CHAPTER 3

UP THE RIVER

Criminals used to travel to Sing Sing by boat from New York City “up the river” to “the big house,” some thirty miles north. That’s how both phrases entered our language. The prison’s unusual name was borrowed from the Sint Sinck Indians, who once inhabited the site. It may have meant “stone upon stone,” which describes the rocky slope rising from the bank of the Hudson that the prison is built upon.

Once a lonely outpost, Sing Sing now occupies fifty-five acres of prime real estate in suburban Westchester, one of the priciest counties in the United States. The town that grew up around it, once called Sing Sing, is now called Ossining. Up until the 1960s, prison employees could afford to live in and around Ossining, and in many ways they set the tone for life in the area. Now, however, though the town is slightly tattered—Ossining is far from the most desirable address in Westchester—housing prices have pushed out practically all state correction officers. In 1995, the average two-bedroom rental in Ossining cost $1,525 a month, and the average price for a three-bedroom house was $241,000. Away from “the city,” as many recruits think of Westchester County, the same apartment would cost $350 (in Dannemora, New York, near Clinton Correctional Facility) and the three-bedroom house around $64,000 (near Auburn). The department’s “location pay,” meant to help compensate officers assigned to Sing Sing, is considered a joke—about fifteen dollars a week.

In some upstate towns, the prison is the main event, visually speaking: Clinton’s imposing wall runs along Dannemora’s main street. But even though it is huge, a visitor to Ossining will have to look to find Sing Sing. And once there, all she is likely to see is a portion of its immense wall. This main wall, some twenty-four feet high, is punctuated by twenty-one distinctive wall towers but is otherwise as blank as a cop’s face. The longest stretch, atop the hillside, runs roughly parallel to the riverbank, a few hundred feet below; extensions at either end angle down the hillside. No single spot on land offers a good vantage point of the whole facility; you can’t even see the main entrance from the street.

But I wasn’t thinking in these larger terms as I drove “up the river” at dawn on that Monday in late April, my first day at Sing Sing. I was just thinking of the one Sing Sing story I’d heard at the Academy that had really stuck with me. I’d been told it three times, and though details varied, the gist was the same: A trainee from the class ahead of ours, a guy I’d met, had walked up to an inmate smoking a cigarette during his second week in Sing Sing. “There’s no smoking here,” he said. “Better put it out.” The inmate ignored him. He repeated it until the inmate told him to get lost. Then the new CO reached over and took the cigarette from the inmate’s mouth, whereupon the inmate struck him on the head or broke his shoulder bone with the CO’s own baton or punched him in the mouth—the versions varied. He was badly hurt over a cigarette.

The story had stuck because the lesson was vague. Apparently, it wasn’t a good idea to pull a cigarette out of an inmate’s mouth. I suppose I already knew that. But what were you to do in such a situation? Write the inmate a ticket for disobeying a direct order? Walk away and lose face? In how many ways would my authority be challenged inside the prison? And how would I react when it was?

Given wrong directions at the Academy, I parked at one end of the top wall, as far as I could possibly be from the corner of the prison where I was due to report. It took fifteen minutes to hustle down a crumbling cement staircase lined with a rusty railing to the main gate and then down more steps, over the railroad tracks to the flat terrain by the river. Outside the prison walls, just a few feet from the Hudson River, are three low, white buildings that contrast with the rest of Sing Sing in their newness and cheap construction. Two are small prefab bunk rooms for officers and sergeants. The third is the Quality of Working Life building, or QWL, a conference room with sliding glass doors and a wooden deck used for training, meetings, and parties.

Here began the four weeks of on-the-job-training (OJT) that would qualify us to become regular officers (though, technically, we would continue on probation for a full year). I was nervous but excited: Sing Sing, storied and mysterious, was exactly where I wanted to be. And I was glad to be living at home again. For most of my classmates, however, Sing Sing was even farther from home than was Albany. Expecting postings in the lower Hudson Valley, my classmates had begun looking before graduation for cheap, small apartments they could share. Davis, DiPaola, and Charlebois had found one in a bad neighborhood in Newburgh, about an hour north of Sing Sing. Arno, Emminger, Falcone, and some others had found a rooming house—“really, it’s more like a halfway house, with recovering addicts and all,” Arno said—around Beacon. Dieter was staying with Di Carlo and his family. Others moved into the few spaces available at Harlem Valley, a former state mental hospital about forty-five minutes from Sing Sing that was now used to house correction officers. A year before at this former asylum, a drunken CO had shot and killed his girlfriend, also a CO, and a female roommate, over unrequited love. But at twenty dollars a week, the price was right.

We were told to set up enough folding chairs and tables to accommodate the 111 people who remained of our class in four or five long rows. There was a lectern at the front of the room; rest rooms and a kitchen were off to the side. Wearing the same dress-blues uniforms we had graduated in the Friday before, we stood at our tables and snapped to attention when the training lieutenant, Wilkin, entered the room.

Wilkin, a laid-back guy, told us all to take a seat, put our brimmed “bus driver” hats on the table in front of us, and just talk to him for a while. Rumors about Sing Sing abounded at the Academy, he knew. “What have you heard?”

It took a while for anyone to raise a hand.

“That officers here sell drugs,” someone finally ventured.

“Uh-huh,” said Wilkin. “What else?”

“That it’s totally crazy and chaotic,” said someone else. “That inmates run the place, and nobody follows the rules.”

“Mm,” said Wilkin. “What else?”

“That some of the officers are real buddy-buddy with the inmates,” said one of the Antonellis, seeming emboldened. “And that they won’t always cover your back.” It was black officers I’d heard thus disparaged at the Academy, but Antonelli left that out.

Instead of laughing, shaking his head, and denying all this, Wilkin, to my surprise, was circumspect. “No officers, to my knowledge, are selling drugs,” he said. “When they have been in the past and we have learned of that, we have arrested them.

“And inmates don’t run this place—officers do. You will see that with your own eyes on Wednesday.

“And as far as following the rules … we are not an upstate prison. We try to follow them to the letter, and we will expect you to. The new administration is committed to tightening security at this prison. But we are a training facility, and not everything is exactly the way we’d like it to be.”

“Training facility” was not an official designation, the superintendent would later explain; it was just the way things had worked out. New recruits came here to answer the chronic shortage of officers, and they had to be trained. Five thousand had started out at Sing Sing since 1988, sixteen hundred of them in 1996 alone. The department had an unprecedented need for new officers right now, apparently due to higher-than-usual rates of retirement and attrition.

A training officer named Hill told us that our job would be unusually difficult, because “OJTs irritate inmates.” Inmates appreciate a constant set of keepers, he explained; they don’t like having the rules enforced differently every day. Not that it was necessarily a snap being an old-timer, either; one longtime employee had had his nose broken during a scuffle in the yard just the previous weekend. Sing Sing had between 700 and 750 “security employees” at a given time; 34 percent of these officers had less than a year on the job.

We broke for lunch, and afterward, we were each issued a baton. Down the row from me, someone noticed that his had dried blood on it. Next, we lined up to have our pictures taken. First, we faced the camera while holding up a little piece of paper displaying our name and Social Security number and the date, and then we turned for a profile shot—just as if we were inmates being processed at a jail. These were “hostage photos,” one trainer told me, for our permanent files, to be released to the press if something happened to us—such as being taken hostage. I laughed, thinking the man had a dark sense of humor. But he was unsmiling and, I slowly realized, serious. As unsettling to me as the photos’ purpose was the fact that they weren’t called something else—say, employee contingency portraits, or some other euphemism. Calling them hostage photos was like saying we were “guards” in a “prison.”

In the afternoon, we learned more about the inmates. Sing Sing is the second-oldest (after Auburn) and second-largest (after Clinton) prison in the state, and at this time it had 1,813 inmates in the maximum-security prison and 556 in Tappan, the medium-security portion. Of the total—2,369—1,726 were violent felons; 672 had been convicted of murder or manslaughter. In other words, between a quarter and a third of the inmates had killed somebody. Other violent felons had committed rape (93) or sodomy (38) or a variety of crimes including robbery, assault, kidnapping, burglary, and arson. Eighty percent were from the New York City area. Forty-three percent were ages 25 to 34. African Americans made up 56 percent of the inmate population, Hispanics comprised another 32 percent, and whites around 10 percent.

Sing Sing is unusual for a large max in that it has few vocational or other programs for inmates. Inmates are still required to work for their GEDs, but almost all college-level programs ceased in 1994 and 1995, when state and federal lawmakers ended the funding. “Now there isn’t much to take away,” the programs director admitted candidly during his brief presentation after lunch. “We’re pretty much down to the bare minimum. We have trouble finding things for all the inmates to do—there are only programs for three or four hundred men.” The gap was filled with recreation: unstructured time in the yard or gym. Up to sixteen hundred men might be in recreation at a given time.

The superintendent had less than a year on the job, too. Charles Greiner, who was fit, white-haired, and soft-spoken, stood before the lectern and told us he had come up through the system, starting upstate as a CO. We’d been told he was more security-minded than his predecessor (who, old-time officers complained, was overly concerned with housekeeping and appearances) and interested in tightening up the prison. He told us that he had reinstituted assigned seating in the mess halls, so that inmates couldn’t sit wherever they wanted. He had tried to make sure inmates were more securely escorted from cell to mess hall and back. Other reforms were in the offing but would be instituted very slowly, “so as to only create a tiny ripple back.” Situated, as we were, on the bank of a huge river, the metaphor suggested the prison was a big body of water and we were all in it together. Create too big a wave, and we would swamp ourselves.

