caseworker in her office. He was a heavyset black man who had seemed calm during the meeting. As soon as he left the office, though, he’d begun to speak loudly and incomprehensibly about Mike Tyson. Now, he was calm during his meeting with the committee.

The psychiatrist, reading from a folder in front of him, said he would pretend to do a cross-examination. Was that all right? Sure, said the inmate.

“It says here you sometimes scream when you’re all by yourself. Is that true?”

“Yes.”

“That you have an entirely new personality lately?”

“Yes.”

“That you often feel very angry, and go around yelling at everyone?”

“Yes.”

“That you think you’re the fifth Beatle?”

“No! That’s not true!”

The psychiatrist smiled. “I might have made that one up,” he said. Others on the committee chuckled.

“That you break things in your cell.”

“True.”

The inmate agreed to a new course of medication, much to the committee’s satisfaction. This was their main purpose, it appeared: to find a way to manage the inmates such that, with daily meds, they could return to the general population. Guard slang for these meds was bug juice or the cure, but everyone knew it was not a cure. (Many inmates believed that taking them would addle your brain permanently.) The PSU was a holding tank, not a place where people improved. No one, as far as I could see, improved in prison. It took weeks for an inmate in the general population to get an appointment with a therapist, and the wait between appointments, once a relationship had been established, also seemed to be weeks.

His interview concluded, the inmate left the room. The minute I closed the meeting room door, just as before, he resumed his rant: “Mike Tyson fucked ’em up, and now they’ll pay him, they’ll turn it around,” he bellowed. I was relieved to get him back in his cell.

The next two trips to the conference room passed without incident, but the interviews continued to enlighten me. One inmate, a Latino, seemed candid when describing the drugs he’d done in prison: marijuana, crack, powder heroin, Valium. I was surprised at the variety, but the committee wasn’t. And he knew the lines to use to impress them. (“But I know it’s important to stop drugs so that I can get my life together and, if I’m fortunate enough to earn parole, be a good provider to my kids.”) The next inmate, who was white, seemed more lost. He rambled on about the people who wanted to get him and a threatening letter he’d received. The committee seemed to know all about it. Abruptly changing the subject, a counselor said, “And you know what to stay away from, right?”

“Homosexuals, drugs, dice …” he began.

“Gangs, gambling, gays, and drugs,” she said.

“Right.”

Gays? I wondered. It sounded more like a political point of view than a therapeutic strategy. But I couldn’t ask. My radio squawked, as it often did, and the inmate glanced back at me nervously.

“Could you ask him to leave the room?” he said to the committee members. The psychiatrist nodded and gestured for me to leave.

And so the inmates went in and out, doing kind of a shuffle, perhaps a by-product of medication, perhaps because we had confiscated their shoelaces so they couldn’t hang themselves. Regardless, they seemed authentically sick to me.

They saved the worst inmate for last. Massey was a medium-size, twenty-something black man who was zoned out, like a zombie. Arriving at his chair, he wouldn’t take his seat. “Sit down now!” commanded the psychiatrist strictly and, very slowly, the man did. “Stand right behind him,” a female therapist whispered to me. “He might get up.” I don’t remember much about his interview because I was too busy worrying about what I would do if Massey did get up. I placed one of my hands on the end of my baton. There were general questions about the voices Massey heard, about why he wouldn’t take the medication. “That’s all for now,” said the psychiatrist.

Massey didn’t budge.

“I said we’re done now. You should leave the room,” the psychiatrist directed firmly. I removed my baton from its ring and walked into view of Massey. Slowly he stood. I held open the door. Slowly he moved through it. He seemed unresponsive to normal stimuli, sealed off in his own world. The way to his cell was straight ahead, but he turned right, toward the center gate, which led to the civilian offices. Birch was sitting beyond the gate. “Hey!” I yelled.

Massey bent for a drink at a fountain, then stood up and continued his walk. The center gate wasn’t closed as it was supposed to be.

“Stop right there!” I shouted, but Massey plodded on. Birch rose to his feet and stretched his arms across the open gate. “Go back to your cell!” he ordered. Massey walked on in slow motion, right into Birch, trying to push him out of the way.

In a split second, Birch had a hand around Massey’s throat, and I found myself joining him in pushing the inmate against the wall. Birch punched him in the stomach, yelled angrily, then punched him again. I twisted one of his hands into an ordinarily painful aikido grip, but Massey was oblivious. He stared blankly and struggled to get loose. With difficulty, we began moving him back toward his cell. Just then, a huge keeplock officer from B-block named Phelan appeared—in the nick of time, as far as I was concerned, for Massey was surprisingly powerful. With Phelan, we moved him to the door of his cell, but there progress ceased, for Massey grabbed the bars and held on like a crab. It took ten or fifteen seconds for the three of us to pry him loose, during which Birch’s gold watch clattered to the floor. Even after we placed him on his cot, Massey got up and resumed a somnambulant march toward the door.

Phelan lifted him into the air and slammed him against the cell’s metal wall.

“Stop all this bug-game shit!” he yelled.

The inmate seemed insensate. No emotion passed across his face, no sign of fear or pain. Bam! Phelan slammed him up against the wall again. This time Massey looked more discouraged and didn’t try to stand. We locked him in and dusted ourselves off.

“Massey playin’ a bug game,” said Birch. He’d been in and out much of the past two months, he said, but he wasn’t usually this bad.

It was my first use-of-force incident, and the experience was heady. I paused to gather my thoughts. Department policy on this was quite strict. I was in charge of the PSU logbook, so I went to make an entry.

“What’re you doing?” asked Birch.

“Logging it.”

“Don’t log it. That’s a waste of time. Won’t no punishment come out of it for him, ’cause he’s a bug. It’s just a lot of paperwork we’d all three have to do. And Phelan’s gone now. Forget it.”

I held the pen poised above the paper for a moment, then put it down. I didn’t want to alienate Birch. What he said was like a lot of things about prison: brutal, but reasonable under the circumstances.

Sitting in chairs alongside the six psych-unit cells most days, twenty-four hours a day, were the officers assigned to two kinds of special watch: suicide watch and drug watch. Suicide watch was clear enough. Inmates thought to be on the verge of killing themselves had to be closely observed until they were deemed out of danger. Drug watch was similar but less glamorous. Any inmate who was thought to have swallowed some drug in a packet—in hopes of not getting caught with it—was placed for seventy-two hours in a cell with the taps and toilet water turned off. He was allowed no underwear, only a paper gown. The observing officer was provided with latex gloves and a tongue depressor. In case of an inmate bowel movement that yielded some “prize,” he was to call a sergeant.

