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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.