The atmosphere inside the prison was apparently stressful at present. Five inmates had committed suicide within the past five months. An inmate-grievance system had been instituted after the Attica riot; Sing Sing inmates typically filed about twenty-five grievances a week against the administration, but recently that number had gone as high as seventy-five. Two months ago, the entire facility had been locked down in Code Green emergency status, meaning that an area (B-block) had gone out of control. Still, said the first deputy superintendent for security, Sing Sing was “no more out of control than anywhere else.” Yes, he conceded, there had been “lots of cutting lately.” But, he added, “That’s true everywhere.”

On Tuesday, our second day, we learned more about emergencies. Many of us, depending on our post, would be furnished with radios equipped with special “emergency pins.” In case of attack by an inmate—or any violent situation we could not control—we were to pull the pin out of the top of our radio by tugging on the lanyard. This sent a signal to the arsenal, where an operator would identify the radio’s location and broadcast a special message to all the other radios. The “red dots,” specially designated officers on standby for an emergency, would then run there to offer aid. Other free officers in the area would join them. The response was immediate, we were told, and usually impressive.

If things got so wild that the local red dots couldn’t handle it, red dots from down the hill at Tappan (or up the hill at Sing Sing, if it was Tappan that had the emergency) would be summoned. If they couldn’t control things either, the Code Green would be called and supervisors were to send all available officers to the trouble spot. A milder state of emergency, Code Blue, called for ceasing all inmate movement and locking down the whole jail. A Code Blue would be called if, for example, the count came up an inmate short and finding him was the top priority. No officers would be allowed to leave the building; wall-tower officers were to step out onto their catwalks with rifles in hand. Everything would be frozen until it was certain that no one had escaped.

Later that day, we were shown a movie produced by the Department, called Games Inmates Play. The film, starring state COs, was a primer on how not to let inmates manipulate you for their own ends and make a fool or a criminal out of you. It dramatized three situations that, we were told, had actually occurred in the past two years. In one, an inmate “porter” (trusty, in more common parlance) sweeping the floor around the officer’s desk became privy to his football pool and collected evidence from his wastebasket; when the CO wouldn’t help the porter set up his own pool, the porter threatened to turn him in to his supervisors; the CO did the right thing and fessed up to his sergeant and lieutenant. A second CO didn’t come clean soon enough, though. After working near one congenial-seeming inmate for a long time, he’d become so comfortable talking to him that he’d confided to the inmate about some problems at home and a shortness of cash. The inmate offered to help him out by paying him a hundred dollars just to bring in a package from his brother. After hemming and hawing for a while (inmates are forbidden to possess cash, which is almost always connected to drug traffic), the officer finally agreed. The final scene of the vignette showed him pulling into his driveway that night and being arrested in front of his disbelieving wife and kids.

Finally, there was the tale of the civilian teacher who allowed an eager inmate to help her grade papers and confided in him when her boyfriend dumped her. He asked if he could take her out when he was paroled in six months. Yes, she indicated, but then he told her he couldn’t wait; they were caught by an officer having sex in a storeroom, and she was fired.

The moral was: Don’t confide in an inmate about your personal life. And don’t be tempted by bribery or other offers. The moment an inmate gets anything on you, he’ll have power over you and is certain, eventually, to sell you out.

After all these warnings, a training officer finished our second day with one more. “By the way,” he said, “we’ve had a problem lately with brown recluse spiders in the facility.” Three COs had been bitten by the venomous spiders, he said; one officer got so sick that he required chemotherapy. “So just make sure to shake out your jackets if they’ve been hanging up, or look around a desk before you sit down.”

Spiders—on top of everything else.

It had been driving me crazy to be right next to Sing Sing but unable to go inside. On Wednesday that changed.

As our tour group walked the perimeter fence to the main gate, I noticed that we looked slightly different. No longer was everyone so obsessively concerned with his uniform. Sing Sing, it was clear from watching the training officers, did not care much about the polish on your shoes or the crease in your shirt or the length of your hair. Instead of everyone wearing the long-sleeved gray shirts prescribed by the Academy, some had slipped into the short-sleeved version, despite the still-cool spring weather. Other officers now spurned their black oxfords for more casual boots, especially the lightweight Bates and Hi-Tec brands, which were popular among police. And our belts, newly laden with batons, had begun to spring key clips and latex-glove holders, though no one had told us to put them on yet. A new groove had been set, and officers were sliding into it.

We passed through the front gate and several more as we made our way up the hill. Our group felt very white to me compared to the on-duty officers we passed—and particularly compared to the inmates we saw. But the real revelation came in one tight corridor when our group passed an inmate group of nearly equivalent size. As we tried to squeeze into half the hallway, arms and shoulders didn’t just brush, they rubbed. This wasn’t like the small group of subservient workers we’d known at the Academy or the double-file inmates from the roomier halls of Coxsackie. This was something with mass and energy, something … unnerving. I was thinking how easy it would be for someone with a knife to do some damage to us—and get away with it. Ahead of me, one of the Antonelli brothers suddenly turned around and gestured to us, trying to subtly point out one of the inmates—a transsexual, complete with breasts: nothing you wouldn’t see on any given day in Greenwich Village or on the city subways, but decidedly exotic if you were from rural New York. Bella and Chavez seemed more at home with the mix. As we turned the corner, Bella commented, with some satisfaction, “It’s just like the city!”

Ahead of us, a Plexiglas sign hanging from the ceiling announced HOUSING UNIT A. Underneath, there was a barred gate with a solid-metal door behind it. Our guide pushed a doorbell and we heard ringing on the other side. Finally, an officer inside pulled open the door to admit us to A-block and our first glimpse of the great cavern, so drab and yet so stunning. We stood slack-jawed, trying to make sense of the railings, the fences, the bars, and the spaces, both tiny and immense. Our training officer commented on the fame of the building, how corrections officials from around the world came to visit it. It was hard to hear him, due to the din. Heavy gates were being slammed; shouts echoed. We moved closer. When he stopped talking, we followed him up the center stairs and walked a long gallery or two, attracting a couple of epithets—someone called out, “Clarence Thomas!” to Dimmie (meaning Uncle Tom), and we heard a few cries of “Newjack!” But it was nothing like our experience at Coxsackie: Even these hardened inmates, who so outnumbered us, were intimidated by a large detachment of officers.

A-block had a big gym but no adjacent yard. In another quirk of Sing Sing, the yard was way down the hill and across the tracks, next to Tappan. Before heading that way, we visited 7-Building, the “honor block,” with space for eighty-six inmates who had gone several years without being cited for disciplinary infractions. And then we went to 7-Building’s opposite, the Special Housing Unit, a two-story structure that housed sixty inmates; it was larger and grimmer than the one at Coxsackie. While 7-Building’s yard contained a running path, benches, vegetable gardens, and a great view of the Hudson River, the SHU had a bare blacktop courtyard divided in two by a chain-link fence. Down a dogleg corridor from the SHU was the State Shop, where inmates on their way in or out of the prison were processed and given clothes and bedding. On the first floor of the State Shop building were a fourteen-chair barbershop and a shower room (rows of individual stalls without curtains, and lookout points for supervising officers).

On the way to B-block we passed 5-Building, a small cellblock (housing 272 inmates) with floors devoted to distinct groups: recent arrivals to Sing Sing, including transfers and absconders (former inmates captured after parole violations); mess-hall workers; and inmates with mental health problems. We saw the laundry, one of the few freestanding buildings in the maximum-security section, and the mess hall, with its busy nexus—“Times Square”—which sat right in the middle of the dining rooms for A-block, B-block, and 5-Building. The chapel building, opposite B-block, was used mainly to show movies, but it had churchlike worship spaces for Catholics and Protestants and areas in its basement for Muslims, Jews, and Quakers.

Sing Sing’s maze of corridors, gates, and staircases had grown organically over the years according to the demands of the particular era; no master plan had guided the development. Looking out from some high windows, you could see a dozen red-brick walls facing different directions and the roofs of the many connecting corridors. Some of the beautiful slate shingles of these roofs were missing, and decaying soffits hung down from them, too. There seemed to be a score of little courtyards, half of them abandoned and overgrown. The whole area was dotted with small sheds, and the buildings themselves had a mishmash of additions. The gyms of A-block and B-block, for example, had been oddly appended years after the original construction. The interior of most corridors was painted brick and cinder block. No one could memorize this layout in a day—perhaps not even in a week—and yet we weren’t allowed to bring our maps inside; they were thought to be a security risk. Still, we didn’t need them to wonder what had happened to 6-Building or 3-Building or 4-building, the gaps in the number sequence, buildings perhaps constructed but then abandoned or renamed.

The most startling corridor—my favorite, actually—was the long, semi-open one connecting the max facility to the school building and Tappan, across the railroad tracks. The walls of this corridor were a series of barred arches, through which rain and icy winds blew in bad weather. With its peeling, chipped paint and water stains, the interior had the air of a colonial ruin. Past the school gate, the corridor was fully enclosed and, for reasons I still do not understand, partially unlit. At one staircase, if it was bright outside, the contrast with the gloomy tunnel dazzled you so much that it was hard to see the steps; you had to feel your way down with your toes. Set into the wall by these stairs was an old, rusted gate, and an inmate would later ask me if that was where the Death House used to be. Certainly it looked like it.