I spent two shifts and some overtime watching an inmate from Tappan who an officer had seen swallowing something white during a routine pat-frisk. In trying to stop him, the officer had broken his dental plate, the inmate complained; and all he’d been trying to swallow anyway, he said, was a written note. He’d been in there almost two days when I began, and had completed almost three when I finished, and still no action. His defeat of the system, after seventy-two hours, had much to do with the fact that he wouldn’t eat anything from the food trays that were brought to him three times a day. He did, however, drink water, and the area reeked of urine stagnating in the toilet bowl. The job was killingly dull, and I would have been likely to drift off to sleep if not for one fellow officer’s warning that an inmate he had once watched had had a movement, all right, but had then quickly reswallowed the packet of contraband before the officer could open up the cell.

Much more often, I was assigned to suicide watch, euphemistically known in the Department as special watch. When you arrived, you received no specific information about the inmate under observation—just the special-watch logbook, the only reading material the officer was allowed to have. One summer day, strung out from the blocks, I settled with relief into the special-watch chair and peered into the cell. My inmate, Morales, was fast asleep. My sole duty was to make an entry, every fifteen minutes, describing what Morales was up to. “Morales asleep,” I wrote several times.

The logbook went back two years. I decided to read the whole thing. The majority of entries described inmates snoring, lying on their sides, and turning over. But there were also some startling entries. One officer had accompanied a suicidal inmate to nearby St. Agnes Hospital:

Another series of entries was from the cell next to the one I was watching:

7:00 A.M.	CO J Carmody on duty on PSU special watch cell #20 Inmate Rivera, Richard 94A5932. Inmate appears to be sleeping. All appears secure at this time.
7:30	Inmate appears to be sleeping ATT.
8:00	Inmate appears to be sleeping ATT.
9:00	Inmate Rivera is awake ATT. Inmate state that he is not eating. He is not hungry.
9:30	Inmate states that he is not going to eat or talk to anyone. He states he is going to jump off sink and break his neck on the bed. Inmate is standing on sink. Obeys order to get down.
9:40	Nurse in to talk to Inmate.
9:55	Rivera out to talk to PSU staff.
10:15	Rivera back in cell.
10:30	All appears secure ATT.
11:00	All appears secure ATT.
11:05	lunch served. Inmate Rivera refuses to eat.
11:30	All appears secure ATT.
12:00	All appears secure ATT.
12:30	All appears secure ATT.
12:45	Inmate eating what appears to be feces. OMH [Office of Mental Health] notified.
1:15	Inmate has a pile of feces on the floor and is at times eating it. OMH staff notified.
1:30	All appears secure ATT.
2:00	Inmate jumping off sink against the wall. OMH notified.
2:05	Inmate claims he injured his right arm. OMH notified.
2:30	All appears secure ATT.
3:00	All appears secure ATT.
3:20	Inmate states to me he wants to fight. States he wants to “set it off.”
3:45	Nurse speaking to Inmate Rivera.
3:50	Inmate Rivera eating dinner now.
4:00	All appears secure ATT.
4:20	Inmate jumping off sink onto bunk. Refused order to stop. OMH notified.
4:30	Inmate jumping off sink onto bunk, bounced off north wall, fell on bunk and landed on floor. Claims he can’t move. OMH notified. Nurse Dennis and CO’s Smith and Copper responded.
4:40	Inmate observed moving his legs and body off floor.
5:00	Inmate continues to lay on floor.
5:15	Inmate stood up and then lay back on floor.
5:20	Inmate makes medical history. He’s now cured. Inmate walking around. Inmate threw tray on gallery.
6:00	All appears secure ATT.
6:15	Sgt. Carrigan speaking to Rivera.
6:30	All appears secure ATT.
7:00	All appears secure ATT.
7:15	Inmate standing on sink. States he is going to jump onto edge of bed and break his neck. Given order to come down. Inmate complies.
7:20	Inmate standing on sink. States he is going to kill himself.
7:45	Nurse talking to Rivera.
8:00	All appears secure ATT.
8:55	Inmate issued mattress cover, socks and t-shirt per OMH Nurse Whit.
9:30	All appears secure ATT.
10:00	All appears secure ATT.
10:30	All appears secure ATT.

Morales slept almost the entire shift, rising near the end only to ask for a cigarette. He even slept through the day’s only excitement, when an inmate down the hall managed to cut both his wrists with the blade from a disposable razor he’d somehow smuggled in. The officer observing him called a nurse and the sergeant. The nurse, noting that the slashes were only superficial, just had the inmate stick his arms out through the bars so she could clean them up and put on antiseptic and bandages. The sergeant, annoyed to have been called up for nothing, advised the inmate, “Next time, cut the long way. It works a lot better.”

By the next day, I’d learned more about Morales. Some of his earlier stays in the PSU had been recorded in this same logbook. He’d frequently been suicidal, and was prone to self-mutilation. A female officer had logged an entry about him masturbating openly. Another officer must have remarked on it to him, she wrote, because when she came back on duty, the next day he was “irate” that she had written it down. Poor guy. He had been observed singing “White Christmas” and dragging a plastic disposable cup top around his cell with a string, calling it his “car.” Less benignly, he had pried up and swallowed three pieces of floor tile, and used another shard of the tile to make cuts across his leg and wrist and, apparently, “a blood-filled hole in chest.”

I watched the indistinct form of the forty-something Puerto Rican through the screen as he turned in bed and sat up on his mattress. I could tell he had a beard and mustache and a bit of a belly, but all I could really see unobstructed were his feet and pale, thin calves. I didn’t know what incident had caused him to be moved from the fourth floor of 5-Building (the psych floor) over to here, but usually it was a suicide attempt. He confirmed this after lunch, when he ran out of matches and I offered him a light. He bent down near the bars to show me the slashes across his right forearm that he had made with a tin-can top. They looked deeper than most. Later, he even lay on the floor so that I could see, below the screen, the still-red scars of previous self-inflicted wounds—a gash near the jugular made with another piece of floor tile, and the now-healed hole in his chest.

It was the pressure of prison, Morales told me, that caused him to hurt himself. Gangs were especially hard on him—they took advantage of the mentally ill by sending them on risky assignments. If they got caught by the COs, their mental status was a kind of indemnity. He said he’d do whatever it took to get out of Sing Sing.

“Including acting crazy?”

“It ain’t hard to act crazy when you are crazy, CO,” he said.

“Hmm.”

“Hey, it wasn’t my choice to be here. The guy I killed, you’d probably want to kill him, too. He beat up women. ’Course I was fucked-up at the time.”

“What do you mean—on drugs?”

“Drugs and alcohol. But I took the ASAT [Alcohol and Substance Abuse Treatment] course, which I think will help me stay off. You know what I really want, though? Chinese food. Chinese or Thai. I want some fried rice. What I’d do for fried rice.”

Two days earlier, according to the logbook, Morales had told his guard that the only way out was to kill himself. There was no way to go home or to see his family. They wanted him to kill himself and even said so, now that his mother had died. He was laughing out loud “for no apparent reason,” hitting himself in the head with an open palm.

