Newjack

by Ted Conover

When I got back home after that experience, I went to bed and stayed there for a month. During that month I lost thirty pounds. As soon as I was able to get out of bed, I went to the Adirondacks to recover my strength.

  But a change had come over me. I was oppressed by a feeling of anxiety and menace. I did not realize the trend of my subconscious thoughts until duty took me to the death chamber again and I stood on the edge of the rubber mat, within reach of the chair. On that occasion, just after I had given the signal for the current to be turned on—while the man in the chair was straining against the straps as the load of 2,200 volts shot through his body—I felt for the first time a wild desire to extend my hand and touch him.

  Afterwards I subjected myself to severe self-analysis. I decided that my wild and irrational desire was merely a vagrant impulse, and that it would not occur again. But I was wrong. At each subsequent execution the impulse became stronger. It finally got so compelling that I was forced to grip my fingernails into my palms in order to control it. Each time I had to stand farther and farther from the chair. But even then I would feel a sudden, terrifying urge to rush forward and take hold of the man in the chair, while the current was on.

  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,

  … whether our Prison System is as unintelligent as I think it is; whether it flies in the face of all common sense and all human nature, as I think it does; whether, guided by sympathy and experience, we cannot find something far better to take its place, as I believe we can.

  So, by permission of the authorities and with your help, I am coming here to learn what I can at first hand … I am coming here to live your life; to be housed, clothed, fed, treated in all respects like one of you. I want to see for myself what your life is like, not as viewed from the outside looking in, but from the inside looking out.

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

  Of course I am not so foolish as to think that I can see it from exactly your point of view. Manifestly a man cannot be a real prisoner when he may at any moment let down the bars and walk out; and spending a few hours or days in a cell is quite a different thing from a weary round of weeks, months, years.

  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… .

  I believe every man in this place hates and detests the system under which he lives. He hates it even when he gets along without friction. He hates it because he knows it is bad; for it tends to crush slowly but irresistibly the good in himself.

  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,

  that … the prison warden, to be effective, would have to constitute himself not as an instrument of punishment but a firm, frank friend in need. He would have to stretch humanitarianism to the limits of the law, with a stiff punch always in reserve… . My job is to hold my men and, as far as possible, to win them over to sane, social thinking. And I judge the effectiveness of that job not so much by obedience to rule, for rules can be enforced, but by the humor of the general prison population.

  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 indust
ry 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.

  From my desk within the walls of Sing Sing, I see daily the constantly increasing numbers of boys and young men who are committed to prison. A very great proportion could be made into law-abiding, resourceful citizens… . You may be shocked by their youth, yet they are typical of the small army of young men that make up a major proportion of the population of our prisons… . We have come to the aid of our savings banks, we have organized to save our forests, why haven’t we some plans for youth that will take our young people off the road, that road that leads them, year after year, in a constant procession, to the gates of our prisons …?

  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.