But it wasn’t. The Death House, 15-Building, was an old brick structure down by the river. It had been converted, following the abolition of the death penalty in New York State, to a vocational building with modest print, drafting, woodworking, welding, and small-engine shops. Old Sparky, the electric chair, had been removed to a museum in Virginia; Death Row, converted into an orientation classroom. Six hundred and fourteen people (including Julius and Ethel Rosenberg, convicted of selling atomic-bomb secrets to the Russians) had been executed here, but there were no plaques; the only links to the past were the memories of officers like the one who showed us where the chair had been, and the switch, and the so-called Dance Hall—I thought I recognized it from a James Cagney movie—through which condemned inmates passed on their way to the chair.

Tappan had a much different feel from the Sing Sing max. Its three-story cinder-block buildings had large, open dorm rooms, containing up to seventy-five inmates each. The dorms were divided by waist-high partitions into single or double cubicles. There was freedom of movement within the dorms except during the three daily counts; inmates washed their own clothes and could cook their own meals, and there were television rooms. A single officer sat near the entrance to each room at a large desk, and it was a sought-after job, for though some of the inmates had committed crimes of the same violence as inmates “up the hill,” they were in the last five years of their sentences, tended to be older, and were often on track for parole. Tappan had its violent incidents, but much less often than the max facility.

Outside the three dorm buildings was a large gym, built by Warner Bros. as thanks for use of the Death House and other prison sites in its gangster movies of the 1930s. And outside the gym were a weight-lifting area and a lawn, tended by inmates who, on warm days, reclined there.

We’d been up the hill and had come back down. Before we climbed back up to the main gate, we were given a closer glimpse of the fence that substituted for a wall along the riverfront and on either side of the sunken railway corridor. It was a double fence, actually—two high chain-link barriers topped with spirals of gleaming razor ribbon and a kind of no-man’s-land in the eight or nine feet of ground between them. In this zone, infrared sensors checked for movement, with strands of taut wire and electromagnetic green wire providing redundant protection. It was the sort of thing squirrels and birds could wreak havoc on, our guide said, which was one reason for the system of zoomable, rotatable cameras mounted along the top, which were monitored in the arsenal. The entire system had cost about $12 million, he said. As we showed our I.D.s to leave the prison—a safeguard against inmates walking out the front door—I decided that if I were an escaping inmate, I’d stay away from the fence.

As we walked back to the QWL building, we spoke among ourselves of how run-down Sing Sing was. But in the debriefing by Lieutenant Wilkin, the focus was on how chaotic it was, how so many of the rules weren’t respected. Several times, by now, we had been quizzed by the training staff on the contents of the Inmate Guidelines booklet. There were ninety-nine guidelines, all of which we had to memorize, governing the minutiae of inmate life. For example:

31. You will be allowed to carry a maximum of two (2) packs of cigarettes on your person. Only a maximum of six (6) cartons of cigarettes will be allowed to be stored in cells/cubes. [An inmate in possession of more than this was likely a “mule,” collecting or paying off some illicit debt.]

36. Visibility into the cell … must not be obstructed by … furniture, clotheslines, clothes, bedding, or towels.

24. Pictures, photographs, newspaper clippings, and one small national flag (10″ × 12″) … are to be … taped or fastened at the top only on the cell wall in the [designated] 2′ × 4′ area. Other symbols not authorized will be confiscated.

25. Display of pictures or photographs of nudes will only be placed where they cannot be seen from outside the cell or cubicle (above cell door, or inside locker).

Metal hangers weren’t allowed. Music could be played only through headphones, not speakers. Beds had to be made before inmates left their cells.

But we told the lieutenant we’d seen many of the rules broken: sheets hanging from the bars, hard-porn girlie shots staring us in the face, music blaring from radios, a dozen cigarette cartons lurking under a table. What was the deal?

The lieutenant gave a little smile. “As I said, this is a training facility. Not everything is exactly as it should be. We’ll need your help to make it that way. In fact, we’ll demand it: Your job is to enforce the rules.” The lieutenant was a man stuck in that kind of bureaucratic crack where you have to pay lip service to the way things should be yet at the same time acknowledge the reality or appear to be an out-of-touch fool. I just wondered if they were really planning to make us enforce the rules when nobody else did.

One of the female officers then asked an eminently sensible question: “But are we supposed to talk to them?”

The lieutenant didn’t get the question. He apparently didn’t know that in the Academy, we had been ordered not to talk to the inmates around us. But the idea of not talking to them here was so preposterous to him that he had a hard time grasping the concept.

“Of course you have to talk to them!” he finally said. “You’d better talk to them. How else are you going to let them know what to do and hear what they need from you? Oh, yes! The job is all about talking to them. That’s really what it’s about.”

That echoed what Sergeant Bloom, head of the Academy, had told us. And yet it seemed to be a point of pride among Bloom’s instructors that the training was about us, not about them. We’d been taught that worrying about inmates’ concerns was tantamount to pandering, that it almost demeaned an officer. Let them worry about how to communicate with us was the more common attitude.

As we walked out to the cars, the Antonelli brothers were muttering that others might not enforce the rules (the wimps!), but they sure as hell were going to. We passed under one of the watch-towers along the river, and someone noticed a familiar face—a recruit from the class ahead of ours, the guy who had taught us to short-sheet our beds.

“Hey, how’d you get that job?” someone asked him as we all craned our necks skyward.

“I think it’s because I was the high scorer on the range in my section,” the man answered. (I’d later learn that this was highly unlikely; Sergeant Holmes was oblivious of our scores.)

We told him how chaotic it seemed to us inside the prison. “Any trouble getting them to do what you say?” asked a recruit.

“I just swear at ’em,” he replied. “It’s the fastest way to get the job done.”

The following Monday morning, we began training inside the prison. I threaded my baton through its ring on my belt, trying to imagine a scenario in which I might have to wield it. Before joining regular officers in the lineup room, our group had a separate lineup at which we received our assignments. Mine was the floor of B-block containing galleries R and W, and I was to assist the officer on duty there.

On our long hike up the stairs, minutes behind the regular officers, few of us had anything to say. We trainees were strangers here. Our heads were filled with rules and anecdotes, but we lacked any real knowledge of how to perform the job that was ours as of today. Now separated, we would each face our fear alone. Our main problem, it seemed to me, was that the state had certified us as lion tamers before ever leaving us alone in a cage with a lion.

Our group got smaller the farther into the prison we went, with groups breaking off at the hospital building and at every side corridor. One particularly large contingent exited at A-block. The dozen of us remaining strode off down the dark hallway to B-block, listening to the sound of our shoes hitting the concrete floor.

Like A-block, its fraternal twin, B-block was a massive structure. We clustered near the gate like a small herd of doomed sheep, looking at the galleries above. Inmates who were out of their cells on the galleries gazed back down on us. OJTs, we heard ourselves called again and again, and newjacks. Officers around us were smoking, though nobody was supposed to. We heard gates slamming, music playing, men yelling, and showers running as though B-block were one immense locker room.

We stood on the flats, ground-floor corridors that encircle the tiers of cells. The cells are arranged with two galleries, or rows, back to back on each tier. From top to ground level, they are:

U and Z
T and Y
S and X
R and W
Q and V

The Q-and-V galleries are on the flats. The Q-R-S-T-U galleries comprise the “front side,” or river side, of B-block; V-W-X-Y-Z, the back. B-block’s letters were what was left of the alphabet after the galleries had been named in 5-Building (A, B, C, D), 7-Building (E, F, G), and A-block (H, J, K, L, M, N, O, P). The anonymity of it all was telling, I thought. Every other public building in the country was eagerly associated with the glory of a leader or, in recent years, a corporation: the John F. Kennedy Center in Washington, D.C., the Alfred Murrah Federal Building in Oklahoma City, Houston’s Hobby Airport, 3Com Park, Coors Field. But there was no Microsoft Men’s Correctional Facility, say, and no Reagan Center for Juvenile Detention. Prisons were usually named after places; their buildings, after letters of the alphabet.

The officer in charge (OIC) appeared, warned us not to let out any keeplocks, and then ordered us up the center staircase to our assignments. To get to the top, we had to pass through a locked staircase gate on every single floor. R-and-W was just one floor up, but it took a long time to get there. “R-and-W, center gate!” we yelled again and again. Through the mesh we could see a lot of inmates milling around, apparently arriving on the gallery via some other entrance. Finally, a gray uniform appeared among them, and an officer in his early thirties plodded up, stuck a key in the gate, and pulled it aside. We passed through, my fellow trainees quickly disappearing up the next staircase. I held out my hand. “Conover,” I said. “Here to help you today.”

“Okay, here’s your keys,” said the officer, passing to me two of the four heavy rings on his belt. His name tag identified him as Fay. “And here’s the keeplocks.” He dug in his shirt pocket for a scrap of paper with the numbers of a dozen cells on R and as many more on W. As I began to copy them down, he said of the regular inmates, “They’re just coming back from chow.”