But sometime between then and now, he’d been told something miraculous: He would be shipped to Marcy in two days. That had calmed him down considerably. During the second-degree murder bid that had started in 1984 and also taken him to Attica and Wende, he’d already been to Marcy four times, he said. It was good there: no gangs, a movie every day, four-man rooms with the doors unlocked during the day, no COs per se. There were punishments—they’d put you in restraints or “stick you in the ass” with a tranquilizing injection—but it was freer there.

“But aren’t there only bugs to talk to?” I asked.

No, he said, and he knew a lot of guys there.

He showed me his “inmate accounts” statement—on which inmates keep track of how much they can spend in the commissary—and told me he bet I’d never seen one like this. And I hadn’t. He had a negative balance of more than a hundred dollars.

“How can you have a negative balance?” I asked. “They gave you credit?”

“No, man. It’s my tickets. I had twenty-three Tier Two and Tier Three tickets in the last year.” Each of these serious infractions, regardless of the disposition, resulted in a five-dollar charge to the inmate’s account.

“For what?”

“Oh, for drinking paint, for tearing my sink out of the wall, for hurting myself. They’re not fair, man. You shouldn’t get charged when you’re sick in the head.”

Drinking paint? Even if you did it with the conscious goal of getting yourself away from the general population, you really did have to be sick to drink paint or swallow shards of floor tile.

I told Morales about the death, the night before, of Princess Diana and about the new MetroCards that were taking the place of tokens on the New York City subways. He asked me for lights for his cigarettes, and when my matches ran low, he showed me how to tear them carefully up the middle, making two matches out of one. Finally, he suggested that we play chess. I found the painted Masonite board and a box of plastic pieces in the lounge; we balanced the board carefully on the cell’s food slot, near the floor.

Morales was a competent chess player. We each won a game and then, in excitement, because I was ahead in the third, I bumped the board and tipped it over. Whoops. Birch dropped by, warning me that many sergeants objected to officers playing games with inmates. But then he offered to warn me by rapping on the window if anyone approached. Morales assured me that when he heard the rapping, he’d take the chessboard off the bars and place it under his bunk. I heard a tapping on the window after lunch and told Morales the moment had come. It took a moment for it to register, though, and when it did, he tipped the pieces all over the floor of the cell—an instant before Sergeant Holmes rounded the corner. Fortunately, the screen obstructed Holmes’s view of the mess. He initialed the logbook and was gone.

Our subsequent games were constantly interrupted by inmate Auguste, in the next cell down. Auguste was a thin black man who greeted every officer that passed, no matter what time of day, with “Top of the morning to you, sir!” In one of the more macabre tableaux I witnessed in the prison, he would stand in the middle of his cell, arms outstretched, head back, singing favorite lines from “New York, New York”: “‘If I can make it there, I’ll make it anywhere.’” Another time, sounding like one of the homeless men in Manhattan who wait outside fancy restaurants late at night and flatter emerging patrons before asking for a handout, he had told me, “You look like Robert Redford!” To the nurse, I heard him say, “You’re a combination of Grace Kelly and Princess Diana!”

Another time, though, I saw Auguste stop singing as though suddenly possessed and then begin to mime savagely beating someone on the floor, as though with a hammer or hatchet. So much for the sweet old nutcase.

Today he was singing, “O beautiful for spacious skies,” again and again, until Morales hollered, “Knock it off! Will you fuckin’ knock it off?” A long silence followed, while Auguste’s brain rebooted. When it came back on-line, he was singing the sixties pop hit “Sugar, Sugar.” Then I noticed he was out of his cell. Inmates whom the shrinks judged to be making progress were allowed out for a few hours a day; this was called rec. Auguste came to watch our game.

“The Archies, right?” I asked as he hummed near me.

“Yes, sir. I was their bass player.”

Morales tried to cadge some tobacco off Auguste, who obliged, but in return he began to lecture Morales about Egypt and the Pharaohs and how the white man rules but the black man is really in charge because Jesus was black and—

“Stop that bullshit!” screamed Morales.

“Yes, Master, yes,” said Auguste, and hurried away.

I wished Morales luck and we knocked knuckles, the way inmates did with each other. I could do it because he was out of there, bound for Marcy, and I’d never see him again.

VISIT ROOM

It was easy to forget when you worked at Sing Sing that all the inmates there were, essentially, missing from someplace else. Outside the walls, however, they were still fathers, sons, brothers, and husbands—mainly of poor people from New York City. In being sent to prison, they had no doubt let people down; some who loved them no longer wanted to see them. But they were missed by many others, and every day of the week these people found their way to the prison via bus, car, train, and taxi. They submitted to searches of their person and property and subjected themselves to long waits in order to spend a short time in Sing Sing’s Visit Room.

The Visit Room constituted a sort of breach in the wall between the hermetic world of the prison and the universe outside. In it, an inmate could try to reconnect to the real world and prior life, could try to salve the wound of imprisonment. A visitor could contemplate, with more perspective than any prison employee, the effects of incarceration and the prospects of life after it. The Visit Room was about catching up, reconnecting, and looking ahead, about a woman’s touch and a child’s chatter.

I worked the Visit Room with Colton, wearing the dress blues that officers had to put on for any post that brought them into contact with the general public. We sat behind a wide desk on a raised platform and surveyed the expansive, cafeterialike space. The back of the room was lined with vending machines, and between those and us were carefully aligned rows of tables and chairs, identified by letters that hung from the ceiling. To our left was an enclosed play area for kids. Behind it were small offices for an inmate photographer, who snapped keepsake Polaroid pictures, and a counselor who could help with matters such as weddings. (Inmates were allowed to get married in prison, with the permission of the superintendent, and thereby qualify for an eventual conjugal visit.) The wall to our right was a series of picture windows—perhaps intended to offer a commanding view of the Hudson River, but now marred by a blue heat-reflective film applied to the glass to keep afternoon sun from overheating the room. Beyond, coils of concertina wire topping a mesh fence further obscured the vista.

To our immediate right was the door through which visitors entered after presenting I.D., checking their belongings, and passing through a metal detector. We pointed toward their choice of seating—either the tables, which were surrounded by four plastic chairs, or rows of chairs near the window, where they could sit next to an inmate. Inmates arrived through a separate door, to our immediate left. Once they had checked in with us, we pointed them to their visitor. If a visitor was still waiting after an hour—this was common—we would call the blocks to learn the reason for the holdup. Occasionally, it was an officer’s fault: The gallery officer might have failed to find the inmate and then forgotten to follow up, or someone might have forgotten to notify the gallery officer. But often the problem was with the inmates—they could take forever with showering, shaving, and coiffing, trying to get together the perfect self-presentation.

Colton was in a rotten mood, hardly talking, clearly homesick and hating Sing Sing. “How’s it going?” I asked anyway. “I could live without it,” he replied. He seemed uninterested in and even averse to the dramas unfolding before us, but I was fascinated. If you’d ever wondered about inmates’ lives outside prison, here were some of the missing pieces.

