CHAPTER 5

SCRAP HEAP

You feel it along the walls inside, hard like a blow to the head; see it on the walls outside, thick, blank, and doorless; smell it in the air that assaults your face in certain tunnels, a stale and acrid taste of male anger, resentment, and boredom. You sense it all around in the pointed lack of ornamentation, plants, or reason for hope—walls built not to shelter but to constrain. In the same way that a murder forever changes a house, Sing Sing has its own irrevocable vibe, a haunted feeling surely unlike that of any other prison, one rooted in the ground and in history: thousands upon thousands of lashings meted out by my predecessors in the nineteenth century; hundreds of prisoners executed there by the state while strapped down in an electric chair built by other inmates; and for the untold numbers of prisoners who were locked inside, an enforced experience of the glacial slowness of time. The prison’s most famous warden, Lewis Lawes, called his memoir Twenty Thousand Years in Sing Sing—the number referred to the sum of the length of sentences of all the inmates under his supervision. “Within such cycles worlds are born, die and are reborn… . Twenty thousand years in my keeping… . Will they bring life and purpose to any of our twenty-five hundred men who are sharing in that tremendous burden?”

The view from some of the wall towers (or from a boat on the Hudson or from an airplane, the only other good perspective), offers a different sense of the passage of time. You can see pieces of everything from the 1820s stone walls of the original cellblock to the 1980s prefab of the Family Reunion Program trailers and the Quality of Working Life building, as well as the gaps where earlier structures have risen and been razed. Sing Sing is one of those rare American places where enough of the old has been left alone—preserved, incorporated into the present, or simply never swept away—to put one in mind of history. Contained in that 170-year-old architectural hodgepodge are many aspects of the modern history of prisons in the Western world.

A little after my arrival, I found out that the guard who had pointed across the river to a scar on a ridge and told me that it was where the stone for the first cellblock had been quarried was wrong. Sing Sing’s site was picked because marble and other stone were already there, underfoot. Not only could the material be used to build a prison, the state legislature reasoned, it could be quarried, placed on riverboats, and sold into the indefinite future, helping the prison turn a profit.

The year was 1825. The inmates and their keepers traveled by boat down the Erie Canal from the state prison at Auburn and then by freight steamer down the Hudson, where they landed on the east bank “without a place to receive or a wall to enclose them.” In charge of them all and entrusted by the legislature to build the new prison was a cruel but innovative disciplinarian, Elam Lynds. A former Army captain, Lynds had previously been the warden (or agent, in the usage of the time) at Auburn, earning wide recognition for refinements he made in methods for handling prisoners.

The infant country, not even fifty years old, was thinking hard at the time about better ways to punish its criminals. From England and Europe, the United States had inherited a system of mainly corporal punishment for crimes. As James S. Kunen has written, “Before independence, Americans generally flogged, branded, or mutilated those felons they did not hang. Except for debtors and such minor miscreants as vagrants and drunkards, people were held behind bars only to await trial or punishment, and not as punishment.” In England as late as 1780, there were still over two hundred capital offenses—among others, “stealing anything worth five shillings, felling a tree in someone’s private forest, robbing a rabbit warren, living for a month with gypsies, or picking pockets.” Hanging was commonplace.

But generally during this era, throughout the Western world, the nature of criminal punishment was undergoing profound change. The period between the late eighteenth and the mid-nineteenth centuries, wrote Michel Foucault, saw “the disappearance of torture as a public spectacle” and the gradual phasing out of corporal punishments. Less and less did society target the criminal’s body; rather, what we wanted to punish was his mind.

The leaders of the American movement to rethink the prison were the Quakers in Pennsylvania. As early as 1682, William Penn’s colonial government experimented with incarceration as an alternative to corporal and capital punishment. The Quakers’ goals were prevention of further harm to society, deterrence, and, by the early nineteenth century, encouragement of prisoners to engage in “penitent reflection,” which could result in their personal reformation. This was the beginning of an American innovation, the penitentiary. Philadelphia’s Walnut Street jail, and later, in 1829, its massive Eastern State Penitentiary—the first institution to bear that label—were designed as places for prisoners to spend the day entirely alone, with only daytime work projects in their cells and a Bible for company. The arrangement came to be known as the Pennsylvania—or “separate”—system, and it attracted much attention, both abroad and at home.

Auburn Prison, meanwhile, had been built in the style of Newgate Prison in New York City, with inmates housed in “apartments” holding two to twenty inmates. Thinking that a version of the separate system might be just the thing for its most “obdurate and guilty felons,” New York began to build a new north wing of Auburn, composed completely of solitary cells. Elam Lynds became warden of Auburn while contruction was under way in 1821; on Christmas of that year, he moved eighty-three of his worst inmates into the new north wing. The regime he imposed was draconian: He subtracted the labor that kept Pennsylvania’s inmates occupied during the day in their cells, as well as the opportunity they had for daily exercise. The system turned out to be too harsh:

The governor pardoned twenty-six of the inmates, and the experiment was abandoned.

But Lynds was not discouraged. He modified the regime into something unique in the United States at the time: Inmates would be kept in individual cells at night but allowed to labor together in prison shops during the day, always in silence. This congregate system, or “Auburn system,” as it came to be known, produced more money for the public coffers than Pennsylvania’s (which allowed only individual work projects in the cell), and it drove fewer inmates insane. It soon became the leading model for prisons in the United States.

New York needed more prison space, and asked Lynds to build it. Newgate, in need of replacement, was only thirty-three miles from the village of Sing Sing, but Lynds didn’t want the inmates from there to build his new prison. He wanted a group from Auburn—men already accustomed to his brand of harsh discipline.

Sing Sing, stone upon stone. Lynds’s prisoners, under threat of the lash, put up temporary barracks, a cookhouse, and carpenter’s and blacksmith’s shops and started filling in shoreline for the prison yard. Then began the arduous work of raising the cellblock. Slowly it grew: four stories; eight hundred cells, 476 feet long. By October 1828, it was finished, Newgate sold, and the prisoners transferred. (Additional stories would be added in 1831—even in those days, the inmate population was growing faster than anticipated—and in 1860, bringing the total to six, with twelve hundred cells.) Tales of Lynds’s feat—of inducing inmates to build for themselves the largest prison in the land while unmanacled, uncontained by a prison wall—spread across the country and abroad. Of the foreign emissaries who would stop by to take a look, two Frenchmen were among the first.

Alexis de Tocqueville is famous for his seminal book Democracy in America, but what is less well known is his original purpose in coming to the United States. The young aristocrat and his friend Gustave de Beaumont had been dispatched by their government in 1831 with the specific mission of examining America’s rumored-to-be-innovative prisons. After their arrival in New York City, the “Mount-Pleasant State Prison,” informally known as Sing Sing, was their first stop.

Their first sight of it, on May 29, left a vivid impression, wrote George Wilson Pierson, Tocqueville’s principal biographer. “The place was bathed in heat and an unnatural silence, and there was an unmistakable undercurrent of terror in the silence. Mingling with the handful of keepers and watching the inmates at work, the French commissioners themselves became afraid.” To the Frenchmen, “accustomed to the fortress-like houses of detention and the old-fashioned walled prisons of France, it was an extraordinary sight.” The nine hundred inmates were all around the unfinished cellblock, unrestrained by chains and all engaged in hard labor—and yet, despite the absence of any wall (a few armed guards were stationed around the perimeter)—“they labour assiduously at the hardest tasks,” wrote Beaumont to his mother. “Nothing is rarer than an [escape]. That appears so unbelievable that one sees the fact a long time without being able to explain it.”