Around us was pandemonium. Inmates were crossing from the R side to the W side and back again through the center passage, which I had a feeling they weren’t supposed to do. Fay, instead of trying to impose order, appeared distracted by the succession of inmates presenting him with special requests. One wanted him to make a phone call; one wanted a form; one wanted a new bed. Fay was tall, round-shouldered, and bald, and wore a baseball cap with a state corrections emblem. He looked like he could be a deacon in a conservative black church. He himself had finished his training just a few weeks before, he would tell me later in the day, and did not have much experience on the galleries. He was, I would ascertain, not especially smart, and his slow wits and mild manner were no match for the chaos swirling around him. I watched helplessly, awaiting further direction.

“What do we do now?” I finally asked.

“Get them into their cells,” said Fay.

“And how do we do that?”

“You just tell ’em,” said Fay. “Why don’t you take that side”—he gestured to W gallery—“and I’ll take this.” I took about five steps and looked both ways down W. It was 425 feet long and three and a half feet wide. At the exact center of it was the staircase, where I stood. The view to either side was of a sort of tunnel with cells defining one wall and a mesh fence overlooking the flats the other. Of the sixty-some inmates who lived on the gallery, fifty must have been out of their cells. The narrow space outside the cells was stuffed with inmates. Many of them were engaged in shouted conversation with inmates down on the flats. Maybe seven out of ten were black, another two Latino, and the last one white. The greatest number seemed to be young, well muscled, and in their twenties.

On our tour and during the twenty-five minutes or so I’d been in B-block, I’d heard officers yelling a line that seemed appropriate to a situation like this, so I started: “Gentlemen, step in, please! Step into your cells.”

Most ignored me, or seemed to. But I persisted, and in five minutes maybe half the inmates had disappeared from the gallery, presumably into their cells. I made my way from one end to the other, saying “Excuse me” to inmates in the way, and repeated my mantra. “Step in, guys—time to step in.” One of them imitated me but then smiled when I stared at him. I began to grow irritated at a handful who continued to ignore me; at an upstate prison, I knew, this would never be tolerated. I decided to make it personal with one, who I felt was making a show out of ignoring me.

“Time to step in, pal. Five minutes ago.”

“Pal? You’re not my friend.”

“Step in anyway. It’s time.”

“Time for you, maybe, not time for me.”

“No?” I said, on the verge of anger.

Suddenly he grinned. “Chapel porter, CO. I was just leaving.”

“Chapel porter?”

“Yeah, I go every morning. The regular officer knows. Or you can call Officer Martinez over in the chapel.”

“Maybe I will,” I said, jotting down the name.

He’d either bamboozled me or had a little fun, neither of which was the outcome I’d hoped for. I had just decided to approach the next guy who was still out when an inmate called to me from his cell.

“CO! CO! They didn’t call me down for my medication.”

“Yeah? What are you supposed to get?”

I waited half a minute while the man doubled over with a deep chest cough. He started to speak again, then coughed in my face.

“TB pills, man, gotta take my TB pills every day.”

I wiped my face. He didn’t seem to have coughed on me intentionally; he was just heedless. “What’s your name and cell number?”

He told me his name and then pointed out the cell number painted by the door lock. “You’re new here, right, CO?”

“How can you tell?” I said ruefully.

“You know who you look like? You look like that guy on Three’s Company, CO. Know who I mean?”

I nodded.

“Anybody ever tell you that?”

“No,” I said. “I’ll get back to you.”

I went to ask Fay about the chapel porter and the medication when I realized, through the din, that somebody had been shouting “R and W, center gate!” a number of times and that I probably had the key. I fumbled with my rings, tried a likely candidate, and was pulling open the gate when I realized it was inmates on the other side—about four of them—not officers. I hesitated, and stopped with the gate open two or three inches.

“What are you going down for?” I asked.

“OIC porters, CO, come on!”

“I’ve never heard of OIC porters,” I said—which, I would learn, was a mistake. You were never supposed to betray your ignorance to inmates.

“Oh come on, man, you’re new. We do it every morning.”

Without closing the gate, I told them to wait. I’d check it out. I threaded my way down R-gallery, which seemed to have even more inmates on it than W, and finally found Fay, who said to let them through and to call the hospital about the TB pills. But when I returned, the gate was wide open and they’d let themselves through—a significant offense, I thought. Certainly it was one of the ninety-nine rules—inmates were never to touch gates, apart from the doors of their own cells. Or was it my fault for leaving the gate open? I was debating whether to follow up on this when I heard the phone ringing inside the cell used by R-and-W officers as an office. I signaled to Fay over the heads of several inmates, and he indicated I should answer it. Finding the right key took about twenty rings, and at first there was no one on the other end of the line. Then a voice demanded to know why we hadn’t responded to the page over the public address system. The inmate in W-21 had a visit. I hadn’t even heard the page, I confessed. The OIC sounded exasperated. “Are your galleries clear yet?” she demanded. “No, not quite,” I said. “Well, clear ’em up now!” she ordered, and slammed down the phone.

I went to ask Fay what to do about the visit, and he told me to let the guy out. Since I’d never succeeded in locking everybody in anyway, that would be easy, I thought. I went and told the inmate he could go. “I know that,” he said. “But now what about my shower?”

“What about it?”

“You gonna let me into the shower?”

“It depends. Why should you get a shower?”

The inmate’s impatience reminded me of the OIC’s. He sighed as though trying to keep his blood pressure under control. “When you get a visit, you automatically get a shower,” he said in a patronizing tone. Fucking newjack.

I let him into the shower, allowed two officers and an inmate through the center gate, and then returned to the task of trying to clear W-gallery. Every inmate still out claimed he was a porter—an inmate employee who swept, mopped, or cleaned up the common areas at a designated time. There were maybe seven of them. I couldn’t imagine that we needed more than two. I went to ask Fay, who said there should be a list posted somewhere.

“Like where?”

“In the office somewhere, maybe.”

I walked back to the office. The phone was already ringing. A lieutenant wanted me to check the logbook for an entry written three weeks earlier, something about when an inmate had been keeplocked. The logbook was a maroon tome that the first officer—Fay—was supposed to keep current all during the shift, noting who the keeplocks were, what time chow was called, when inmates returned from chow, who went out on a visit, and so forth. Fay hadn’t written a line since signing in an hour and a half ago. I turned back to try to help out the lieutenant, but the handwriting on the day in question was illegible. I apologized, but it was no comfort to the lieutenant, who slammed down the phone. I resumed my search for the porter list. What I found seemed ancient, but I copied down the cell numbers for A.M. porters anyway and returned to W-gallery.

An inmate was standing outside the shower cell I had unlocked for the inmate who had a visit. He was wearing only a towel. “Why are you here?” I asked.

“Gym porter, CO. I can’t take my shower in the afternoon, so I get it now.”

“Says who?”

“The regular officer—he always lets me do it.”

“But you haven’t done any work yet.”

“And I won’t do any work, either, unless I get my shower. You can call over there, CO. Ask for Officer Ebron.”

I decided I would do just that, but then I remembered the more pressing matter of inmates still outside their cells who were claiming to be porters. In the next ten minutes, I managed to anger or amuse most of them, or so it seemed, by trying to enforce my hopelessly outdated porter list. Then I heard new calls to open the center gate. “Sanitation porters,” said three Latino men with plastic garbage bags in their hands. I let them through.

“Who the hell gets to go through the center gate?” I demanded of Fay when I saw him, my stress making itself plain.

“Only those who are authorized,” he answered.

“And who’s authorized?”

“Well, you know, officers, certain porters, inmates on a visit …” His voice trailed off as he reached the limit of his knowledge.

It was barely two hours into the shift, and already I felt I was near the end of my rope. Fay and I weren’t coming close to making the inmates do what they were supposed to do, and I was uncertain about whether I should use my power to compel them. Refusal to “lock in” was considered a petty offense. Tickets, officially known as Inmate Misbehavior Reports, were the means by which we had an inmate keeplocked: After locking him into his cell, we filled out a form, got a sergeant to sign it, and sent it off to the Adjustment Committee. The inmate, once “written up,” faced three or four days of constant confinement until his hearing, and then possibly weeks or months more if the Adjustment Committee agreed that he was guilty. Apparently, there was a way around the paperwork for a petty offense. If I understood the talk, an officer could “mistakenly” deadlock the cell of an intransigent inmate just long enough to make him miss his morning or afternoon recreation. But I wasn’t prepared to try that on my first day.

Before my despair could deepen, the OIC started calling the program runs over the PA system—chapel run, school run, commissary run, State Shop run. Since my inmates would soon be leaving, there was no longer any point in trying to clear the galleries, which was both a humiliation and a relief. At this moment Konoval, one of our training officers, showed up and asked how it was going. “Could be better,” I confessed.

Blithely unaware of how bad things really were, Konoval led me down the gallery and asked, “How about the cell compliance?” This referred to the rules about how inmates kept their cells—making their beds, not placing objects on the bars, porn on the wall, fabric over their light fixtures, etc. It was the last thing I was worried about, but Konoval strode purposefully ahead, grunting his displeasure at the number of sheets inmates had hung up, the music being played through speakers, even the smell of cooked garlic coming from one cell. (Inmates weren’t allowed to cook.)

“118.21, fire hazard,” he said balefully, pointing out a pile of papers. We moved down the line. “118.30, cleanliness and orderliness. Write these cell numbers in your notebook.”