I watched a young woman who came in, found her table, put her head down, and went to sleep while awaiting her beau. He awakened her with a kiss—Prince Charming—and I wondered whether they always did it that way. Then there was another couple whose visit started icily. She practically put an arm up to keep him from hugging her, he settled for a squeeze of the hand, then the two retired to the side-by-side seats in the back of the room. Three hours later, I noticed, they were kissing passionately, the freeze having thawed.

On the other side of the room sat an aging couple, there to see … a son? Almost every visit began with an embrace, but some beginnings were shy or tentative. The son and his parents touched only arms, not chests; he might have given his mother the briefest of kisses. Or was she a foster mother? Was he a stepdad?

One inmate was thronged by three little kids the moment he left our desk. They jumped around him and held on to his legs as he made his way toward their mother—his wife? or was it his sister?—who tried to clear a space for him at the table amidst the crayons and coloring books. It made you happy, this sight, but also very, very sad.

Several regular officers worked the room with us. Since Colton was incommunicado, I began chatting with a regular named Eveillard, who was born in Haiti, he said. Eveillard, balding and with a dirty shirt, had been deflecting the barbs of some of the American-born officers, with limited success. He seemed glad to talk to someone who wasn’t going to make fun of him. As he was sealing an envelope, he told me the story behind it. He had just returned from a vacation in Santo Domingo, capital of the Dominican Republic, which shares the island of Hispaniola with Haiti. I had never met anyone who vacationed in Santo Domingo, I said. Got to go! he said enthusiastically. He had met a beautiful woman there and had fallen in love. He spoke some Spanish, and that was how they had communicated, but he could not write Spanish. Fortunately, a porter—he gestured toward a young inmate cleaning the children’s play area—had written a love letter for him in Spanish.

Eveillard had me walk around the room with him. A boy was about to follow his father into the inmates’ bathroom. “Sorry, that’s not allowed,” Eveillard told them. You had to keep an eye on them, he emphasized. Though visitors were screened with a metal detector, they could not be pat-frisked unless there was reason to suspect them, and this was one way drugs came into the facility. A woman could have some dope in a packet in her bra, the man could swallow it, and—voilà. And there were lesser scams, too.

“You know they can’t have sneakers worth more than fifty dollars, right? Well, their homeboy comes in wearing new Air Jordans. The inmate takes off his old sneakers, and they switch ’em under the table. Maybe we’ll catch the inmate on his way out, but maybe we won’t.” I thought I would probably notice an inmate wearing Air Jordans.

It had also happened that a visitor wearing a double layer of clothes left one layer in the bathroom for his inmate friend. The inmate, dressed in civvies, might try to walk right out of the Visit Room to the street at the end of the day. Of course, there were procedures in place to prevent this—an ultraviolet stamp applied to the visitor’s arm when he entered and then checked when he left was one of them—but you had to be careful. An inmate had escaped from the Rikers Island Visit Room that same summer, despite the many fail-safes.

With Eveillard, I stopped at a table where a young woman in a red dress had left her chair and was sitting in the lap of the inmate. “Not allowed!” Eveillard said, making a loud tsking noise. Reluctantly, and slowly, she moved. As long as each person stayed in his or her chair, feet on the floor, with no intimate touching besides kisses, we would leave them alone. But the battle against lust required constant oversight: I had to order the same woman off the inmate’s lap an hour later. Eveillard told me he’d actually had to interrupt an act of standing intercourse a few months before. The Visit Room had an outdoor annex for warm days, and the couple had been standing behind some of the playground equipment—not exactly family entertainment.

There was also a special sealed-off area provided for no-contact visits. This was the kind of visit space that movies and television made out to be the norm, with partitions, windows, and telephone receivers, and with both parties anguished because touching was impossible. The reality, at least in Sing Sing, was different. Inmate and visitor were kept separated only if one of them requested it. Just the week before, Eveillard said, a woman had arrived and requested a no-contact visit—she was going to tell her husband she wanted a divorce, and feared his reaction. As anticipated, he exploded, and officers had to restrain him.

Another reason to stay alert was that, instead of a disintegrating relationship, an inmate might have an extra one. Every longtime officer seemed to have witnessed a wife arriving when an inmate’s girlfriend was already there, or vice versa. Fireworks were guaranteed.

Eveillard had worked the Visit Room for a long time and liked it. I did, too, because I didn’t feel as much in prison myself here, and I got to witness positive interactions instead of the customary conflictual ones. But, like a great many other officers who worked the Visit Room, Eveillard found one aspect of this duty really galling: the number of attractive young women who visited inmates.

“You saw the one in the red dress. And look at that one!” Eveillard hissed under his breath. “What does she see in him? What can he do for her? Nothing!”

I found the presence of attractive young women here curious but not vexing. But to Eveillard it was infuriating, evidence of female delusion and divine injustice. “You see her?” he said quietly of a woman holding hands with an inmate at a table. I recognized the inmate from B-block. He was frequently called out for visits. “She comes here after working a night shift, almost every day. To spend her time here! She is doing his time for him!” I knew what Eveillard meant. There was almost no limit to the number of visits an inmate could have, even if he was keeplocked or in the Box. As long as his visitor was there, he could be out of his cell from around 8:30 A.M. to 2:45 P.M., Monday through Friday (and alternate weekends), enjoying the relatively pleasant environment.

He pointed out another woman, this one pregnant, accompanied by a small child and looking very happy to see her inmate. “See her? That’s his wife! She met him seven years ago, when she came here with a friend who was visiting another inmate. First they got married. Then they did the FRP [Family Reunion Program—a program allowing for occasional conjugal visits]. And now she’s pregnant again. Unbelievable!”

“That is strange,” I had to agree. “Maybe she just likes having a husband who isn’t around.”

“But how can he support her?” he asked, exasperated.

Well, there was welfare, and a few inmates had means, but it was mostly a mystery. I wondered what kind of love the woman felt for the inmate. Was it romantic—the desire for something you could never have? Was it practical—a way to raise children without interference? The COs couldn’t figure it out, because these men could never support the women, and the goal of solvency animated officers’ entire lives.

On the other hand, I had gotten to know such a woman while doing research for a magazine article I’d written about a hatchet murderer. The killer had secretly created and then marketed software from within the Minnesota state prison system while participating in a vocational course that allowed him access to the Internet. This woman had had a crush on him since she was a teenager, long before he committed the murder. So strong was her attraction that when the inmate was paroled, seventeen years after his conviction, she divorced her husband (the father of their two kids) and took up with him.

“My whole attitude was, it really didn’t matter,” she had told me of the murder and conviction, which she considered one-of-a-kind occurrences brought about by a fluky convergence of factors. And practicality, she felt, should always take a backseat to true love.

Since many of the women in the Visit Room were from the ghetto or at least the poor side of town, the absence of loved ones due to incarceration was a fact of life in their world, something they had to accommodate. A line in the movie Birdman of Alcatraz seemed to capture this situation exactly. The “birdman” murderer, Robert Stroud, had been transferred to Alcatraz and away from a midwestern woman he had met by mail while in Leaven-worth. The woman, whom he had married, showed up one day at Alcatraz to visit him, and Stroud, speaking for every person who had ever puzzled over this question, demanded to know why on earth she had come all that way.

