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Authors: Ted Conover

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The progress of mankind from physical force to the substitution of moral power in the art and science of government in general, is but very slow, but in none of its branches has this progress, which alone affords the standard by which we can judge of the civil development of a society, been more retarded than in the organization and discipline of prisons …

—Francis Lieber, translator’s introduction to Alexis de Tocqueville and Gustave de Beaumont,
On the Penitentiary System in the United States and Its Application to France
, 1833

Y
ou 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:

From this experiment results the very reverse of those which had been anticipated, was produced; five of those who had been subjected to this confinement, died within a
year, one of them had become insane, and another, watching an opportunity when his keeper brought him something, precipitated himself [jumped] from the gallery … the rest fell into a state of such deep depression, that their lives must have been sacrificed, had they remained longer in this situation.

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,

One cannot see the prison of Sing-Sing and the system of labour which is there established without being struck by astonishment and fear. Although the discipline is perfect, one feels that it rests on fragile foundations: it is due to a
tour de force
which is reborn unceasingly and which has to be reproduced each day, under penalty of compromising the whole system of discipline. The safety of the keepers is constantly menaced. In the presence of such dangers, avoided with such skill but with difficulty, it seems to us impossible not to fear some sort of catastrophe in the future.

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.

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