We passed over to Fay’s side. A few cells down, to my amazement, a young Latino inmate was out on the gallery cutting an older man’s hair with electric clippers. The old man was sitting on an upended box; on one side of his head, the hair was quite short; on the other, still shaggy.

“No, no, no,” said Konoval. “A haircut on the gallery? Pack it up.”

“But, CO!” protested the young barber. “I just need a couple more minutes!”

“Sorry. Now.”

“You gonna make him stop when he’s only halfway through?” the old man asked Konoval.

“That’s right.”

The men grudgingly complied. I was relieved to see an officer command a modicum of respect and wanted Konoval to stick around, despite his tsking over housekeeping. But he had other galleries to check. I let him into the office to sign the logbook—he expressed shock at the lack of entries—and then let him out through the center gate. I turned to wend my way through the large number of inmates responding to the announcements for gym and yard runs—I hadn’t even heard them—when a tall, lanky black inmate in a muscle shirt yelled, “Hey, CO!” As I turned to face him, the short, bulky man at his side went through nine tenths of the motion of landing an uppercut on my chin. He stopped maybe an inch away, and as I jumped reflexively backward, the two of them dissolved into laughter and strolled off down the gallery. 102.10, I thought, threats to an officer. But was it a threat if they were only kidding, if they were just trying to make a fool out of me? I tried to calm my pounding heart and wondered if I should have pulled out my baton. I wondered how I’d last five more hours.

They placed us on different shifts for the next three weeks, and every day I was at a different post—thank God. The idea was that the regular officer at each post would teach us what he or she knew. But even if the regular officers were there (and not on their day off), in practice they were often sick of constantly explaining things to OJTs and tended to ignore us.

This was the case later that first week, when I was assigned to the State Shop along with DiPaola, Davis, and Colton. Apparently, some days in the State Shop were busy—the shop provided blue jeans and button-down shirts to inmates with court dates and inventoried the belongings of inmates on transfers—but this was not one of them. Still reeling from my experience on the gallery, I was mainly relieved to have some downtime, but the others were on edge and found the lack of activity excruciating. We stood around waiting while the regular officers took all available chairs in the tiny dayroom and drank coffee. Finally, a senior officer instructed us to do a Fire and Safety Report—a daily form for which you count and check the readiness of an area’s fire extinguishers, fire-alarm pulls, emergency lights, etc. We discovered that the faucet handle for a fire hose was missing—you wouldn’t be able to turn it on in a fire—and duly noted it on the form. “Oh, I’ve got that in a drawer somewhere over here,” the officer said when he read it. “It’s to keep any inmates from turning it on. They did that once. Hey, don’t worry about it. Write up a new form.”

“Without mentioning it?”

“Right.”

I pictured Sergeant Bloom, red in the face, saying accusingly, “False report!” We might be held liable if the State Shop burned down! But we rewrote it, because we didn’t want the officer to hate us. Reality had set in.

Three more hours passed with nothing to do. DiPaola finally said, “I didn’t think prison work was going to be anything like this. I don’t want to just stand around and play with my fuckin’ dick all day.” Another hour passed. It was now Friday afternoon. Three newly arrived inmates were placed in a holding cell near us, awaiting their issue of clothing, and one started watching Davis.

“Be drivin’ home up north to visit the missus this afternoon, right, Davis? Countin’ the minutes?”

Davis ignored him. But it was unnerving. Inmates had little to do but watch the officers, we’d been told in the Academy; “you’re like their TV.” From careful watching, they’d read his name tag; from Davis’s wedding band, they knew he was married. From our behavior and the way other officers talked to us, they knew we were OJTs (and therefore that we had the weekend off). Statistical probability told them that Davis was from upstate; maybe something in his bearing betrayed it, as well.

Finally, four inmates arrived who had to be strip-frisked before being placed in a holding cell. This was Nuts and Butts, in officer parlance, a very specific procedure that had to be followed to the letter. (Blurred, laminated photocopies of some court order regarding this search were posted in bathrooms; apparently, inmates had won some redress in court because officers had conducted the searches disrespectfully.) We’d quickly been taught the procedure at the Academy, but Davis had spent the entire previous day doing strip-frisks outside the Visit Room: All inmates had to submit to one after a visit, to make sure they hadn’t been passed any contraband (primarily cash or drugs) by a visitor. So Davis went over it with us.

My inmate, Ortiz, was clean-shaven, slope-shouldered, bespectacled, and out of shape; he looked like a college student. He handed me cigarettes and matches from his pockets before entering a small cubicle with a curtain for a door. Then he passed me out his glasses and clothing as he removed them: T-shirt, trousers, socks, shoes. I ran my fingers over each item, hung them all on pegs, and stepped inside.

He stood naked facing me on a small square of carpet, briefs in his hand. He offered them to me, and I checked them quickly. There was some blood in the seat. “You okay?” I asked. He nodded, and I began directing him through the obligatory motions. But he knew them better than I did and was always a step ahead.

“Hands through your hair. Pull your ears forward. Mouth open. Put out your tongue, pull out your lips and cheeks.” I looked quickly under the tongue. “Arms up.” I checked the armpits. “Turn around.” He did, and immediately bent over and spread his buttocks so I could see his anus. “Fine, thanks.”

I left the booth so he could dress. That was my first strip-frisk, and I hated it. I hated Ortiz’s pliant submission. I almost wished he had resisted more, caused me some trouble—I didn’t enjoy his servility. I didn’t enjoy the visual memory of his anus and dick and the blood on his underwear. (“’Roids,” DiPaola would suggest later.) Half an hour before we left, an inmate who was being transferred to another facility (on a draft, in the lingo) came in with his personal property to be inventoried. His state-issued clothing was all clean and immaculately folded: six T-shirts, three pairs of green trousers, three green short-sleeved work shirts, one white dress shirt, one green sweatshirt, one zippered winter coat, six sets of underwear, “Felony Flyer” sneakers, and leather half-height boots. He had a Koran and a couple of spare kufis (skullcaps). It took us all of five minutes.

“Enjoying yourselves?” asked a black officer who I assumed was an old-timer. He’d been out of the Academy only a few months, it turned out, but had already been assigned several times to the State Shop. His take on the boredom was that it “beats working a gallery.” But a given day could bring either one—hair-pulling overwork on a gallery or absolutely nothing to do in a place like the State Shop. I thought of myself as a fairly flexible person, but not knowing what each day would bring was nerve-racking. What were you supposed to do—shut down your brain when you walked into the prison or drink extra coffee and prepare to go into overdrive?

“I just try to make myself go numb,” he said.

Ten days later, after I’d spent some time in A-block, Davis, DiPaola and I worked together again, this time in B-block. DiPaola was on the U-and-Z galleries, at the very top, and Davis on S-and-X, in the middle. My job, by comparison, was humdrum: I was posted at the front gate, the main passage into and out of B-block. Several times an hour, when I heard the doorbell ring, I’d stick a key into the heavy metal door, twist it, and give the door a big shove to let an officer or inmate with a pass in or out. It didn’t close easily; you had to open it wide and then use its momentum to swing it shut. In an emergency, I was supposed to step outside the block into the corridor and lock the door from there. That way, any disturbance that got out of hand could be contained.

But the job was so dull that I was almost dozing off and could hardly respond when the radio of a nearby officer loudly blared out the emergency tone. An alarm had been pulled on S-and-X galleries, a voice advised. All red dots were to respond.

Half a dozen officers rushed upstairs through the center gate. Shaking myself into wakefulness, I let another half-dozen red dots in through the front gate before stepping out, locking it, and leaving B-block to its fate.

Ten minutes later, the emergency was over and I went back in. The red-dot officers were coming down the stairs with two inmates in handcuffs. One had a deep cut across his face and was bleeding profusely. He was taken to the Sing Sing emergency room. The other, who had attacked him, was locked into an empty shower cell. Apparently, an officer on U-and-Z had mistakenly unlocked a keeplock’s cell. Taking advantage of this error to settle a grudge, the keeplock had walked out of his cell when the brakes were opened to let inmates go to their programs, descended two floors to S-and-X, burst into the cell of his unsuspecting enemy, and slashed him.

Fifteen or twenty minutes later, sergeants were interviewing Di-Paola and Davis—they had been working on those same galleries—as well as other officers who had been involved. Within an hour, rumors were circulating among our class that DiPaola had been the one who let the inmate out. He denied it, and of course, there was no way to know for sure. Keys were passed back and forth between officers all the time. Still, regular officers reflexively blamed OJTs when there was a screwup, and often they were right. Before our shift the next day, the training officer underscored the seriousness of what had happened and said that the injured inmate was very likely to sue the Department. A lieutenant entered the room just as this comment was being made.

“I don’t give a shit about the inmate,” he said, unexpectedly. “An officer could’ve been cut. Who here could live with that?” We were quiet. I don’t think anybody had expected the case to turn into a lesson about protecting our fellow officers.

Keys were power. And they were responsibility—because many, many bunglings could be traced back to a set of keys and the person who had been entrusted with them. When to lock and when to unlock was, by one reckoning, what we were here to learn. “You are never wrong, in prison, to lock a gate,” a sergeant had reassured us at lineup one day. But it was more complicated than that. Gates had to be unlocked for the prison to function smoothly—and then, at the right moment, to be locked again. Sing Sing was a place of, probably, over two thousand locks, many with the same key. The cardinal sin, the one thing you were never, ever to do, was lose your keys. A lost key could fall into inmates’ hands. A lost key was a disaster.