“Because,” she said, “you’re the only life I have.”

I returned to sit at the desk with Colton. Both of us were tired. But I got the feeling that exhaustion made him more “cop” and me less “cop.” We finished up our paperwork, and at 2:30 P.M. Colton announced through the microphone that all visits had to end; everyone had to be out of the room by 2:45 P.M. As the minutes ticked off, little girls clasped their daddies’ necks, lovers hugged as though the embrace had to last through all eternity, and an old woman got teary-eyed. The positive side of visits was made tragic by the truth that prison, over time, eroded or erased practically all relationships. Despite what I had seen in Minnesota, I knew that precious few survived. People on the outside moved or met new people or died. They moved on. Did Colton share any of these thoughts? As we stood up to herd everybody out, I couldn’t help myself. I gestured out at the sea of emotion and asked, “Does it make you a little homesick?”

“Oh sure,” said Colton wryly. “It’s a regular Hallmark card.”

I stopped at my local garage to get my car inspected on my way home. It was a small place near the tracks in Yonkers. The hardworking owner, Marty, looked upset this evening. As I sat in the waiting room, I overheard him telling another customer that something had happened to an elderly friend of his.

“Harry’s retired, and he’s walking home with a toolbox last night after doing some volunteer work at his church. And these guys knock him down, beat him up, send him to the hospital. Just to get a couple tools.” He shook his head in disgust.

That brought me down to earth, rechanneled some of my sympathy. I know those guys, I wanted to tell Marty—I spend every day with them.

It was all about absence, wasn’t it—the absence of imprisoned men from the lives of the people who loved them; the absence of love in prison. And also—what you could never forget—the absence in the hearts of decent people, the holes that criminals punched in their lives, the absence of the things they took: money, peace of mind, health, and entire lives, because they were selfish or sick or scared or just couldn’t wait.

WALLPOST

The old chair was comfortable, the view stupendous, the feeling of being left alone delicious.

I was up there by myself—just me, my guns, my newspaper, and the toilet—working Wallpost 18.

It would be satisfying to a closet sniper, this job, because he could spend long hours playing out scenarios of whom he might have to fire at, with which weapon, and under what circumstance. It was satisfying to me because, again, it was a reprieve from the noise and stress of the blocks. The old prison wall was studded with nine of these towers; there was a total of eighteen towers, including the ugly new square ones around Tappan. I loved the architecture: Sing Sing’s old octagonal towers were the prison’s main emblem, the image on the souvenir history booklet, union key chains, and the coffee cups and T-shirts sold by enterprising officers in the parking lot on payday. Each tower had a catwalk around it, with spotlights affixed to the railing, and the feeling inside was of a cozy bungalow. I loved the breeze blowing through, and my privileged position firmly astride the prison wall, with both sides in plain sight.

All of the actively used wallposts contained a small arsenal. The gun rack, set between two of the eight windows, held a Remington shotgun, a Colt AR-15 assault rifle, a tear-gas gun, and many rounds of ammunition. Around my waist was a belt and holster with a Smith & Wesson .38 Special revolver. Across the room were some chemical-agent canisters in a special vest, next to a riot helmet and megaphone.

There was nothing much to do, and yet you had to stay alert: That was the joy and difficulty of a day in a wall tower. But mostly it was a joy—I had wanted to run up and kiss Sergeant Holmes when he assigned it to me. New officers did not get up here very often. The regular, I found out, was on a two-week vacation.

You enter the wall tower through an ancient gate outside the prison wall. The towers were considered the facility’s last line of defense, so they were to be inaccessible from within the prison. To get the key, you presented yourself at the gate and waited for the officer you were relieving to drop the key down in a bucket on a rope. The key itself was marvelous—the oldest I’d seen in Sing Sing, thin and short, with two circles cut out of the grip and the edges softened by a million touches. Sargent & Greenleaf Co., it read on the grip, Rochester, N.Y. No. 101. I would later see a similar one in a display case at the retired federal prison on Alcatraz Island, in San Francisco Bay; that one dated to 1909.

Inside the tower was a corroded iron spiral staircase. One complete turn took you up some twenty-five feet to the metal hatch in the middle of the floor above. By the time you arrived, the officer who was headed home had lifted the hatch so you could climb in. You exchanged pleasantries and the key, which he used to let himself out and then placed back in the bucket for you to pull up with the rope. Then you were secure, ready to start your shift.

Sing Sing had three “sally ports,” or vehicle passages, to the outside world, and Wallpost 18 sat above one of them. The port had two huge sliding metal gates which, for security reasons, were controlled not from the ground but from my tower. A vehicle entering or leaving the prison would pass through one gate, stop over a submerged inspection bay, and wait for inspection and clearance for passage from officers on the ground, who signaled me when all was clear. Then I would turn one of the big black switches on my control panel, the other gate would open, and the vehicle would proceed. The simple rule I had to remember was to always close one gate before opening the other.

Fortunately, this sally port was used mainly for official vehicles—prison vans, state-police cars, ambulances—and it was a weekend day, so there wasn’t much traffic. I could relax a little. Using binoculars, I watched a sailboat regatta down by the Tappan Zee Bridge and saw the slowly moving traffic on the bridge above. I scanned the facility, land of a zillion red bricks. And, resting my eyes, I watched a flock of geese exploring the chapel lawn in front of me. That particular swath of lawn was also pictured in a photograph taped to the wall next to the window. A square yard of it was indicated with Magic Marker. That was where I was to aim any warning shots.

I checked the weapons, counted the ammunition, made the required phone call to the watch commander to say that everything was okay. I flushed the toilet: It was a steel commode/basin combination, just like the ones in the psych unit. A jury-rigged burner and pot also looked inspired by, if not commandeered from, inmate facilities. I glanced into the ambulance log. One seemed to enter the facility every three or four days, on average. A bunch of memos were stuffed into a clipboard. One was headed DISABLING OF HELICOPTERS. First you were to fire into the rear rotor, it directed. Only after that, because of the high risk of explosion, were you to shoot into the engine cowling. Third, after warning shots, you could “fire to disable any inmates who may approach.” But only if the exploding helicopter hadn’t already wiped all of us out, I supposed.

A second memo, from a captain, seemed aimed at shaking up the tower personnel, who were no doubt a bastion of complacency. “It must be realize [sic] by all staff that the perimeter is the first and last lines [sic] of defense in maintaining the high degree of security necessary for the secure operation of a maximum security Facility,” he wrote. “We all must be cognizant of the close proximity of this Facility to NYC which is home to a major part of our population …” Blah blah blah.

