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Authors: Ted Conover

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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

had become a place where no one had any idea what was supposed to occur … increasingly unmanageable. Senior departmental staff invested negligible effort to correct operational deficiencies at the facility. … In spite of the lack of interest … Ossining continued to function without any “serious” incidents. It had its own way of life which was perceived by many to enable the facility to function in spite of departmental guidelines. Accordingly, senior staff were reluctant to disturb what appeared to be Ossining’s equilibrium.

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:

ALBANY
—Sex, drugs and gambling have been rampant in Sing Sing prison over the last two years under the protection of a clique of rogue correction officers, according to guards and a former ranking prison official.

The sexual escapades in the maximum-security prison
allegedly include trysts between male inmates and female guards—including two suspected of prostitution—in the prison-chapel projection room and a cell.

Guards who tried to crack down on inmate drug use were subject to death threats—purportedly by corrupt officers, according to one guard.

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:

One thing that the judges, policemen, and administrators of prisons seem never to have understood, and for which they certainly do not make any allowances, is that Negro convicts, basically, rather than see themselves as criminals and perpetrators of misdeeds, look upon themselves as prisoners of war, the victims of a vicious, dog-eat-dog social system that is so heinous as to cancel out their own malefactions: in the jungle there is no right or wrong.

Rather than owing and paying a debt to society, Negro prisoners feel that they are being abused, that their imprisonment is simply another form of the oppression which they have known all their lives. Negro inmates feel that they are being robbed, that it is “society” that owes them, that should be paying them, a debt.

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.

To become a good officer requires much more knowledge and experience than is generally supposed; and it is a long
time after a new officer enters upon his duty, before he becomes, even under the most favorable circumstances, fully competent to discharge it. It is not like a man’s driving a herd of oxen or working a piece of machinery, the whole mechanism of which he can learn in a short time. But it is controlling the minds of men, no two of which are alike—it is curbing their tempers, whose manifestations are infinitely various—it is directing their motives which are as diverse as their personal appearance or physical conformation. And it requires an intimate knowledge, if not of human nature at large, at least of the habits, tempers and dispositions of the men immediately under their charge … under such circumstances, the most gifted man would be the better for experience, and the less gifted would be more valuable than him, if he had experience enough.

This consideration, so evidently the dictate of good sense, seems to be entirely overlooked in the government of our prisons, and changes occur, among the officers, from whim, caprice, or political motives, with a frequency that is utterly subversive of good government.

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.

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