As the prison staff proudly explained to them, it was the separate system and the use of force that enabled the strict control they saw. Whippings, the keepers said, were administered five or six times a day. And, whatever its justification in terms of inmate penitence and self-reflection, the Frenchmen immediately appreciated the administrative power of the separate system. “All strength is born of association,” wrote Beaumont, “and 30 individuals united through perpetual communication, by ideas, by plans in common, by concerted schemes, have more real power than 900 whose isolation makes them weak.”

Also, they soon saw that the physical force was abetted by a moral one. Soon after their arrival, Tocqueville and Beaumont heard a story that appeared to shed further light on the keepers’ ideology. Apparently, Lynds had heard of an angry inmate who had threatened to kill him. Never letting on that he was aware of the threat, Lynds ordered the man to give him a shave in his bedroom. The prisoner lost his nerve and obeyed. When he was finished, Lynds dismissed him with words to the effect: “I knew you wanted to kill me; but I despised you too much to believe that you would ever be bold enough” to do so. “Single and unarmed, I am always stronger than all of you.”

The two Frenchmen asked Lynds what quality was the most important for a prison director.

“The practical art of conducting men,” he answered. “Above all, he must be thoroughly convinced, as I have always been, that a dishonest man is ever a coward. This conviction, which the prisoners will soon perceive, gives him an irresistible ascendency, and will make a number of things very easy, which, at first glance, may appear hazardous.”

Lynds’s achievement—the seemingly total subjugation of a large group of violent inmates—is one that would probably dazzle most correction officers and wardens today. The erection of Sing Sing offered a spectacle of total control. And yet by the time they left, Tocqueville and Beaumont had their doubts. In his diary, Tocqueville wrote, “We have seen 250 prisoners working under a shed, cutting stone. These men, subjected to a very special surveillance, had all committed acts of violence indicating a dangerous character. Each, at his right and at his left, had a stone-cutter’s hache [a hatchet or ax]. Three unarmed guards walked up and down in the shed. Their eyes were in continuous agitation.” The prison chaplain, he noted, “likened the warden of the establishment to a man who has tamed a tiger that one day may devour him.” And in their final report to the government, Tocqueville and Beaumont wrote,

Though they did not say so to their hosts at Sing Sing, Tocqueville and Beaumont were finally dismayed that “whilst society in the United States gives the example of the most extended liberty, the prisons of the same country offer the spectacle of the most complete despotism.”

“Do you think one can manage without corporal punishment?” they had asked Elam Lynds.

“I am completely convinced of the opposite,” the agent replied. “I regard punishment by the whip as the most effective and at the same time as the most humane, for it never makes a man ill and compels the prisoners to lead an essentially healthy life. … I do not think you can control a large prison without the use of the whip, whatever those may think who only know human nature from books.”

While a simple brute could never have prevailed over his men the way Lynds did, brute force was certainly indispensable to his rule. In the early years, Lynds was allowed to punish as he saw fit, and a whispered word, a look askance—the slightest infraction—was grounds for a whipping. Once the cellblock was occupied, whippings were administered in an area of the ground floor called the Flogging Post. Two iron rings had been fastened to the wall; hanging nearby were a number of the whips, known as the cat-o’-nine-tails, and—according to one inmate account—a gag. The inmate was stripped, his hands were tied to the rings, and then, to use a modern phrase, it was payback time: The keeper he had offended administered blows to his back.

Levi Burr, an inmate imprisoned for perjury, published a detailed memoir in 1833. Sing Sing, he charged, was a “cat-ocracy.” The cat-o’-nine-tails was generally made of six strands of hard, waxed cord, sometimes metal-tipped, that were attached to a hickory handle about a foot and a half long. The cords were “almost as hard as a piece of wire,” Burr wrote. While Beaumont had speculated that the fear of upsetting the inmate population would make keepers moderate in their use of the cat, Burr wrote,

In 1841, according to one legislative report, “More than a hundred blows were struck daily… . The whipping post was never dry.”

Men ate in their rooms, which were a claustrophobic seven feet high, six feet seven inches deep, and three feet three inches wide. There were no windows, no heat, and no running water. A small amount of light and air passed through the pattern of one-inch-square holes in the doors. Inmates slept on straw mattresses atop iron bed frames attached to the wall. (One hundred years after its construction, the original cellblock was still in use. Bank robber Willie Sutton wrote that in 1926, it “had uneven jagged stone walls that sweated moisture all day and all night.”) Inmates ate with their fingers; food was doled into a small bucket, called a kid. They were issued a single set of striped clothes, regarded as a humiliation (as well as a visual aid to assist the pursuit of escapees) and washed once a week. From Saturday evening until Monday morning, inmates were locked in their cells; this was the keepers’ only time off. Every morning, the keepers marched each gallery’s prisoners to an outdoor latrine to dump their tall iron slop cans, or night buckets, which each man carried in his left hand. This march had a special character. It was the lockstep, an Auburn innovation, in which the prisoner’s right hand rested on the shoulder of the man in front of him; his footsteps were short and synchronized, and his gaze was straight ahead—upon penalty of the lash.

“There are daily about twenty men on guard,” wrote Burr,

Slabs and chunks of marble were transported on carts that were pushed and pulled by prisoners up and down the steep hillside. “Several men grab a chain to pull a cart uphill,” wrote Burr, “two men hold ropes to guide it downhill.”

The sight of men being whipped as they struggled to move carts prompted consternation among a legislative committee convened to examine the prison in 1832, with particular attention to the system’s harsher aspects. Starvation of men as another means of breaking them, and the floggings for which Lynds had been famous, were viewed by the legislative panel as less innocuous than he pretended.

  A report from 1839 included the following testimony:

Lynds resigned in 1830, returning to Auburn in 1838. But his aura of heroism had faded. He was asked to leave Auburn a year later, following the death of an inmate whom he had punished for feigning illness. The local coroner held that the death had resulted “from disease, the fatal termination of which was hastened by flogging, labor, and general harsh treatment, imposed by … Elam Lynds. …”

Still, Lynds was rehired at Sing Sing in 1843. By then, however, he seems to have been a wrecked man. He lasted only a few months before being fired following several escapes, including one in which inmates built their own boat (whose existence had been reported to him) and then sailed away in it. The public had also grown skeptical of the brutality of the Lynds regime. By his own accounting, around fifteen hundred lashings were inflicted per month, not including those he meted out himself. (“His rule was never to forgive an offense, but always punish and with the lash.”) And there was growing disapproval of his reluctance to allow relatives to visit or to exchange letters with inmates, his conviction that inmates should have no books other than a Bible and a prayer book, and other such harsh measures. One of his own assistants wrote the legislature to say

I find the decline of Lynds particularly interesting in light of a letter from a former doctor at Auburn, Blanchard Fosgate, who around 1851 wrote legislators a letter to share his observation that the practice of whipping had been wounding to more than just the prisoners.