Another memo, four years old, described the Family Reunion Program, probably soon after its inauguration. Entrance to the family-visit trailers was through the sally port at Wallpost 15, where I would work later. Each unit had an outdoor grill and picnic table, and they shared a swing set; inside, I was told, there was a television, a kitchen, and separate sleeping areas for kids and adults. Married inmates on good behavior were eligible to stay there every few months. The Felon Reproduction Program, some officers called it.

On the memo, a wall-tower officer had penned in a telling editorial change in one sentence. “Purpose: To provide for a Family Reunion Program which helps preserve, enhance, and strengthen family ties that have been disrupted as a result of incarceration.” The word incarceration had been crossed out, and handwritten in its place was the word individual. Family disruption wasn’t caused by incarceration, in other words; it was caused by actions of the individual that resulted in incarceration. The distinction was important to officers, who wanted no personal responsibility for the harmful effects of the system.

Down on the street outside the wall, the roach coach honked its horn. I stepped out onto the catwalk and hollered to the driver: “Pizza and coffee?” I pointed to the bucket on the rope, and he nodded. I lowered a five-dollar bill to him and, soon after, pulled up my lunch and my change.

As I ate, I read CPO Family, the magazine of the Correctional Peace Officers Foundation, a group that offered money and support to the families of slain correction officers. (I joined this organization.) The best article was written by a New York State officer.

“What would the average citizen say if it were proposed that police officers be assigned to a neighborhood which was inhabited by no one but criminals and those officers would be unarmed, patrol on foot and be heavily outnumbered?” asked Donald E. Premo, Jr. “My beat is totally inhabited by convicted felons who, by definition, are people who tend to break laws, rules, and regulations. I am outnumbered by as much as 20, 30, and even 40 to 1 at various times during my workday, and, contrary to popular belief, I work without a sidearm. In short, my neck is on the line every minute of every day.”

Premo had a good point, I thought, but with the blossoming cynicism of a few weeks in Sing Sing’s blocks, I could see he’d understated his case. Twenty, thirty, even forty to one? How about coming to visit me in A-block or B-block? How about 150 to one?

Looking down the hill, I could see a corner of the A-block yard. Guards who worked towers over a yard had a lot of responsibility. The officers on the ground depended on them for support in case of a disturbance, and yards were a frequent site of trouble. Sometimes, as we’d been told at the Academy, an officer could stop a fight just by turning on his PA system and loudly sliding a shotgun shell into its chamber. Some officers were not shy about actually firing. One OJT who’d been at Clinton briefly told me an officer there had recently shot an inmate’s finger off, presumably while aiming for something more meaty.

My tower was not responsible for the A-block yard, for which I was glad, because even my partial view of it reminded me of the death of George Jackson, the Black Panther and author of Soledad Brother, a collection of letters from prison. Jackson and two other “Soledad brothers” had been accused of helping beat to death a white correction officer at the California prison on January 16, 1970. (Three days earlier, a white tower guard at Soledad had shot and killed three black inmates.) Just before the opening of his murder trial, Jackson was shot and killed by a tower guard at San Quentin, where he had been transferred. The authorities said he was shot because he was armed and attempting to escape. “No Black person,” wrote the novelist James Baldwin, “will ever believe that George Jackson died the way they tell us he did.”

The trash can on the outside catwalk was stuffed with contraband daily newspapers, I discovered, which made me feel less bad about having run back to my car after getting my assignment, in order to pick up a paperback novel. I had learned about this new book from an advertisement on the chalkboard by the front gate—Killer, by Christopher Newman. The author, in his acknowledgments, thanked First Deputy Superintendent Charles Greiner (now the superintendent of Sing Sing), and as I read on, I saw that Greiner must have given Newman a tour and a lot of background information about facility operations. Killer was about a New York City police lieutenant who was being stalked by a notorious Colombian gunman who had just escaped from Sing Sing.

The scenario was this: The Colombian knew that his best chance of escape would be during an outside medical trip. With his A-block buddies, he created a fake altercation on his way to supper. Shielded from the eyes of COs by milling inmates, he stabbed himself deeply, purposefully creating a sucking chest wound. It worked. He was driven out of Sing Sing through the very gate I sat astride, in an official van that was soon hijacked by his confederates. In the van with the Colombian was a Sing Sing nurse, who was forced to continue treating him.

Greiner, to my surprise, had authorized a book signing for Killer near the lineup room. Any book that postulated an escape, I would have thought, would have been anathema to the superintendent. The fact that it wasn’t gave me heart. Maybe Greiner wouldn’t be so unhappy when my book came out.

UTILITY 1

Occasionally from a wallpost you would see a decrepit Sing Sing van stop somewhere on the road encircling the prison, and out would pile one officer with a chair and five or six inmates with lawn mowers and Weed Eaters. This was Utility 1, a crew of medium-security inmates whose job it was to mow and clean in the area just outside the walls.

One day I had the job of supervising Utility 1, and though it was supposedly a plum, I found it completely nerve-racking: I was terrified that one of these trusted inmates would run off, leaving me to blame for an escape.

This had actually happened recently to Konoval, the training officer, who had taken a different work crew out mowing near a highway in the Bronx. One of the inmates disappeared when Konoval wasn’t looking, only to be recaptured a few hours later at his mother’s apartment in Queens—luckily for Konoval. Those inmates were supposedly even more trustworthy than mine, and Konoval was supposedly a supremely experienced officer. Thinking of him, I actually felt it was likely that it would happen to me.

The inmates and I got into a fight over this anxiety of mine. Apparently, when they mowed the relatively short stretch alongside the south wall of the prison, the regular officer didn’t object if those in the lead went ahead and kept on mowing around the corner. But around the corner was out of sight, and I panicked when they disappeared. Two of them told me they would refuse to work if I made them stay back. “What’s wrong, CO, you scared? We ain’t goin’ nowhere—the towers watch us all the way.”

“Stay in sight,” I said. “If you refuse, I’m writing you up. Or maybe you don’t care about your job.” This was false bravado—I doubt I could have gotten them fired—but it seemed enough to inspire some hatred of me, if not fear.

We had to go back to a storage shed to swap malfunctioning equipment for barely working equipment. To show the inmates I wasn’t a bad guy, I agreed to their request not to take the steep, curvy route that hugged the north side of the facility but to drive a route that was almost as fast, through downtown Ossining. The inmates were mad to see women—any women—and this route was more likely to gratify.

Like several old Hudson River downtowns in the region, from Peekskill to Poughkeepsie, the neighborhood has seen better days. Parts are a ghetto now, with broken-down stoops, prostitutes at night, and guys playing dice against the curb. There was one corner I had always noticed when I passed on previous occasions. It had a large number of fairly well dressed young men hanging around out front, not drinking or gambling, not visibly occupied with anything except paying close attention to passing cars. The inmates waved at them, and they waved back.

“Looks like a crack house,” I commented.

“Of course it’s a crack house,” said the inmate in the passenger seat next to me. “Been there for months.” He seemed to take offense at some condemnation he heard in my tone. “Just guys making a living is all.”