I was back in B-block a few days later, responsible for half of Q-gallery, on the flats, as well as the center gate—the main access point from the flats to the galleries above. To learn this job, I had to handle the keys. But while the regular officer, a fat, powerful-looking cigar chomper named Orrico, was at pains to explain the job, he was not handing me the ring of keys. Instead, he played with them, twirled them around a big finger, caught them in his meaty palm. There were several, I could see: the cell key, the brake-padlock key, a gym-door key or two, an end-gate key, a center-gate key, a fire-alarm key, and at least one other, all of them different. The pewter-colored cell key was the biggest, its shaft as thick as a Mont Blanc pen, with a silver dollar-sized handle at one end and skeleton key-like chiselings in a tab at the other.

In case of a red-dot emergency, Orrico was saying, I was to get to the center gate as soon as possible. It was the main passage to the upper floors, and I would need to let through all the officers who had to pass, then lock it back up. In no case was I to follow the responding red-dot officers upstairs—even if my best friend worked up there, even if I heard officers screaming out in agony—because control over the gate was essential to the block’s security.

Concluding his lecture, Orrico left to pursue a cup of coffee and handed me the keys. No sooner had he disappeared than the red-dot alarm sounded. Officers were dashing toward the center gate, arriving before me. I rushed through them to open the gate, then realized I had no idea which key to use. My heart rate soared as I stood there fumbling with the key ring while more and more officers shouted at me to hurry up. “Somebody just take it!” I heard someone say.

I had just stuck the right key into the lock when the officers disappeared behind me. The alarm wasn’t upstairs, they’d realized, but through the short passage, to V-gallery. I peered around the corner and saw them massing in two huge piles, evidently on top of inmates. Then bang bang bang—on the center gate again. This time, officers were on the other side of it, responding from upstairs. Among them was my classmate Don Allen. “Come on, Conover, let’s go!” he yelled excitedly. I found the key again. I turned it. A second flood of officers pushed by me.

A few minutes later, everyone was back on his feet, including three mashed-looking inmates, who were handcuffed behind their backs. Each inmate had an officer holding the chain of his cuffs and marching him back to my gallery. First came a young black man with some swelling over his brow and a lot of blood flowing down the left side of his face. Next was a long-haired Latino with no shirt. Finally, there was another young black man, bleeding from gashes around the temple. They were to be locked in empty shower stalls on Q-gallery, and for that they needed keys.

Orrico appeared. “Where are they?” he demanded, holding out his open palm. I checked my belt. They weren’t there! I looked in the center-gate keyhole—not there either. My heart sank. “What?” Orrico demanded loudly. “You don’t have them?” This was the cardinal sin. Orrico called out to the milling officers, “Anybody got the center-gate key?” From the throng of officers came some questioning looks. Finally, Don Allen emerged holding—God bless him—my keys. Orrico snatched them away in disgust.

“You dropped them,” Allen said quietly. I had no idea how it had happened. Allen quickly and kindly changed the subject. He had seen part of the incident from above, he said. Apparently, the attacker was a V-gallery porter who had been sweeping the flats with a push broom. When another inmate appeared, walking down the flats, the porter attacked him, first breaking the broom handle over his head and then trying to gouge his face with the splintered ends. How the third inmate got involved, Allen didn’t know.

Allen had already seen a lot of action. “You heard about the guy who hung up yesterday?” he asked me. I’d heard it mentioned at lineup, a minor news item; for seasoned officers, this was a mundane occurrence. “I was there when they cut him down,” Allen told me. “He’d tied his shoelaces up high on the bars, but I guess not high enough to kill him, so he’s there all pale going gaagaa-gaaghh.” Allen, a natural comedian, was so funny making this sound with his eyes bugging out that I laughed despite myself. “We cut him down, then we carried him to the infirmary. My God, this place is crazy.” Allen, who had previously worked in juvenile detention for the Division for Youth, knew from crazy.

He left me to my thoughts, which mainly concerned my own adequacy. There would be no official repercussions—no sergeant had seen what happened, and Orrico hadn’t turned me in. But the incident troubled me. Was I up to the job, to the frequent emergencies? A couple of days before, while hustling up a staircase to back up an officer who was arguing heatedly with an inmate, I’d slipped and my baton had popped out of its ring, bouncing loudly down the metal stairs to the hands of officers below—a total embarrassment. And now this. During various crises in my prior life, I had responded well, keeping cool when a friend broke his leg skiing or when a girlfriend lacerated her leg in a fall from a motorcycle or when something in the oven caught fire. I was the guy who, when someone tripped over the cord, caught the falling lamp.

Somehow, that didn’t seem to translate to prison work. I wondered about the reason. During those other incidents, my starting point was a calm, which was then interrupted. The starting point in prison, however, was stress, much of it born of hostility. Early indications were that I didn’t handle it so well.

With a seasoned officer named Martinez, I spent the next day on guard at the foot of the tunnel leading up from Tappan. The gate was outdoors, but there was a little shack next to it where I sat with Martinez. He was short and seemed tough. Around us were the abandoned original stone cellblock, boarded up but looking solid enough to last till eternity; the A-block yard, with a weight-lifting area and handball courts visible to us behind high chain-link fences; and a garden, which stood between us and the Tappan dorms. Martinez told me to watch out for inmates who were carrying more than they should be. A lot of contraband was passed between Tappan and Sing Sing, and most of it probably came through here, he said. As we chatted, he told me about a softball game he’d witnessed in which inmates from the two opposing teams went after each other with the bats. “Compare your baton to a baseball bat, and you’ll know why we didn’t rush in there to break it up,” he said.

We were relieved early and walked over to the chapel, where Martinez sat notarizing inmate legal documents for an hour. His brother, who looked just like him, was in charge of the chapel. Things were quiet, and Brown, a new officer from up north, offered to show me around the inmate-programs area in the basement. Reading a newspaper in the Hebrew Affairs Office was one of Sing Sing’s more celebrated current inmates, Dr. Charles E. Friedgood, a Long Island surgeon serving twenty-five years to life for murdering his wife—the mother of their six children and a stroke victim—with a massive overdose of Demerol. A week after he had sworn on her death certificate that she died of another stroke, a relative alerted the police that Friedgood was about to leave the country for London. They stopped the plane on the runway at Kennedy Airport and removed the doctor, who was carrying some $650,000 in negotiable securities, and jewelry that had belonged to his wife. He was headed to Europe, police said, to join his Danish mistress, a former nurse, with whom he had had two children.

Friedgood liked Brown, and had apparently spoken to him before about Judaism. “Yes, Mr. Brown, we’ll see about you!” he said, smiling, as we left. “Have to have you circumcised one of these days!”

Outside in the hall, I said, “Circumcised, huh?” But Brown seemed embarrassed, whether about the idea of circumcision, an inmate referring to his privates, or the suggestion that he had discussed conversion, I couldn’t tell. He didn’t say anything.

Martinez was the subject of our pre-shift OJT briefing two days later. Apparently, he had stopped an inmate passing through the gate and asked to see what he was carrying. When the man resisted, Martinez had wrestled him to the ground but was by no means in control of the situation. Two OJTs were among six officers standing nearby who, Martinez had complained to the union steward, did nothing to help him out. Finally, the officer driving a van that ferries disabled inmates and others around Sing Sing jumped out and helped subdue the man. Our training officer was angry, and during the regular lineup we were chastised by a lieutenant.

“You OJTs—and a lot of other officers—need to get more confrontational with these inmates,” he said. “If it means you need to get bloody, then get bloody.”

The next day, when I was working in A-block, a group of my fellow OJTs was ordered to pat-frisk inmates leaving the block. This was a common activity, which occasionally netted contraband such as marijuana, cash, or a weapon. Inmates had to place their hands up against the wall and spread their legs while we patted them down from collar to socks. Removing a hand from the wall before the frisk was complete constituted aggression at most other facilities, though at Sing Sing it usually prompted merely a warning. “You fucking OJTs are a pain in the ass,” an inmate apparently told one of my classmates while up against the wall.

“What?” the officer said.

The inmate took one hand off the wall and began to repeat the phrase but was immediately jumped by the frisking officer and several others. When I heard about it, I was proud, because it showed we weren’t wimps. The trainees who had failed to help Martinez probably just didn’t realize what was going on or what was expected of them. Certainly none of us, I now felt, after the lieutenant’s lecture, would hesitate to help a fellow officer in trouble.

I worked a day in Tappan with Officer St. George, who was waiting to be transferred up north. He was slow and flaccid, with the kind of world-weary negativism you might find in employees behind the counter of a fast-food restaurant at a highway rest stop. Though Tappan was a good post by most measures—relatively low-stress, relatively low-danger—he hated life at Sing Sing so much that at 3 P.M. he would hit the road to spend a single day off at home, which was six hours away, on the Canadian border. He’d take a nap the next day and then start driving again at midnight in order to make lineup at 6:45 A.M.

