Lynds spent months researching possible locations for the prison, considering Staten Island, the Bronx, and Silver Mine Farm, an area in the town of Mount Pleasant on the banks of the Hudson River.

[10] Lynds selected 100 inmates from the Auburn prison for transfer and had them transported by barge via the Erie Canal and down the Hudson River to freighters.

On their arrival on May 14, the site was "without a place to receive them or a wall to enclose them"; "temporary barracks, a cook house, carpenter and blacksmith's shops" were rushed to completion.

Luckey also created a religious library in the prison, with the purpose of teaching correct moral principles.

[16] She overturned the strictly silent practice in prison and introduced social engagement to shift concern more toward the future instead of dwelling on the criminal past.

One of them conspired with powerful political allies to destroy Osborne's reputation, even succeeding in getting him indicted for a variety of crimes and maladministration.

[23] While warden, Lawes brought about reforms and turned what was described as an "old hellhole" into a modern prison with sports teams, educational programs, new methods of discipline, and more.

High-profile executions in Sing Sing's electric chair, nicknamed "Old Sparky", include Julius and Ethel Rosenberg on June 19, 1953, for espionage for the Soviet Union on nuclear weapon research; and Gerhard Puff on August 12, 1954, for the murder of an FBI agent.

In 1972, the United States Supreme Court ruled in Furman v. Georgia that the death penalty was unconstitutional if its application was inconsistent and arbitrary.

In the early 1970s, the electric chair was moved to Green Haven Correctional Facility in working condition, but was never used again.

[34] In 2013, Sing Sing Superintendent Michael Capra and NBC producer Dan Slepian worked with a group of 12 incarcerated men to start a program called "Voices From Within", created by Jon-Adrian Velazquez in an effort to "redefine what it means to pay a debt to society"[35] Their first project was an emotional video about gun violence, where the men spoke directly to the youth in the communities from which they came.

[39] Its impact on social and institutional behavior was formally evaluated by the John Jay College for Criminal Justice, in collaboration with the NY State Department of Corrections.

[42] The organization Hudson Link for Higher Education in Prison provides college courses to incarcerated people to help reduce recidivism and poverty and strengthen families and communities.

In 1998, as part of the get-tough-on-crime campaign, state and federal funding for college programs inside the prison was stopped.

In 1932, "graduate" Jumbo Morano was signed by the Giants and played for the Paterson Nighthawks of the Eastern Football League.

In 1934, State Commissioner of Correction, Walter N. Thayer banned the advertising of activities at the prison, including football games.

These funds had been paying for disbursements to prisoners' families, especially the kin of those executed, and for equipment and coaches' salaries.