I nodded. (Two hundred feet farther on and around the corner was a ramshackle wooden house directly opposite wallpost 15. This was actually a CO residence inhabited by a changing cast of upstate officers I had worked with; with no knowing reference to the real one, it had been nicknamed the Crack House.) It struck me as peculiar that the crack trade was flourishing openly perhaps a hundred yards from one of the most famous maximum-security prisons in the world.

It had a little bit to do with jurisdictions, I supposed. The Ossining police probably had several crack houses to deal with, and its proximity to Sing Sing did not constitute a reason to go after that one in particular. In fact, the presence of a crack house was not so stunning alongside what I had seen during a day on another plum job, construction.

Officers on construction detail—like the one who had witnessed me getting slugged in the head that day in A-block—accompanied outside tradesmen doing building or maintenance work inside the prison. Once I spent an entire day on top of the Hospital Building, keeping an eye on a crew of roofers who were removing an old surface laden with asbestos and then laying a new one. Essentially, my job was to make sure they didn’t do anything to threaten security, such as drop tools to inmates or leave out dangerous equipment.

During lunch break, I got to talk to a few of them. Like the inmates, they were startled to find that I spoke Spanish. One in particular seemed happy to chat. He hadn’t spoken to any white people apart from bosses since he arrived from Ecuador the year before, he told me. The trip had been a difficult one, and it cost him over seven thousand dollars: He had flown from Quito to Guatemala, then taken a boat to Acapulco. From there he traveled overland to the U.S. border, crossed over to Houston with help from a coyote, and then finally flew on a commercial airline to New York City.

“So you’re still illegal?” I asked.

“Sure,” he said, shrugging and looking at the others resting against the wall, thermoses and lunch bags by their sides, “como todos nosotros.” Like the rest.

Here was a man who had violated federal law—a fugitive, technically—actually working inside Sing Sing. Resting against its very bricks. And not afraid to tell an officer.

TRANSPORTATION

Over four days in my first months on the job, I got to enter another realm normally guarded jealously by senior officers: transportation detail. For people who are in confinement, inmates go a lot of places. They are accompanied outside of prison to court hearings (many, though imprisoned, have additional charges pending), to family funerals, to the hospital, and to other prisons on transfer. Officers on transportation detail get to leave the facility, and because many trips spill over from one shift to another, they rack up lots of overtime pay.

I was sent from lineup one day to work with a transportation officer named Billings. Every trip required at least two officers. If a large contingent of inmates was being moved, even more officers went along. That day, however, Billings and I had only one inmate to transport, a Mexican who had a deportation hearing at an immigration court inside the Downstate Correctional Facility, about an hour’s drive away.

We wore sidearms, and it was instructive to witness the lengths to which the prison went to keep guns—even officers’ guns—out of the facility. First we walked out the prison’s front gate and collected the pistols from the Arsenal’s outside window. Then we drove a state van around the perimeter to Wallpost 18, where I climbed out, my arms laden with the pistols, belts, and holsters. I walked to the base of the tower. “Rapunzel, Rapunzel,” I called, waiting for the tower officer to appear and lower the bucket. He didn’t smile when finally he peered over the railing; COs could be so grim. Then, free of weaponry, we passed through the sally port and went back inside the prison. We placed handcuffs and leg irons on our inmate, helped him into the van, and passed back through the sally port to the outside. Only then, after we had collected our weapons from the wall tower, were we, our guns, and our inmate all finally united inside the van.

The forty-something Billings was an extrovert. He quickly told me about the trouble he was having with his wife due to his extramarital affairs (“I don’t think many men my age haven’t had affairs,” he said) and about the tensions at home due to the return of his pregnant, unmarried teenage daughter. We talked about the union’s new disability insurance program, about the vocational shop at Eastern Correctional Facility where all the state’s highway signs were made, and about an altercation in the B-block yard the night before, during which officers had been injured.

I walked with the inmate into his hearing at Downstate. All morning—from his strip-frisk outside the protective-custody unit to his handcuffing—he had been the soul of civility, and at the hearing he was no different. No, he told the judge, English wasn’t his first language; that would be Nahuatl, the Mexican Indian tongue. But he could understand Spanish well enough. Through an interpreter, the judge explained that the hearing was about whether he wished to fight the government’s plan to deport him to Mexico as soon as his sentence was finished. No, the inmate said, he would be happy to go home as soon as he could. But there was a favor he wanted to ask. He was serving eight to twenty-five years for manslaughter, he said, and for the past three months, he had been held in involuntary protective custody. This was because his victim had been the younger brother of a leader of Sing Sing’s Latin Kings gang and the administration feared that members of the gang in prison would kill him. Couldn’t the judge please intervene and have him transferred?

Conveying all this information to the judge through the interpreter took about ten minutes; the judge’s reply, about ten seconds. “No,” he said. “I’m sorry, but there’s nothing I can do.” And that was that.

Certainly, I supposed, the matter was outside the judge’s jurisdiction. The Department of Correctional Services transferred inmates according to its own obscure agendas. I (probably along with most inmates) was always trying to figure them out—and I made a bit more progress later that night.

My shift was over by the time Billings and I got back. As we checked in, a black sergeant, Brereton, was trying to decide on the racial makeup of a team of evening-shift transportation officers to send on a five-hour drive up to Great Meadow Correctional Facility, the max near Comstock, New York. He didn’t want to send “all brothers” to Comstock—it would conform too much to the upstate stereotype of Sing Sing. But his regular white and Latino officers were out. I raised my hand to volunteer, and was selected. It was overtime, he advised me; I probably wouldn’t get back until 4 A.M. “That’s no problem,” I said. This overtime was easy.

Sergeant Brereton took me and another officer along to collect the inmate from his cell in 5-Building. This was unusual. Normally, transportation officers collected inmates by themselves. When we arrived at the cell, Brereton was fierce to the inmate: “Collect your bag! Put your shoes on! We’re leaving now!” The inmate was a young black guy named Hans Toussaint. He did not seem hostile, but maybe Brereton knew something I didn’t know.

“No talking!” the sergeant barked as Toussaint paused at another cell to say good-bye. “Direct order! Walk in front of us now! Stop again and we’ll take you down!”

Inmates in neighboring cells snickered at this and imitated Brereton in low tones. I braced myself, knowing Brereton would expect me to do the taking down if in fact Toussaint stopped again. Fortunately, he did not, and Brereton dropped us off at the State Shop, where Toussaint’s belongings were to be inventoried before he was shipped out.

A small crowd of six or seven officers gathered around for this routine procedure, and slowly I learned why there was all this interest: Toussaint was one of the gang members who had been involved in the altercation in B-block yard the day before. We had seen videotape of this at lineup: thirty or forty seconds of inmates massing, running and stabbing, attacking and fleeing. The story was that the Latin Kings had a score to settle with the Bloods. Their fighters had gotten to the yard first, armed with shanks, and taken positions along the fence. The Bloods had known a fight was going to happen, known they were outnumbered, but had gone out anyway. They were clustered near the yard door when the Kings attacked, stabbing numerous Bloods and sustaining lesser injuries in the process. As the Bloods fled down a fenced-in corridor toward 5-Building, the video showed Sergeant Murray, his baton out, flailing away to separate the combatants.