Lynds’s belief that it was impossible to govern a prison without the cat was disproved in 1848, when use of the cat-o’-nine-tails was abolished by the legislature and the prison continued to operate much as it had before. Corporal punishment in general was not renounced, however; other punishments increased in frequency to fill the gap, and the keepers invented new ones: They often attached recaptured escapees to a ball and chain, and might shave half their heads as a humiliation. Others were punished with the yoke, a flat iron bar weighing thirty-four to forty pounds, to which both outstretched arms were attached behind the neck; the pressure against the cervical vertebrae, even to a strong man, quickly became unbearable. (“I think that not one man in a thousand could stand up under the 40 pound yoke for four hours,” a keeper named John Ashton told the inspectors. A legislative committee in 1851 learned of one Sing Sing inmate who, punished for poor work with four hours of the yoke, was in such pain that he couldn’t leave his cell for two weeks; when he did return to the shop, he promptly cut off the fingers of one hand.) The iron cage, another means of physical punishment, was a round metal construction that the keepers placed over the inmate’s head and locked around his neck; it made movements of the head increasingly painful and rest impossible. Darkened cells were a frequent penalty. But the most common, and most feared, new punishment was the cold-water bath.

This procedure, whose contrast with the famously subtle Chinese water torture shows that American justice was perhaps still more interested in punishing the body than the mind, involved stripping the offending inmate and seating him on a bench, with his hands and feet secured in stocks. About four and a half feet above his head sat a barrel, filled completely or partially with cold water, depending on the offense and the mood of the keeper. In the early years of this punishment, the water—which could be icy cold in winter—was released all at once upon the naked inmate, delivering a terrible shock. In later years, it was released with less violence but was often collected in a wooden hopper placed around the inmate’s neck, in which it could rise to a level above the inmate’s mouth and nose. The keeper controlled the water’s release from the hopper, and used it to produce a sensation of drowning. The punishment was popular among prison officials because inmates so feared it and because it left no disfiguring marks.

Auburn physician Blanchard Fosgate attested that while the cold-water bath seemed hardly to affect some inmates, others showed damage both lasting and profound.

In 1851, Sing Sing’s administration reported giving 138 coldwater baths. In 1869, after a huge riot involving several hundred inmates in which many inmates and one officer were killed, a law was passed prohibiting its further use.

Certainly, outlawing barbaric punishments was evidence of progress in penal practice, and perhaps of progress in American civilization as well. But Rev. John Luckey, a Protestant minister who spent at least fourteen years as Sing Sing’s second chaplain, saw how it was eclipsed in importance by the character of the guards. Luckey, who has been called “the first social worker” for his research into inmates’ family backgrounds, wrote in 1860 that “much more depends upon the sound judgment and humane feelings of the disciplinarian than upon the instrument of punishment which he employs;—hence, a cruel man should never enter within the walls of a prison, except as a convict.”

The strict disciplinary measures of the nineteenth century served not only order, but profit. Previous systems had been—as they are today—a huge strain on taxpayers; from its beginning, Sing Sing had been conceived of as a moneymaking venture. After the establishment of the marble quarry came the construction of a wharf and of several buildings that housed industrial and craft shops. Over the years the prison shops produced toys, buttons, woven items including carpets and tapestry, cooperage (wooden barrels and tubs), brass, saws and files, boots, saddles, cast iron, cigars, furniture, hats, brushes, windows and doors, printing, knitting and hosiery, mattresses, and, as late as the 1980s, plastic bags. “A big business enterprise,” a prominent journalist called it; until 1884, a handful of contractors paid the state set sums for the labor of a certain number of men and then endeavored to get everything out of them they could.

The system was subject to numerous abuses. The agent and the keepers were bribed, in money and in goods, to offer special treatment to certain contractors; inmates were paid on the side to work beyond the prescribed hours, often at risk to their own health. James Brice, another white-collar perjurer who served time in Sing Sing in the 1830s and wrote a pamphlet about it, described contractors gathering in the blacksmith shop when new inmates arrived—they were there to have leg irons removed—to choose the ones they most wanted. Reports showed that at the behest of contractors, inmates were sometimes punished for poor work and that some contractors were even allowed to brandish the whip. The huge demand for inmate labor kept the prison overfull, while Clinton prison, far from downstate markets, was partly empty.

The contractor system was abolished in 1884, due in part to these perennial abuses but also because of the opposition of unions. Prison-made goods had an unfair cost advantage in the marketplace. (The state continued to use inmate labor but restricted it to products that the state itself could use—a practice that continues to this day, with the manufacture of license plates, garbage bags, office furniture, highway signs, and printed materials.)

That abolition made another group happy, too: businessmen in the town of Sing Sing. Ever since the prison had officially changed its name from Mount Pleasant to Sing Sing, shortly before the Civil War, local artisans and manufacturers had felt that the prison goods’ MADE IN SING SING labels stigmatized their products. In 1901, in fact, in order to more fully disassociate itself from the infamous prison, the town changed its name to Ossining.

Ironically, in 1970, the state—fleeing a similar historical burden—changed the prison’s name to Ossining Correctional Facility. The new name didn’t fool anybody, though, and never entered common usage. Besides, the game of name tag was about to come full circle: By the early 1980s, a group of businesspeople decided that the name Sing Sing might attract tourists. Before long, they petitioned the state to change the prison’s name back to Sing Sing, and in 1983, the state did.

The arrival of the electric chair in 1891 marked the beginning of the grim period for which Sing Sing grew world famous: as a center for executions. From August of that year, when four men were executed in one day, to 1963, 614 people were electrocuted at Sing Sing.

The first execution by electrocution had actually taken place eleven months earlier, at Auburn. Though now considered anachronistic, in the late nineteenth century the chair was thought to be a bold and humane innovation. Electricity harnessed for the human good was making its debut, first in a lightbulb in Thomas Edison’s lab and then, gradually, in cities across the land that were equipped by the Edison Electric Light Company with power lines and generators. It was thought to hold promise for medicine, too: Edison marketed his inductorium, an induction coil, as a guaranteed cure for rheumatism, gout, nervous diseases, and sciatica.

At the same time, doctors and scientists were aware of electricity’s power to kill. In Buffalo in 1881, Dr. Albert Southwick, a dentist, saw an elderly drunkard touch the terminals of an electrical generator; he was amazed by how quickly and apparently painlessly the man was killed and described the episode to a friend, state senator David McMillan. Also in Buffalo—soon to be dubbed the Electric City of the Future—Dr. George Fell developed a method to help the ASPCA electrocute unwanted dogs. McMillan spoke to Governor David B. Hill, who asked the state legislature to consider whether electricity might somehow replace hanging.

Around this time, in 1887, a New York murderer was put to death the old way—on the gallows. Roxalana “Roxie” Druse, of Herkimer County, New York, had murdered her husband in 1884 in a particularly grisly way. Following an early morning argument, she had enlisted their daughter to help her get a rope around his neck and then fired two shots into him. The bullets did not kill the man, and Roxie somehow intimidated a fourteen-year-old neighbor boy into shooting him again. Still her husband lived. This time she wielded an ax, and despite his cries of, “Oh, Roxie, don’t!” she chopped his head off. After further dismembering him, she spent several hours burning the pieces in a stove.

Despite the lurid details, Roxie Druse became something of a cause célèbre—no woman had been executed in New York in thirty-nine years. Petitions arrived in the governor’s office, asking him to commute her sentence to life imprisonment. The governor postponed the hanging but ultimately refused to reduce her sentence, and in February 1887, Roxie Druse was hanged in the Herkimer County jail.

The hanging did not go well. In front of a large crowd of reporters and others, Roxie Druse, wearing a pretty dress decorated with roses sent by her daughter, began to moan, weep, and then, when the black hood was pulled over her head, to shriek. When the trapdoor fell, Druse was killed not by a quick snapping of the neck, as was supposed to happen, but instead by slow strangulation as she dangled and writhed, conscious, for fifteen minutes at the end of her rope.