“What town?” I asked, and he shushed me—rightly: He didn’t want inmates to know anything about him. This was the reason we didn’t have our first name on our tags—only an initial—and didn’t reveal other personal information. The reasons for this were best summed up by a story, possibly apocryphal, that I’d already heard at the Academy but which St. George recounted again: A CO pisses off an influential inmate in his block. Three days later, the prisoner hands him a manila envelope. Inside are photos of the CO’s daughter at play on her swing set.

Most of the day, St. George sat at a desk facing the door to a stairwell and argued with inmates. He argued over whose turn it was to sweep and mop the floor. (The names were listed on a chart, so there didn’t seem to be grounds for disagreement, but the inmates could see that St. George had an endless capacity to argue, and probably figured they should take advantage of it.) He argued over when the television could be on, when inmates could cook in the kitchen, and whether someone could leave a box of personal stuff in a common area. And, in the day’s most interesting incident, he argued with an inmate who came in after working in the mess hall with his shirt stuffed with stolen food.

If the inmate hadn’t been greedy, I thought, he might have gotten away with it. But the buttons on his shirtfront could barely contain everything he had taken: two loaves of bread, twenty-four frozen waffles, and a ten-pound bag of apples. St. George made him take it all out and put it on the desk. Leaving the mess hall with food was theft of state property, an offense right out of the book. But St. George couldn’t decide what to do. Instead of writing the guy up, he proceeded to argue with him, and a dozen other inmates who gathered around, about the fate of the contraband. With the fervor of lawyers, the inmates tried to convince St. George that mess-hall workers were paid so little they deserved any extras they could find. (“That’s a good point, you know,” he told me.) One proposed that the officer simply divide the food evenly among the seventy-five inmates on the floor. “Nobody would tell,” he asserted with a straight face. Yet another, tired of arguing, tried simply to intimidate St. George. “You think it’s a good idea to piss off this many people with just you here, CO?” Not only did St. George fail to write this inmate up for making a threat; he later concurred with him, telling me, “You really could get a knife in your back at any time around here.” Of course you could, I wanted to say, but that wasn’t the point.

Still undecided, St. George called the mess-hall officer to fill him in. The man appeared to be about as concerned over the theft as St. George was. Certainly, he didn’t care about reclaiming the food. “Just write him up for 116.10,” I suggested. “That’s what the training officer told us to do.” St. George seemed alarmed. I think he had just remembered that the training officers debriefed the OJTs every day and reviewed the actions of regular officers. Suddenly he appeared to be afraid that I was going to tell our superiors about the incident. He placed all the food in a locker and told the inmates that he’d decide later what to do about it. When I got my lunch bag from the locker a while later, I saw that half the waffles were no longer there, and asked about it. “Aw, I gave them to him,” St. George said. “But don’t get me wrong about these guys,” he added. “I wouldn’t piss on ’em if they was on fire.”

At 11 A.M., a blustery Neanderthal named Melman showed up on the floor to help with the count. He was annoyed because he had just come back from a drive home to discover that a pot of stew he’d put into the communal refrigerator at the Harlem Valley Psychiatric Center had been eaten. He had a bad temper, he admitted, telling how last week he had drawn his baton on an inmate in the tunnel leading up from Tappan. He couldn’t wait to transfer, because, he said, “I don’t want to work at a place where you tell them to step in, and they say, ‘Fuck you, CO!’” I found myself sympathetic to that idea, to the sentiment that officers deserved better than they got here.

Like our training officer, this man was fond of referring to inmates, out of their presence, as “crooks” and “mutts.” The conversation left me thinking about the many reasons that an officer might come to regard inmates as savages. If a savage dissed you, what did it matter? And if a savage got hurt (particularly due to an error on your part), who cared?

On-the-job training lasted four weeks, and I’d had several difficult days on galleries by the time, on my second-to-last day, I was assigned to work B-block’s V-gallery with Officer Smith. (V. SMITH, it said on his name tag—I didn’t learn his first name until I noticed it on his time card weeks later; and even months later, when we had become friendly and were swapping shifts, I never used it. That’s just how it was in prison.) The days on the galleries had been uniformly dispiriting. It was an impossible job, was the thing—it would probably take months for an officer to gain any real measure of control. Some of them were too lax, some too brittle, some careless, some too firm, some inconsistent. A gallery was such a huge challenge that it didn’t take long to see the ways in which an individual officer didn’t measure up. I wasn’t sure it was even possible to be a truly competent gallery officer.

Smith had at least three advantages over the others. His gallery was half the size of most—only one side of the cellblock, down on the flats. He was in charge of about sixty inmates. Also, he had chosen the gallery. Although he had only ten months on the job, nobody more senior had wanted it, so it was his regular post. He knew the inmates, and the inmates knew him. Last, it seemed to me that Smith succeeded because he viewed the inmates as human beings and was able to maintain a sense of humor in the face of the stress of prison life—traits that are two sides of the same coin.

With his shaved head and muscular build and his habit of holding his arms crossed in front of his big chest, Smith looked like a black Mr. Clean. He was married and lived in Harlem. He moonlighted as a dry cleaner: He collected dirty uniforms in the parking lot at the end of the day and brought them back pressed, for which he charged $3.50 apiece. He’d graduated from a public high school in the city and worked summers as a lifeguard.

Smith was talkative and tried to answer all my questions. He gave me the keys to the south end of the gallery, and he took the north. Our first order of business was to take individual cells off nighttime deadlock for the morning chow run. (The cells would still be held shut by the brake.) I turned the big cell key in more than thirty locks and finished before Smith; he was stopping at several cells to say good morning, I noticed. During the next hour, we listened as gallery letters were called over B-block’s public address system, which squawked so unintelligibly. Smith explained that on weekdays, the order was, roughly, top to bottom; Q and V galleries would go last.

Finally, V chow was called, and Smith and I each pulled a brake lever, releasing our respective sides. Hungry inmates emerged up and down the gallery, closing the cell gates behind them in a chorus of metal-on-metal thumps. Many inmates greeted Smith as they passed. This was so unknown, in my experience, that I wondered if he was too soft, if he gave them too much free rein. The real test, I knew, would come upon the inmates’ return from mess hall, when they’d have to do something they were never keen on doing: lock back in.

While we waited, Smith talked. He himself had had a use-of-force on his second day of OJT, he told me, down in Tappan. It was much like the one I’d heard about in A-block a few days before: An inmate took one hand off the wall during a pat-frisk, was warned by Smith, and then did it again. Smith crunched him against a wall, and a shelf of the inmate’s books came tumbling down in the process. His sergeant wasn’t quite as celebratory as ours had been. “He wrote that I was ‘excessively aggressive,’” Smith said, sounding a bit offended.

He told me about a few of his inmates. Two had murdered policemen, and one supposedly was set to inherit a chunk of the World Trade Center but had murdered his brother (“He’s got clippings”). These guys were in for drugs; that guy did some kind of computer extortion. I loved hearing these histories, because officers were not supposed to know them. The idea was to protect inmate privacy and to ensure that officers treated all inmates the same—that we weren’t unduly harsh to the cop killers or child molesters or anyone else whose crimes might strike a nerve. Of course, there were unofficial ways of finding out, and sometimes the inmates themselves would tell you (though you couldn’t always believe them—the child molesters, for instance, always claimed they had done something else). But to my surprise, most officers seemed to have little interest in inmates’ histories. Smith was different. V-gallery was, for much of every week, his neighborhood, and he wanted to know who lived there.

A gate swung open at the gallery’s end, and the inmates began to return from breakfast. We took up positions among them, keeping our eyes open. Some went back into their cells promptly and voluntarily, but many talked, traded cigarettes, or even jogged away from their own cells to pass something to another inmate at the other end of the gallery. Smith waited a couple of minutes, then rapped his baton on a gate and shouted, “Lock in!” Half a minute went by, and he repeated the cry. By now, only a few inmates were out. Finally, Smith lifted up an arm and yelled “Lock in!” a final time before indicating that we should pull the brakes. The remaining inmates entered their cells, and the gallery was clear.

In four weeks, I’d never seen that, and I told Smith so.

“I thought it up in the car driving home one day,” he said. “I call it Presto. I tell them, ‘I’ll give you three warnings, but then it’s on you.’ If anyone’s still out, I write down his cell number, and”—Smith made a key-turning motion with his hand—“I lock ’em in.” Because this was the first step in keeplocking, it always got an inmate’s attention. Most knew that an officer wasn’t likely to fill out a misbehavior report over slowness to lock in, but they could never be sure. Smith, in a gesture that I would later realize earned him stature among inmates and yet accomplished his goal of discipline, would let them back out for rec if he felt he’d made his point.

After lunch, true to his word, Smith locked the cell door of an inmate who was late stepping in—but the inmate was taking such a long time that Smith locked it before he even got there. The guy was stranded out on the gallery, alone. He came over to plead his case with Smith, who, arms crossed and with a small smile on his face, heard him out. “I’m not convinced,” he finally announced. But an inmate down the gallery was waving his arm out between the bars. He wanted to plead his friend’s case, explain the extenuating circumstances. “Sometimes I’ll let ’em use a ‘lawyer,’” Smith explained to me as we walked over there, “but if the lawyer doesn’t change my mind either, sometimes I’ll lock them both up.” That might be an interesting reform for American courtrooms, I thought. As Smith stood listening to the lawyer’s explanation, I heard him say, looking bemused, “If you’re gonna give me bullshit, at least give me good bullshit.” In the Case of the Lone Lingerer, the lawyer didn’t convince him, either. But this time, Smith didn’t lock him up.