I had passed the door where that corridor emptied into the main prison, walked by the large pool of dried blood just inside it. It now seemed likely that some of this blood had been Toussaint’s. He had just transferred into Sing Sing from another prison the day before; it had been his first time ever in the B-block yard. The officers were marveling over that circumstance as they sifted through his meager possessions.

“So you knew something was going to happen out there?”

“Everyone knew it was going to happen,” said Toussaint.

“So why’d you go?”

“I had to go.”

“Where were you stabbed?”

Toussaint lifted up his T-shirt and showed the cut in his back. He would have gotten a “big stick” in his side, too, he said, had it not been for his protective vest of magazines.

“What magazines did you use?” asked Anderson, the female CO who supervised the barbershop downstairs.

“Ebony and Life,” said Toussaint, smiling. He was charismatic, I could see. Officers kept peppering him with questions, but he was talking especially to Anderson. She pointed to three parallel slashes through one of his eyebrows. “What are those?”

He shrugged and wouldn’t answer.

She persisted. “Why the big deal about your gang?” The Bloods, originally from Los Angeles, were a growing and feared presence in New York at the time. It was said that membership followed a strict policy of “blood in, blood out”: You had to slash somebody—not necessarily a rival gang member, just someone you were robbing, say—to get into the gang, and leaving was impossible without getting cut up yourself.

“Okay, I’ll tell you once,” said Toussaint. He borrowed Anderson’s pen and on a piece of scrap paper wrote B-L-O-O-D in block letters. Then he completed the words he said the letters stood for: “Brotherly Love Overrides Oppression and Distraction.” I had never before heard that Blood was an acronym. Anderson folded it up and said she’d keep it.

Toussaint had nothing more to his name than an incomplete set of state-issued clothes and a fat envelope of letters from his girlfriend in Brooklyn. (“Dear Sweetie,” began one, which an officer had opened. “Your bid’s not that long.”) And, like a bunch of idiot nerd scientists, here we were poring over it all with a fine-tooth comb, grinding along to keep the system going—and the gas in our SUVs. By comparison, he was like the Rebel, ideals untarnished. His girlfriend would have to write to him at Great Meadow, now. Instead of being placed in protective custody, like the Mexican, Toussaint was being transferred out. This transfer made sense: Toussaint seemed combustible, and getting him out of Sing Sing would help to defuse gang tensions. I felt suddenly sorry for him. These gangs of ghetto kids preyed on the weak, but you had to admit that there was a political element to some of them, a mission of self-help and a drive to maintain pride and focus. Toussaint was not unlike an ambassador from a small, fierce, and backward land.

The only thing I could say on our behalf was that just as everything was finishing up, an officer happened upon a tiny plastic bag with a few leaves of what looked like marijuana in it, enough for just one puff of smoke. The officer held it up accusingly.

“You gotta have somethin’ when you goin’ out there,” said Toussaint, shrugging.

The officer, instead of writing him up, threw it away without comment.

We pulled into Great Meadow around midnight. The officers we saw were all white, and they already knew about the altercation in the B-block yard. They, too, seemed eager to see what Toussaint looked like. A sergeant gave him a stern lecture and a pat-frisk, telling him to look straight at the wall, keep silent, hands flat … and then offered up a sardonic “Welcome to Great Meadow” when he was done. Actually, Toussaint had told us on the drive up, he’d done time here before.

In return for Toussaint, we received an inmate to take back with us. This game of musical chairs, sort of like a reverse sports draft, was the way of DOCS. Inmates were constantly being shuffled in the hope this would avert volatile situations. You could tell that Great Meadow was tighter than Sing Sing; every time this nervous inmate addressed me, even as I was performing the strip-frisk, he called me sir. The inmate was black. Thinking he had probably grown up in New York City, the same sergeant said to him, “Must feel like you’re going home, huh?”

“No, sir,” said the inmate. “Actually, it doesn’t feel that way at all.”

We stopped on the New York State Thruway for gas, within sight of a number of large tractor-trailer rigs. The inmate had been telling me that the farther north you went in the prison system, the less talking there was between officers and inmates. As we waited to pay for the gas, a big rig pulled out ahead of us, then accelerated onto the entrance ramp.

“That’s what I want to do when my bid’s done,” he murmured, “drive one of those things.”

It made all the sense in the world to me. He wanted to get behind the wheel and eat up the space, drink it in, make his own choices in that great land without walls. He looked like he would have given anything to do it then and there.

One after another, my classmates disappeared. The Department usually gave only two or three days’ notice of a transfer, so often there was no good-bye—just the absence of Dieter, Di Carlo, Colton, Davis, DiPaola, Dimmie, Arno, Charlebois, and the rest, usually to the “jump jails” a short drive north. Occasionally, I’d see a big grin on somebody’s face in the parking lot and they’d show me the paperwork. Bella and Buckner were on their way to Bedford Hills and Taconic, the women’s prisons on the other side of Westchester County. It took a few months, but Miller finally left for the state police academy; Feliciano, for the New York City police academy. A few officers from the city stuck around—Ellerbe, Foster, and Chavez—and I was glad for the familiar faces. I made new friends of more recent OJTs, but reservedly, because they were almost always gone within a few weeks. And I got to know some of the more senior officers better, most of them in B-block, where, shortly, I would be spending a lot of time.

The most dramatic departure was by Officer Mendez, whom I had sat next to against the wall one night at the Academy while waiting for pay phones. Mendez was from up near Buffalo, a strong, articulate, capable-seeming fellow who was still hoping to get into the Secret Service, he told me, and was calling home to see if a letter had come from Washington.

Apparently, Sergeant Holmes had penciled-in Mendez to J-and-N galleries, A-block’s version of R-and-W—a chaotic, transient floor that nobody else wanted. One day, it had proved too much. Assailed by uncooperative inmates, Mendez had finally gone downstairs to the sergeants, screaming, “I can’t do it! I can’t do it!” He wasn’t entirely coherent, and apparently the whole block had grown hushed at the commotion. One sergeant ascertained that an inmate had threatened to punch Mendez in the face and demanded to know who it was. He dragged Mendez back upstairs, but the officer couldn’t single anyone out. “They were all threatening me!” he wailed.

I saw Mendez in the parking lot the next afternoon, after he’d turned in his badge. He had broken down on the phone with his mother that morning while telling her about it, he told a group of us, and she’d started crying too. He was about to drive home.

“Hey, there’s no shame in it,” another recruit said, and the rest of us nodded. But obviously Mendez—who probably would have made a great Secret Service agent—felt like a total failure. I looked at him with sympathy, envy, and—because any of us who remained could be the next one penciled-in by Holmes—fear.