The death of Druse gave new life to efforts to reform New York’s capital punishment, and in 1888 the legislature, hoping to burnish the reputation of the Empire State, established “electric execution” (electrocution was not in common usage yet) as the state’s official method. The law went into effect on January 1, 1889. In March of that year, a Buffalo fruit vendor named William Kemmler, enraged at his common-law wife, murdered her with a hatchet in front of her young daughter, and he soon became the first person in the world sentenced to die by electricity.

By this time, Thomas Edison was locked in a fierce fight with George Westinghouse over their competing technologies: Edison’s direct current (DC) was quickly losing ground to Westinghouse’s alternating current (AC), which, time would prove, held many advantages for long-distance transmission. Unlikely to win the battle on its merits, Edison devoted considerable resources to trying to discredit AC in the realm of public relations: AC, he and his supporters asserted, was much more lethal than DC.

In Kemmler’s death sentence, Edison heard the knock of opportunity. He wanted to make sure that what he called “the executioner’s current” would be George Westinghouse’s AC. Worried by the plans to use his company’s equipment in the execution of Kemmler, Westinghouse apparently underwrote an expensive legal appeal of Kemmler’s conviction, which went all the way to the U.S. Supreme Court, where it was argued that electrocution would constitute “cruel and unusual punishment.” Kemmler’s appeals were denied, however. On August 6, 1890, he entered the new AC-equipped execution chamber at Auburn prison.

Public excitement and controversy over the execution were said to approach that of a presidential election. Awaiting Kemmler in the chamber were twenty-six witnesses, including six doctors, the district attorney who had prosecuted him, and many journalists; they were arrayed in a semicircle around the electric chair. Kemmler appeared with the warden from a side door, dressed in yellow trousers, a gray jacket, and a black-and-white-checked bow tie. The top of his head had been recently shaved and “had the appearance of a great scar,” according to The New York Times. “Gentlemen,” the warden said, “this is William Kemmler.”

Kemmler bowed and said ceremoniously, “Gentlemen, I wish you all good luck. I believe I am going to a good place and I am ready to go.” He bowed again and started to sit in a normal chair next to the heavy three-legged oak electric chair. The warden redirected him, then cut a hole in the back of Kemmler’s shirt, near the base of his spine, where an electrode would go. He began to attach the electrode, and another, on top of Kemmler’s head, with leather straps.

“Now, take your time and do it all right, Warden. There is no rush,” said Kemmler, urging the warden to make the straps on the head electrode a bit tighter. “I don’t want to take any chances on this thing, you know.”

“All right, William,” answered the warden. When he was finished, he walked to a door behind the chair and whispered to the electrician working the generator, “Is all ready?” Then he turned back to the room and said, “Good-bye, William,” the words being a signal to the technician to throw the switch.

To the horror of the witnesses, the first seventeen-second shock did not kill Kemmler. Doctors thought it had, but then they noticed blood pulsing from a wound where his index finger had contracted and cut deep into his thumb—a sign that his heart was still pumping. Two minutes after the current had been shut off, Kemmler began to gasp and gurgle.

“Great God, he is alive!” someone cried as the witnesses rose from their seats.

“Start the current! Start the current again!” someone else shouted. This time the current was left on for more than two minutes, during which witnesses heard the grinding of Kemmler’s teeth and saw blood drops from burst capillaries form on his cheeks. The power occasionally ebbed due to problems with the generator, so Kemmler’s body would unpredictably slump, then sit upright again, every muscle straining against the straps. The D.A. ran for the door, gagging. A newspaperman from Washington fainted. The room smelled like cooking meat, and then like feces. Kemmler’s head started smoking and his clothes began to catch on fire. A blue flame flickered at the base of his spine.

The power was finally cut. For a long time, the body of Kemmler was left to cool; when finally it was taken from the chair, rigor mortis had frozen it in a sitting position.

Though the doctors later assured everyone that Kemmler had lost consciousness immediately, the newspapers were unforgiving. “An awful spectacle,” opined The New York Times, a “sacrifice to the whims and theories” of a “coterie of cranks and politicians.” “It is obvious that Kemmler did not die a painless death nor did he die instantly,” reported the Buffalo Express. “It would be impossible to imagine a more revolting exhibition,” said The Times of London. “The man was really killed by a clumsy stun,” reported Scientific American, “for which a dextrous blow from a pole ax would have been an expeditious substitute.”

Amidst the recriminations and finger-pointing from the doctors, scientists, and prison officials, one might have expected the demise of electrocution technology. Instead, it persisted and indeed at Sing Sing (which soon became the official execution site), the technology was refined. No newsmen were allowed in Sing Sing at the electrocutions of four men on July 7, 1891; prison officials claimed that each was dead within six minutes of entering the execution room. At the following execution, the electrodes were attached to the head and the calf, instead of the small of the back. A witness, though sworn to secrecy, revealed that “on the fourth application of current, the prisoner’s eyeball broke and the aqueous fluid ran down his cheek.”

Experimentation continued. In hopes of reducing the singeing of hair and flesh, a new electrode system—one originally proposed by Thomas Edison and Harold Brown to demonstrate the lethal nature of AC—was tried on the chair’s seventh victim: Instead of forcing electricity to pass from head to leg, officials immersed both of the inmate’s hands in a conductive water solution. The first and only inmate to be subjected to this method endured fifty seconds of torture before the power was turned off and he was found to be very much alive. The staff then removed his hands from the water, attached electrodes as previously, and killed him the old way.

Slowly, the problems were solved. Voltage was increased to deal with the highly various resistances of different individuals, amperage was reduced so as not to “cook” the flesh, wet natural sponges were employed to improve the connection between scalp and skin, and diapers were placed on the condemned. In 1958, a New York State Department of Correction (as it was then called) history asserted that “the method of execution has been carefully worked out and standardized over the years.” As though in evidence, it offered a degree of detail that could have been of little use to anyone other than an executioner. “An initial shock of 2000 volts is given for 3 seconds, dropped to 500 volts for 57 seconds, built up rapidly again to 2000 volts, dropped again to 500 volts for another 57 seconds, and again instantly raised to the initial voltage. The entire application takes two minutes.” Over time, twenty-five states, plus the District of Columbia, adopted the chair. (Lethal injection has since become the preferred method; as of early 2000, only Alabama, Georgia, and Nebraska still use electrocution as their sole means of putting inmates to death.)

Of course, there had to be somebody to run these machines, to check the nuts and bolts of executions, to study it like an art. In New York and New Jersey in the years 1890–1914, it was Edwin D. Davis, a quiet man of “high cheekbones and drooping black mustache” who would arrive at Sing Sing wearing “a Prince Albert coat and black felt hat.” Perhaps because of threats on his life, Davis changed his address frequently and refused to be photographed. While electrician at Auburn prison, he designed both the first electric chair and testing procedures for it that involved large slabs of meat. Davis patented the helmet and leg electrodes, and always brought with him to executions a black satchel of secret equipment, which he would let nobody see. In fact, the state tried to purchase his patents and secrets, afraid that he might die before passing them along. The hangman of the age of electricity appears in accounts of Sing Sing history as a character out of the movies, coming in from a foggy night to perform his gruesome work, then leaving without a good-bye.

