Sing Sing Correctional Facility: A Shift to More Humane Practices

By Molly Osborn

As one of New York’s oldest prisons, picturesquely situated overlooking the Hudson River, Sing Sing Correctional Facility marks an important part of the Hudson Valley’s history. From the time the facility was first established in 1826 to its present-day operation, Sing Sing’s policies and practices have progressed significantly, shifting from horrible treatment of its prisoners with the use of capital punishment to more humane practices, focusing on the reformative aspects of prison. This shift in policies began in 1914 primarily due to the influence of wardens Thomas Mott Osborne and Lewis E. Lawes.

By the early nineteenth century New York City’s jail had become overcrowded and the demand arose for a new state prison. Due to this demand, the governor of New York formed a commission in 1824 in charge of creating a new facility (Lawes 1933, 7).

(Blumenthal 2004, 264)

(Blumenthal 2004, 264)

This commission ultimately decided to build a prison on the current site of Sing Sing because of the natural resources available there. Sing Sing—aptly named after “Sint Sinck,” the Native American words for “stone upon stone”—was built upon a quarry. Prisoners from Auburn Prison in upstate New York were shipped in by way of the Erie Canal to work the marble and use the raw materials to build the original structure of Sing Sing (Blumenthal 2004, 3-11). Since that time, when the prison could only accommodate 800 prisoners, Sing Sing has grown significantly and now includes several different buildings.

From the time when Sing Sing officially opened in 1826 to the early 1900s its prisoners suffered through atrocious living conditions. Warden Thomas Mott Osborne who briefly served as the Sing Sing warden from 1914 to 1916 stated that when he arrived at the prison, the prisoners’ living conditions were “unspeakably bad…To call them unfit for human habitation [was] to give them undeserved dignity. They [were] unfit for pigs” (Blumenthal 2004, 3-5). Their cells were extremely cramped, at only 3 feet by 7 feet, and sometimes two prisoners had to occupy the same tiny cell (Conover 2001, 3). In addition to the lack of space, prisoners suffered from a lack of indoor plumbing or central heating as well as limited natural light and airflow (Tannenbaum 1933, 326-329).

Outraged by the horrible conditions in American prisons, New York politician Thomas Mott Osborne began working toward prison reform in the early twentieth century. In 1913, New York governor William Sulzer appointed Osborne as chairman to the New York State Prison Reform Commission. Starting at Auburn prison in upstate New York in 1913, Osborne published a book describing his experience at Auburn when he chose to live as incarcerated men did for six days to better understand the prisoners’ living conditions. Later that year, Osborne was hired as the warden of Sing Sing, where he worked for almost two years before resigning (Tannenbaum 1933, 100). During his time as warden, Osborne significantly improved the conditions for prisoners. He implemented the Mutual Welfare League, made up of Sing Sing inmates, to provide prisoners with entertainment including sports and leisure activities, like swimming. The Mutual Welfare League was also in charge of disciplining prisoners for minor offenses (Blumenthal 2004, 54).  This new disciplinary system contributed to the idea that the prison should be a community with the prisoners taking part in managing their own lives—an idea that Osborne worked very hard to implement.

In addition to allowing prisoners to contribute to their own disciplinary policies, Osborne also wanted to equip his prisoners with the skills necessary to survive once they left Sing Sing. Osborne employed a Sing Sing economic system, using a currency produced and distributed by the league. He wanted to prepare prisoners for the outside world and included other real-world elements into their prison life, including weekly wages that would pay for their meals, rent and insurance policies (Blumenthal 2004, 54).

After Osborne chose to leave Sing Sing, five different men served as warden over the course of three years before Lewis Lawes, coming from working at the New York

(Lawes 1933, 1)

(Lawes 1933, 1)

Reformatory at New Hampton, signed on (Lawes 1932, 64). Continuing and developing Osborne’s ideals of community and reformation, Lawes improved the policies at Sing Sing, working toward a more humane treatment of its prisoners. Lawes provided prisoners with numerous recreational activities, including Sing Sing’s famous baseball and football teams that drew spectators from the surrounding area. Each prisoner had access to a library and were given some solitary free time toward the end of the day in which “the prisoner [did] his letter writing, reading, studying—and reflecting (Lawes 1933, 15)” Lawes even

allowed prisoners to read the newspaper and listen to the radio, in order to stay connected to the outside world. Whereas Sing Sing’s meals during the nineteenth to early twentieth centuries had been bland and repetitive, according to Lawes, “the meals are varied so as to provide a balanced diet and there is always enough for even the hungriest” (Lawes 1933, 16).

(Blumenthal 2004, 117)

(Blumenthal 2004, 117)

Besides accommodating simple entertainment and living needs, Lawes provided for prisoners’ social and economic needs as well. After a brief “reception” period upon entering Sing Sing, Lawes allowed his prisoners to wear white button-down shirts and black ties, instead of the common prison jumpsuits. He also provided all of the prisoners with an education to make sure that every man had at least the same level of schooling as a sixth grade grammar student (Lawes 1933, 12). He wanted the prisoners to look and act in a professional manner, learning how to dress and conduct themselves once they were released from prison. Upon their release, Lawes even supplied each man with 20 dollars in addition to whatever extra money he had earned during his sentence, “a suit, shoes, underwear, sox, hat, and an overcoat (in winter); and a railroad ticket to the city or town from which he was sentenced”(Lawes 1933, 19). Lawes did everything in his power to reform the prisoners of Sing Sing and give them a chance to better themselves and start over.

Even after Lawes retired in 1941, Sing Sing continued to operate on his principles of humane treatment. In 1951, discharged prisoner Edward Kelly wrote a letter to the current warden saying:

“Due to the fact that I’m leaving the ‘Death House,’ I cannot say I have any regrets, nor will I recommend it to anyone, but I can inform them that, if they are ever unfortunate enough to go to Sing Sing, they will be very well treated. I had no fault to find with anything or anybody during my stay, every reasonable request was granted. The entire staff of the prison are a credit to New York State. The Officers and Guards are as fine a group of men as you could find anywhere” (Christianson 2000, 51).

Sing Sing, despite being a structure of forced confinement, provided—and continues to provide—its prisoners with the fairest treatment possible. Due to Lawes’s drastic improvements at Sing Sing, the prison remains permanently changed for the better. Today, Sing Sing Correctional Facility functions as a maximum security prison and continues to improve its policies. Now housing over 2,000 prisoners, Sing Sing has discontinued its use of the electric chair as capital punishment due to a change in state policy, added a Special Needs Unit to treat prisoners with the HIV-AIDS virus, and provides more advanced academic and vocational educational programs to its inmates (Brian 2005, 201). While improvements can always be made, Sing Sing has progressed immensely from its initial conditions in 1825 largely thanks to the reform efforts of both Thomas Mott Osborne and Lewis E. Lawes.



Blumenthal, Ralph. 2004. Miracle at Sing Sing: How one man transformed the lives of America’s most dangerous prisoners. New York: St. Martin’s Press.

Brian, Denis. 2005. Sing Sing: The Inside Story of a Notorious Prison. Prometheus Books. eBook.

Christianson, Scott. 2000. Condemned: Inside the Sing Sing Death House. New York: New York University Press.

Conover, Ted. 2001. Newjack: Guarding Sing Sing. New York : Vintage Books.

Lawes, Lewis E. 1933. Sing Sing. New York: Strawberry-Hill Press Inc.

Lawes, Lewis E. 1932. Twenty Thousand Years in Sing Sing. New York, R. Long & R. R. Smith, inc.

Tannenbaum, Frank. 1933. Osborne of Sing Sing. Chapel Hill: The University of North Carolina press.

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