Things hadn’t always worked so smoothly for him, he told me. At the beginning, the inmates had been difficult, and some sergeants had given him a lot of “ass-chewings.” But worst of all, surprisingly, had been other officers. One, named L’Esperance, who had worked V-gallery before Smith, disapproved of the way he ran it and, upon becoming gate officer stationed at the north end of Q-and-V, let everyone know about Smith’s supposed shortcomings—to the point of taking OJTs aside and telling them. Smith would leave at the end of the day with pain in his face and neck, which he only later realized was due to stress.

The model of an officer in total control was a lie, Smith said. “Did they tell you in the Academy about the guy who’s in such tight control of his gallery that you can usually find him with his feet up on his desk?” he asked. “Well, that’s a myth.” Even the best officers, he said, had to scramble around to put out fires; it was just a question of degrees.

Officers critiqued the permissiveness they perceived in each other more than any other quality. In a profession that placed a high value on control, that made sense, but I also could see how, in a case like Smith’s, permissiveness was a charge that a stupid and unimaginative CO might level against one who was effectively flexible. To me, Smith didn’t seem permissive. But sometimes he achieved his ends by engaging in a dialogue instead of simply saying no. Later that day, for example, when the keeplocks were returning from “keeplock rec”—the hour they were allowed each day in a fenced-off section of the yard—and passed briefly through the south end of V-gallery, two of them wandered up our way. They were not supposed to. Together we approached one, who begged to be allowed to pass by us in order to go speak to a friend, but he was refused by Smith. “Come on, man!” the inmate implored. Some discussion ensued. Near the end, Smith said, “I know you got to do your twenty-four hours; just let me do my eight.” The man said okay and left.

The other keeplock was standing at the bars of a friend’s V-gallery cell, chatting away, when Smith approached. Not saying a word, Smith moved closer and closer, acting as a party to the conversation and entering the inmate’s personal space until he stepped back in frustration. “They can’t stand it when you do that,” Smith said with a wink as the keeplock retreated.

Smith kept explaining things to me up till the very end of the shift. During the last hour—often a “freebie” period, when most inmates were out at rec or at their programs and their cells were deadlocked—most gallery officers found a chair and another CO to chat with. But Smith waved at me to join in a conversation he’d started with one of the few inmates left in his cell. He was Big D—Dominick Dwight, the computer embezzler. Smith had told him that I had some questions, and Big D, Smith said, might have some answers. I raised an eyebrow at what would have been considered heresy in the Academy—we’re going to listen to an inmate’s thoughts on how we should do our job?—but Smith said to go ahead.

This wasn’t his first bid, Big D explained. (Inmates used the same slang word for sentence that we used for elected post.) He had also done time at Attica, Clinton, and Wende. Even though he knew it made inmates nervous when there was a corrections bus outside waiting to take them to one of those places, he said that he and most others preferred them to Sing Sing because they were more orderly. Sing Sing was chaotic, he thought, largely due to its proximity to New York City and the number of recent transfers from Rikers Island. “They come in from HDM [a unit of Rikers] and they’re all full of it,” he said. With time and distance, men cooled down.

If inmates preferred to live mainly by the rules, I asked, then why did they give new officers like me, who were trying to enforce them, such a hard time? Why didn’t they appreciate a strict CO?

“Being a hard-ass just doesn’t go with the system here,” said Big D. “You’re not going to change everything.” And if you tried to make individuals do something they weren’t used to doing, he said, they’d feel unfairly singled out.

“You’ll get shitted down,” said Big D. “And the smell of that shit will stay with you a long time.”

On the other hand, he said, we couldn’t let them run all over us. “You give an inmate an inch, and he’s got a mile.” Smith said the trick was to be firm without being nasty or egotistical. Otherwise, you’d have simmering rebellion.

I left work that day happier than I’d been since starting at the Academy. After weeks of hanging out with senior officers who seemed to bring little more to the job than machismo and forbearance, who would say things like “If they’re happy, you’re not doing your job,” here was a guy—Smith—who saw gallery work as an art, something you could perform creatively. Interpersonal skills were a big part of it, though nothing like the IPC skills the Academy had described to us. Smith melded toughness with an attitude of respect for his inmates. In turn, he was respected back. What he seemed to understand was that at the root of the job was the inevitability of a kind of relationship between us and them—and that the officer played a larger role in determining the nature of that relationship.

At the Academy, this principle had never been mentioned. The job, we heard over and over, amounted to care, custody, and control: We gave the orders, in accordance with the rules, and inmates were to follow them. Simple as that.

In reality, of course, the jailer-inmate relationship was anything but simple. And traditions governing it, if in fact they existed, were vague. Take as simple a matter as saying “Good morning” to an inmate. One senior training officer, who happened to be black, had suggested that there was nothing wrong with such a greeting and that we ought to get in the habit of using it with our inmates. I had immediately flashed back to the Academy, where Officer McCorkle, describing his own gallery work, pointedly avoided saying “Please” or “Good morning” or any other pleasantry, and who, when greeted by his own inmates, informed them, “This ‘Good morning’ crap will cease!”

“They’re only nice to you because you’ve got the keys,” McCorkle had told us. Well, and they’re only jerks to you because you’ve got the keys, I’d thought. They’re the way they are and you’re the way you are because you’ve got the keys. Now, where could you take it from there?

Many rap and hip-hop songs had lyrics referring to the “overseers,” meaning any kind of cops. The term derived from the days of slavery, when plantation overseers made sure that the work was done and the discipline maintained. Lots of officers, I thought, liked to think of themselves as overseers, as enforcers. A training officer had mentioned that several of us had already been the target of inmate grievances, and one officer had even received two. Di Carlo smiled—he was the guy, I knew, and he was proud of it.

Getting grieved wasn’t my goal. But neither was it to make the inmates like me. Another trainer, Luther, told us he once stepped up to a fellow officer whom he had seen give an inmate five and then walk down the hallway, arms over shoulders, with him.

“Hey, man, it’s a black thing,” the officer had told Luther.

“Bullshit,” Luther had replied. Referring to each side’s state-supplied clothing, he told us, “It’s a gray thing and a green thing, and nothing more complicated than that.”

Somewhere between those poles lay the way I wanted to be.

Two days after my time with Smith was Conversion Day, when we became regular officers. We had to don our dress-blue uniforms again for the occasion. I talked with Arno outside the QWL building. He’d finally abandoned his efforts to wear long hair and had cut it all off—he was clean-shaven, right down to his skull. He looked good but tired: He’d worked the three-to-eleven shift the night before and had only had a few hours’ sleep. But, he said, it had been an interesting shift. He’d been working the first floor of the Hospital Building when an officer in B-block was struck on the head with a broom handle by an inmate. Officers had brought the prisoner down to the Hospital Building, which also housed the disciplinary offices and the watch commander’s office, where most of the white-shirts hung out. There, from a room near the ER, Arno said, he and many others, including inmate porters, had heard a white-shirt shout, “You think it’s funny to hurt an officer?” and the guy responded with prolonged cries of pain. Arno said this went on for about twenty minutes. A month earlier, I would have reacted negatively to a story like that. But now, seeing how outnumbered officers were and feeling more like prey than predator, I found in the tale a grain of comfort.

The superintendent was coming down to speak with us, but first they wanted to show us a video the Department had made of our training class in Albany. It all seemed so long ago, and so transparent now too, as I watched us getting yelled at in the Academy halls and on the floor of the gym—the breaking us down in order to build us back up. And though military boot camp had been the model, it was arresting this time around to see how much it really was like prison.

There we were, in only a slightly more upscale way, doing all the things that inmates had to do: receiving our uniform allowance, waiting in endless lines for chow, getting counted, wearing numbers on our T-shirts during rec, getting sprayed in the face with chemical agents, enduring a nearly single-sex environment and constant supervision, and living by a zillion mindless rules. There was DiPaola marching in the funny mincing step we learned just for graduation—I remembered the day we discovered the note from Sergeant Bloom, penalizing our room for a tuft of fuzz left at the bottom of the trash can. “If he comes by here now,” Deep suggested, “let’s shit him down.”

Now, however, we were at the ceremonial crossroads between our infantilization and our investiture with life-and-death powers. Soon we’d be holding the keys. Lieutenant Wilkin conducted a brainstorming session with us in which he wrote on a big art pad our suggestions for improving CO training. To my surprise, maybe a third of my classmates thought the training should be longer (training for the state police lasted something like five months, we learned). No doubt the prospect of real work around the corner—many, like me, had to return at 6:45 A.M. Sunday morning—led to some sentimentalizing of our Academy days. Others suggested that a longer Academy would not be necessary if short classes weren’t booked into long class periods, leaving us to practice pool shots in the lounge for a couple of hours each day.

Our trainers got in the last word, telling the older women in our class that they’d better get used to being called Grandma and the black officers that they should become accustomed to hearing “You been workin’ in the white man’s house; you a house nigger.”

“Good luck” or “Godspeed” were what you might expect to hear at the conclusion of on-the-job training for some other kind of work. Here, our bon voyage had a definite CO flavor:

“You’re the zookeeper now,” said Officer Luther. “Go run the zoo.”