Davis’s eventual successor was his former assistant, an electrician named John Hulbert. Though Hulbert was as close-mouthed as Davis and similarly averse to being photographed, more is known about him thanks to a memoir entitled Sing Sing Doctor, by Amos Squire, M.D., who presided over the executions of 138 men between 1914 and 1925, working closely with Hulbert, who actually pulled the switch.

Though Hulbert lived in Auburn and the two were not friends (Squire refers to him as Hilbert throughout), Squire observed him closely. He describes Hulbert as “short and stocky, apparently a man with perfect nerves and excellent constitution,” which would seem to be another way of saying that he could perform his job without letting his feelings get in the way. When he read newspapers, Squire noted, Hulbert “studiously avoided all crime news, lest he stumble upon something relating to a person he might afterwards have to execute.”

Over time, though, Squire saw Hulbert grow depressed, and says he urged him to stop doing executions. Hulbert replied that he needed the money, the $150 he got for each electrocution. “I never questioned that,” wrote Squire, “but I felt that perhaps the very horror of the occupation of executioner had a dreadful fascination from which he could not escape. Otherwise he would have found a way to readjust his life—before it was too late.”

The beginning of the end for Hulbert came on a night when, three hours before a scheduled 5 A.M. execution, two inmates escaped from another part of the prison. The escape “upset the entire staff and disrupted routine,” a routine upon which Hulbert evidently depended, because, Squire wrote,

According to the 1929 obituary in the Ossining Citizen Sentinel, John Hulbert used his prison revolver to shoot himself in the chest and temple. His family said he had been despondent over the heart attacks he had suffered recently and the death of his wife the year before. The obituary writer commented, “Mr. Hulbert never could be induced to relate incidents pertaining to the electrocution of criminals. He was averse to notoriety and his comings and goings from the Sing Sing death house were always cloaked in secrecy.

“Whether his work preyed upon his mind no person ever was able to observe from his actions.”

Except, perhaps, Squire and others inside the close-lipped world of the Death House. Squire’s Sing Sing Doctor concerns one of the more interesting periods in the prison’s history, the years between 1910 and 1930, which saw the abolition of the lockstep, striped clothing, and the rule against talking at work, as well as the practice of keeping inmates locked in their cells from noon Saturday until Monday morning. This era saw baseball teams organized among inmates, as well as the groundbreaking establishment of an organization of inmate self-government, the Mutual Welfare League.

Squire recognized that readers would want to know about the thing that made Sing Sing increasingly famous as an object of fascination and horror: the Death House. His impossibly conflicted role as prison doctor and co-executioner is an extreme example of the ambiguity inherent in many prison jobs, including guard, but it put Squire in a perfect position to tell the Death House story. His work began with making sure that Death Row inmates stayed healthy—not just for their own good but, perversely, so they couldn’t succeed in suicide and thereby “cheat the chair.” It continued, on execution day, with his certifying that the inmate scheduled to die was sane. (He excepted only one.) Next, he sat with the condemned man as he was strapped into the chair and gave a hand signal to the executioner, hidden from observers behind a partition, to throw the switch. After a period of time, usually less than thirty seconds, Squire would order the power turned off while he checked for a pulse. As most men still had one, he would then signal for power to be turned back on one or more times, until he judged the man to be dead.

Finally came the autopsy. At the time the electric-execution law was passed, questions persisted about whether electric shock would always prove fatal. Two cases were on record of men having been accidentally electrocuted and then revived by physicians, after several hours’ work. To make sure the chair had done its job, legislators required that the brain of execution victims be autopsied.

Grotesquely, the autopsy room was situated in the Death House, next to the cells of Death Row. Inmates there, having seen their acquaintance marched to his execution through an infamous little green door at the end of the hall and then hearing the sounds of the generator, next had to hear the sound of his skull being sawed open. Squire portrays himself as aghast—though he can hardly have been surprised—when one famous condemned murderer, Shillitoni, interrupted an autopsy by going mad in his cell, breaking his furniture, and tearing his bedding to shreds.

Though Squire didn’t touch on the larger principle of the Hippocratic Oath (First, do no harm …) and the matter of whether doctors should have anything to do with executions, he expressed discomfort about almost every aspect of his work. He regretted that he was “the only member of the prison staff who was compelled to watch the man in the chair every second,” and revealed that many times while listening for a heartbeat in the body strapped into the chair, “I have been so overwrought I was alarmed by the thought that what I heard was my own pulse rather than that of the dying man.” He conceded that

Squire devoted two chapters to arguing against capital punishment (“Each time a person is executed, the effect upon the public is infinitely more degrading than deterrent”), and he told of one sardonic man who on the eve of his execution said, “‘Boys, this is going to be a powerful lesson to me.’” So the reader gets a sense of a man who spent his professional life participating in something that he loathed and that—at least at the end—he did not believe in.

Squire’s Hulbertian decline began in a similar way—with disruption of the routine. One of the murderers scheduled for execution had had to be kept constantly in a straitjacket, and Squire, for apparently the first time ever, had sent the governor a letter expressing his doubts that the man was sane. When the day of the execution arrived, the governor still had not responded.

Panicked, Squire boarded a train to Albany to try to speak to him personally, only to learn that the governor was out of town and for the time being unreachable. Two hours later, though, Squire finally got him on the phone, and the governor ordered a two-week reprieve, during which experts reexamined the man and sent him not to the chair but to an asylum.

Did he want to touch the man to comfort him, I wonder, or to kill himself?

Having confided in a friend and then his daughter, Squire finally quit. “If I hadn’t,” he wrote, thinking of Hulbert, “I might not be alive today.”

The electric chair may or may not have been a more humane method of execution than hanging—Squire, who had seen two hangings in Canada, thought it was—but it seems it could not have been any better for the people who had to operate it. Then again, the well-being of those who would operate the electric chair probably never entered the minds of its promoters. I think this problem—not being taken into account—exists in some degree, however minimal, for nearly all people who work in prisons. Even a prison chaplain, one of the “good guys,” faces the underrecognized moral dilemma inherent in working in a jail.

Irving Koslowe, Sing Sing’s rabbi for forty-nine years (until 1999), attended seventeen executions, including those of the Rosenbergs, in 1953. The day before an execution, he told the makers of a historical documentary that aired while I was a guard, the condemned man was moved from the regular Death Row cells to a cell near the Dance Hall, through which he would walk on his way to the chair. His head was shaved. He ordered his last meal. By the time the guards came for him, Koslowe said, “that man was half dead.” One night after work, I watched Koslowe describe, on television, the minute-by-minute procedure preceding execution, heard how he told inmates he’d “be there” for them—“on a rubber mat, but I’ll be there.”

Could one really “be there” and stand on the rubber mat? I admired Sister Helen Prejean (Dead Man Walking) for her pastoral work among Death Row inmates. But the problem with being an official prison chaplain, it seemed to me, was that one had to accept the values of the system and could not, as a matter of practicality, question anything. Anyone holding the job was hopelessly compromised as any sort of moral example. Like Rabbi Koslowe, you had to agree to stand on the rubber mat. The documentary showed a sign over the door in the death chamber, which the rabbi had passed under many times. It said SILENCE.

The same dynamic, I realized, was at work for correction officers. You didn’t have to be flaying an inmate’s back with a cat-o’-nine-tails to be wounded by the job. That was simply its nature, a feature of prison work as enduring as Sing Sing’s cellblock design. “In its application the familiarity it causes with suffering destroys in the breast of the officer all sympathetic feeling”: The words of the Auburn physician seem to me to express a timeless principle.

When I was first looking into the lives of guards, somebody at Council 82 suggested I speak with the union’s chaplain. I was surprised to learn about Father James Hayes, and I liked him immediately. He said that he counseled members over the problems the job seemed to cause—alcoholism, divorce, wife and child abuse, ill health. He also mentioned counseling a guard who had put his finger on a sad truth that priests seem to understand better than doctors or social workers.

The CO was retired, said Father Hayes, but his retirement was troubled by the thought of what his life’s work had amounted to. “Father,” he said. “I spent thirty-three years of my life depriving men of their freedom.”

The priest told me he had nodded, listened, and prayed. There was nothing more to do.

Amos Squire’s tenure at Sing Sing coincided with that of two of its most famous wardens, Thomas Mott Osborne and Lewis Lawes. Osborne stayed only a few months; Lawes, more than twenty years. Osborne was at heart a politician and reformer; Lawes was a firm but sympathetic warden several cuts above the rest, a passionate believer in doing the job right. Both were from upstate prison towns. Both—though they oversaw Sing Sing’s executions—were against the death penalty.

A life-size bronze statue of Osborne stands, anomalously, in the foyer of the Albany Training Academy. Draped over one outstretched hand is a set of cuffs and chains; in the other is an open book. I say anomalously because to Osborne, guards were not people to be admired. In fact, he envisioned a prison system that would dispense with them altogether. New York’s prison system in the early twentieth century, to his concerned eyes, was in need of complete overhaul. “Prisoners are treated now like wild animals and are kept in cages,” he said in a lecture in 1905. “The system brutalizes the men and the keepers. [The inmates] are forced to work, and this is not reformatory. It does not create in the criminal a desire to work and respect the law. … I would propose a system [wherein] the prisoner’s sentence would be indeterminate. He would work for a living or starve, and if diligent would be allowed to save up and purchase luxuries and possibly freedom. He would be self-governing and learn to respect law.”

Osborne grew up in a wealthy household in Auburn, and, after attending prep school and Harvard, became mayor of Auburn, a newspaper publisher, and a manufacturer. A patron of young Franklin Delano Roosevelt, he held other state appointive offices before getting himself named chairman of the new State Commission on Prison Reform. He succeeded in having a political ally appointed as warden of Auburn prison and then had a brainstorm: He would enter Auburn for a week as an “inmate” and use the experience and publicity to launch a campaign for fundamental prison reform.

Osborne’s original plan was to enter the prison population anonymously, but he was soon dissuaded: Inmates would figure out his identity, he was told, and he would be taken as a deceiver, a spy, never to be trusted. So instead, he addressed all the inmates of Auburn in September 1913, a day before joining them. “I am curious to find out,” he said,

Anticipating criticism by observers outside prison, if not those within, he added,

Still, he argued in Within Prison Walls, a book recounting his experiences, our inability to ever put ourselves precisely in the place of another should not keep us from “constantly studying and analyzing the human problem. It still remains true that ‘the proper study of mankind is man.’”

Osborne openly adopted the nom de guerre Tom Brown for the duration of his imprisonment, and began his voluntary stay. His first-person narrative, written diary-style, attempts little dispassionate observation and, somewhat embarrassingly, reveals him ill prepared for prison life. He complains about having to sleep in underwear instead of pajamas—why couldn’t the state provide those?—about the gristle in his hash, about a feeling of claustrophobia in his cell (“If I were just to let myself go, I believe I should soon be beating my fists on the iron-grated door of my cage and yelling.”). The inmates around him seem generally to be a swell bunch of guys, and he shows only faint recognition that his prominence may affect their behavior toward him.

Yet despite his sentimentality and preconceptions, he came away with some shocking stories, particularly his description of Auburn’s “jail” or Box, and some keen insights. “Rigid discipline,” he decided, “… increases disrespect… .

By the same degree that he was popular among inmates, he appeared to alienate the guards. They mocked him, according to his inmate confidants, and considered him naive. He tried to evince some empathy for them in his book. (“I can conceive no more terribly disintegrating moral experience than that of being a keeper over convicts,” he wrote. “However much I pity the prisoners, I think that spiritually their position is far preferable to that of their guards. These latter are placed in an impossible position; for they are not to blame for the System under which their finer qualities have so few chances of being exercised.”) Still, beneath it his disdain was evident. “I should not like to be understood as asserting that all keepers are brutal, or even a majority of them,” he wrote. “I hope and believe that by far the greater number of the officers serving in our prisons are naturally honorable and kindly men, but so were the slave-owners before the Civil War.”

Upon his “parole” from Auburn, Osborne was praised in some circles and, as he expected, mocked and jeered in many others for “playing at” prisoner, for thinking it “necessary to wallow in a mud hole to know how a pig feels.” But it served his purpose of getting prison reform on the public agenda and strengthening his hand for the next phase of his campaign.

At the core of Osborne’s crusade was a belief that nothing inmates learned in prison really helped prepare them for independent lives outside. “It is liberty alone that fits men for liberty,” he liked to say, and with the thought that they needed to do more for themselves, he undertook the next phase of his work, helping Auburn inmates establish a form of self-government. The Mutual Welfare League, which slowly grew from this effort, was an administration-supervised means for inmates to run their own lives, from administering a system of discipline to organizing sports to starting a commissary where inmates could buy goods with a special League scrip. To the consternation of his many political enemies, and certainly Auburn’s guards, Osborne used his charisma and the credibility earned as an “inmate” to put this system into effect.

Osborne, increasingly a national figure, was appointed warden of Sing Sing on December 1, 1914. The previous warden had left after a corruption scandal, and such was Osborne’s renown that the Republican governor was willing to give him a try. Osborne began to institute familiar reforms but found Sing Sing more complicated than Auburn. Mutual Welfare League-style reforms threatened the entrenched power of certain inmates. His transfer of powers of self-determination to inmates provoked loud and repeated charges of coddling. The governor himself began to get irritated with Osborne over his repeated attacks on capital punishment—the warden made a point of being out of town whenever an electrocution was scheduled. Plots were hatched to discredit him, and before his first year was over, one finally snared him: a raft of charges alleging violation of prison rules, including one count that warden Osborne “did commit various unlawful and unnatural acts with inmates of Sing Sing Prison, over whom he had supervision and control.”

A main source of the sodomy testimony was an inmate whom Osborne had previously identified as a spy for the superintendent of prisons—one of his political enemies—and had transferred out. This man, Fat Alger, claimed to have drunk claret on the warden’s porch one night till 2 A.M. and then stayed in his bedroom till 3 A.M. Despite what some saw as the transparent falsity of the charges, Osborne was indicted by a Westchester grand jury. The sensational legal battle that followed utterly consumed him until, several months later, all the charges were finally dropped. He resumed his job as warden, only to resign three months later.

Though his profile was never again so high, and the institutions of reform he began were attenuated over the years, Osborne succeeded in shifting the course of American penal practice and modified the seemingly set in stone operations of two of the country’s biggest rock piles.

Thomas Mott Osborne’s inspirational tenure as warden of Sing Sing was typical only insofar as it was short. Until the 1950s, when it became a civil service post, the job was a political appointment, often bestowed on men who knew nothing whatsoever about running a prison. “The quickest way to get out of Sing Sing is to come in as warden” was a popular joke. Thirty-one Sing Sing wardens had lasted only little over a year; they included a steamfitter, a coal dealer, a horseman, a postmaster, a customs revenue collector, a millionaire and philanthropist, and “assorted ward-heelers.” Four years after Osborne left, however, a former guard from Elmira named Lewis Lawes took the helm and in twenty years on the job became America’s most famous and admired warden.

Lawes had started his career as a guard at Clinton prison and then returned to his hometown of Elmira, where he rose to the post of chief guard. And yet this guard’s guard was highly literate and open-minded. To him, Osborne had been an inspiration. “Of all the array of incoming and outgoing wardens in the century of Sing Sing’s history, [Osborne’s] name stands out in bold relief,” Lawes wrote in 1932. “To him must be given the credit for a more enlightened policy that, while not entirely complete, pointed the way toward the new penology.”

Though not primarily a reformer, Lawes had strong opinions about the possibilities of prisons. Osborne’s shortcoming, as Lawes saw it, was that he gave prisoners too much self-government too fast—and that some of what he gave should never be given at all. “There can be no democracy within prison walls,” Lawes wrote. “A group of men who have quarrelled with the law cannot be expected to set up a government patterned after the one they antagonized.”

Sing Sing’s Mutual Welfare League had quickly become the domain of gangs and cliques, Lawes said—an officially sanctioned Darwinian power structure. The more talented individuals who should have figured prominently would have nothing to do with it. The proper role of the League, Lawes believed, ought to be as a “moral force,” not an actual mechanism of self-government.

Gradually, Lawes shut down the League. In its place he established an administration distinguished by its humaneness and intelligence. Prison administration couldn’t help being a despotism, but it could be an enlightened one. “It quickly became apparent to me,” he wrote,

Like Osborne, Lawes believed that increasing public knowledge of prisons could only be good. Osborne had brought prisons to the public eye through his spectacular deeds; Lawes had other methods. The crime wave of the 1920s and 1930s, the great gangster era, increased public interest in prisons and punishment, and the interest of Hollywood in particular. Lawes obliged the industry by allowing Warner Bros. inside his prison. The film Angels with Dirty Faces (1938), starring James Cagney and Humphrey Bogart, was filmed partly inside Sing Sing, as were Each Dawn I Die (1939), with Cagney and George Raft; Castle on the Hudson (1940), with John Garfield and Ann Sheridan; and others, including two based on Lawes’s books Twenty Thousand Years in Sing Sing and Invisible Stripes. A recurrent theme was of “hard-boiled, but not incorrigible inmates who somehow came around under the compassionate, but firm hand of the warden.” The title of his book Invisible Stripes referred to the stigma that continued to hobble criminals after they’d done their time and left their striped uniforms for the streets.

Lawes wrote five nonfiction books in all; he also did radio broadcasts and contributed articles to magazines. Time and again he tried to drive home the idea that crime really begins in the slums, and that prison itself can’t cure it. For one Hearst Metro-tone newsreel he sat in his office, young inmates around him wearing masks to preserve their anonymity.

Lawes also invited major league baseball teams into prison to play against the Mutual Welfare League team, the Black Sheep. During one such game, Babe Ruth hit what has been purported to be his longest home run ever, 620 feet, over the prison wall.

When Lawes arrived in 1920, Sing Sing had a population of slightly over one thousand, all housed in the original cellblock. But the crime wave led to more inmates, and by 1927 there was serious overcrowding in all of the state’s facilities. Construction of all the main Sing Sing buildings in use today began in the early twenties: a new Hospital Building, a new Death House, 5-Building, and 7-Building. In 1926 it was decided to build A- and B-blocks on the hill, and in 1929 they were completed, along with the chapel and mess hall. Laundry and administration buildings followed shortly, then the school building and a new power plant. Lawes hired the first black guard in 1925 and endorsed plans to institute a six-day workweek for prison officers, down from seven.

Lawes ran his prison in a paternalistic way that had a warmth we would not recognize today. He met daily with representatives of inmate groups. Lawes’s children knew the inside of the prison from movies they watched there, and the inmates who worked in his house as cooks, cleaners, and handymen knew his family. When his wife died, in 1937, every single inmate is said to have filed out through gates past her casket in the warden’s house and then back into prison. In 1940, Lewis Lawes finally retired.

One thing had not changed while Lawes was at Sing Sing: the old cellblock. Amidst the controversies and corruption, the many wardens, and the advent of “penology”—including progress in prison architecture and conditions elsewhere—the massive structure sat immobile, barely altered in a hundred years except for growing more crowded (six hundred cells were double-bunked in 1909) and losing a floor and a half in a 1917 demolition bid that was halted after the state realized it still needed the space. Diseases like cholera, dysentery, and scarlet fever had haunted it from the start; in 1892, the same year twenty-seven inmates died there from tuberculosis, Dr. R. T. Irvine observed that the building offered “unusual opportunity for diffusion of this disease.” A 1905 State Prison Improvement Commission found the cells damp, too small, and badly ventilated, concluding, “verily, this is far worse than living in a sewer.” Yet, as the official department history put it, the cellblock “continued to hang like a millstone around the neck of the institution … continued to swallow thousands of inmates into its malevolent, malodorous maw”—over a hundred thousand men in its first century alone. Finally, in 1943, the last of the original cellblock’s inmates were moved out. Parts of the structure were used as a vocational shop until the roof burned down in 1984, when the building was permanently closed—boarded up and fenced in though, inexplicably, not removed. The prison continued to grow and operate around its historical core.

The 1950s and 1960s brought what has been called the professionalization of corrections—the idea that prison was something the working person might make a career of, whether as a “correction officer” or as a college-educated warden. Prison jobs became civil service jobs; prisons within the states became more standardized and centrally controlled; and unions in a few states, particularly New York and California, became important players. For officers, professionalization meant more training and implied a higher standard of on-the-job conduct. The self-image of the corps was remade, partly in the hope that a “professional” could command higher pay. As Sergeant Bloom had told us at the Academy, “If you want to act like a guard, go ahead—that’s easy. But if you want to be a correction officer and get paid like a CO, then pay attention.”

Professional administrators came to replace the politically appointed wardens of old. Though the change was long awaited, the advent of bureaucratic administration seemed to guarantee that the visionary tendency of an Osborne and the humane one of a Lawes were things of the past. The same qualities of imagination that the institutions seemed to require so badly were less available than they had ever been before.

Sing Sing moved in some ways into the future, incorporating a small number of vocational programs, a few school courses, a counseling staff, and expanded opportunities for inmate recreation. But this development was limited by a lack of space. The town of Ossining was now firmly packed around the prison’s great walls, which meant there would be no funds forthcoming for the modern industrial education shops that other maxes enjoyed, no room for a prison farm, such as the one run by inmates at Green Haven. In the meantime, as the prison aged, newer facilities looked that much better by comparison. The town of Ossining grew frustrated that it could collect no taxes on fifty-five acres of prime shorefront land. Throughout the 1970s and 1980s, repeated calls were made to close Sing Sing down.

A slow push was under way to reemphasize the rehabilitative possibilities of prison in New York State when, on September 9, 1971, the Attica prison uprising began. It was a tumultuous time in American politics—sixteen months earlier, the Ohio National Guard had killed four students at an antiwar rally at Kent State University. Barely two weeks before the Attica revolt, the California tower guard had shot to death Black Panther George Jackson, and the next morning Attica inmates refused to eat breakfast and wore items of black clothing in solidarity. Throughout the summer of 1971, Attica was jumpy; it took only a small confrontation in the yard between two inmates and three officers to spark the violent inmate takeover that would make history. But the rebellious inmates wished to get one thing straight at the beginning of their written statement of five demands: “The incident that has erupted here at Attica is not a result of the dastardly bushwacking of the two prisoners Sept. 8, 1971,” they wrote, “but of the unmitigated oppression wrought by the racist administration network of the prison, throughout the year.”

Governor Nelson D. Rockefeller refused to negotiate directly with the inmates, and on September 13, worried that the inmates were harming their hostages, the state police launched a bloody battle to retake the prison. Two hostages, it turned out, had been seriously injured by the inmates, but ten hostages and twenty-nine inmates were then killed by police in the attack. Three hostages, eighty-five inmates, and one state trooper were wounded.

With one hand Rockefeller continued to implement some of the previously approved reforms—drug-rehabilitation programs, college-degree classes—but with his other, he pushed through the Assembly a raft of strict antidrug laws. One effect of these laws was an increase in the prison population, over the next twenty-five years, of 560 percent. This explosive growth resulted in the building of fifty new prisons and the transformation of the Department of Correctional Services into the state’s second-largest employer, after Verizon. With all the new construction upstate, and the suspension of executions in 1963 due to legal challenges, Sing Sing was no longer where the public attention—or the cutting-edge practices (such as shock camps for teenagers or, in other states, privately run prisons)—was focused.

Its long history and gradual marginalization made Sing Sing increasingly different from the state’s other prisons. Lewis Lawes wrote of being wary of his appointment there in 1920, in part because when he had visited a few years earlier, as chief guard at Elmira, his recollection of it “was not altogether satisfying.” He went on: “There was, at that time, little attempt at cleanliness. The yard was littered with debris.” The air of neglect gradually if inexplicably returned after Lawes left; something about the place seemed to invite it. Around 1969, B-block, only forty years old, was condemned due to structural problems and abandoned. In 1973 Sing Sing itself was changed by the state from a maximum-security prison into a “reception center”—a place where new inmates would arrive to be tested and classified and then sent to the prison where they would ultimately serve their sentence. Then, due to a lack of cells in New York City because of the closing of the Tombs jail, it also became a stopgap holding pen for some of New York City’s overflow during the city’s financial crisis.

By 1982 Sing Sing had been reclassified once more as maximum-security. B-block was refurbished and reopened as a “transit block,” supposedly holding inmates for limited times. Shortly after this reopening came the 1983 incident in which Sergeant Wickersham and sixteen others were held hostage. Looking back for the reasons behind the B-block takeover, a state report commented that Sing Sing was by then “to most of the outside world … a relic from musty books and old movies, which many people were surprised to learn was still in use after 157 years.” It

By the late 1980s, Sing Sing’s status as a de facto training facility was well established. Its reputation for being loose and wild was ascendant. Four guards and a sergeant were indicted in 1982 on corruption charges, such as being paid to smuggle marijuana and cocaine into prison. Nineteen eighty-three brought the B-block takeover and hostage crisis. In 1986 a burglar and two murderers, having distracted officers with smoke bombs, escaped through a window of the school building onto the train tracks below, using wire cutters and a thirty-foot-long rope made of shoelaces. All this was followed in 1988 by the mortifying headline on page one of the New York Daily News that read SING SING SEXCAPADES and the banner inside that read SWING SWING:

The story said that random urine tests had shown that 21 percent of Sing Sing inmates were on drugs, compared to a statewide prison average of 6 percent.

Upon assuming the wardenship of Sing Sing, Lewis Lawes sat down with a stack of “musty reports and records that had not been looked at in decades.” As he traced the prison’s history, he saw progress, the “puritanical” practice of the nineteenth century evolving into the “more enlightened social thought” of the twentieth. But if you compare the state of America’s prisons at mid-twentieth century to their condition today, it is hard to make the case for any further progress at all.

As a former officer looking back into Sing Sing’s history, I was struck by lost institutions of the old prison, such as the bands that played as prisoners marched to chow. Early in the twentieth century, inmates who prized special bars sewn onto their uniforms for time served were humiliated when, as punishment, these symbols of accomplishment were removed. During World War II there were wildly successfully inmate blood drives—1,106 pints were donated in 1943. These all look like signs that inmates, though segregated in prison, still considered themselves a part of mainstream society in some way. As recently as twenty years ago, old-time officers told me, it would be exceptional to find more than ten B-block inmates on keeplock. Nowadays, the number is nearer a hundred, and the Box is always full.

Almost unarguably, prisoners’ attitudes about their punishment have worsened. Few seem to feel that the exchange of their time and liberty for their commission of a crime is a fair one, and many if not most continue to insist upon their innocence. And race has entered the equation, on the side of the inmates. Eldridge Cleaver, writing from Folsom prison in the sixties, observed:

The essential relationship inside a prison is the one between a guard and an inmate. Any true progress in the workings of a prison ought to be measurable in changes in the tenor of that relationship. The guard is mainstream society’s last representative; the inmate, its most marginal man. The guard, it is thought, wields all the power, but in truth the inmate has power too. How will they meet, with mutual respect or mutual disdain? Will they talk? Will they joke? Will they look each other in the eye?

The course of this central relationship is one that is hard to tease out of official investigations and even prisoner memoirs, but my sense is that it has evolved little, if at all. Nineteenth-century inspectors’ reports show that while guards as a mass were feared, individuals among them were liked and hated; in reports of punishments, it can be ascertained that some guards meted out a huge number, others, very few. Some guards were honest; others, clearly on the take. According to a legislative report from 1851, “The amount of compensation allowed to the officers is so small, that a high order of talent cannot be pressed into the service of the State… . We cannot expect all the virtues in the world for $1.37 a day.” That hasn’t changed much, either.

Even so, the author of the report saw how guarding could be done either poorly or well.

At Sing Sing, the century-old warning is still unheeded.

One day, after I finished my shift, a deputy superintendent gave me permission to look through two manila folders in which he kept a lot of old newspaper clippings and prison memorabilia. In one of them I saw a HELP WANTED poster published by the state in the 1950s to attract new guard applicants. It listed as job duties the usual supervision and custodial work, but there was also a line about helping to counsel and reform the prisoner. Nothing like that was ever presented to me during training. I think the Department is smart enough to know that today’s COs would only laugh.

But in their hearts, I think the officers wish it weren’t so. I think they’d rather chat with an inmate and reinforce his connection to the outside world than dodge missiles of shit and piss. I think the statue of Thomas Mott Osborne in the foyer of the training academy is there because, somehow, Elam Lynds won’t do. Osborne, the inmates’ friend, chains in one hand and book in the other, is the only hero corrections can possibly have. He is perhaps best known for this quote: “We will turn this prison from a scrap heap into a repair shop.” The presence of his statue, I think, speaks to an idealism that is never openly discussed by guards, the hope that prisons might do some good for the people in them, that human lives can be fixed instead of thrown away, that there’s more to be done than locking doors and knocking heads, that the “care” in care, custody, and control might amount to something beyond calling the ER when an inmate is bleeding from a shank wound.

Instead, the most recent trend in corrections is the advent of the “supermax” prison, of which there are now roughly three dozen in the United States, including New York’s newest facility. A supermax is like a huge SHU, with 100 percent segregation cells. The inmates in them have minimal contact with each other and practically no relationship at all with their guards. “If you ask me, that’s a recipe for a junkyard dog,” an Academy instructor opined to us. I think she was right. And the odd thing is, the idea for a supermax is not new. Solitary confinement around the clock, with idleness during the day: Elam Lynds, before he hit on the congregate system, tried it back in 1821.