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Led by Warden Thomas Mott Osborne, a wave of prison reform at the start of the 1900’s changed much of how Sing Sing Prison operated. After spending a week undercover in Auburn State Prison, Osborne began to develop prison reform ideas that emphasized rehabilitation and self-management for the incarcerated. He sought to promote humane treatment and believed that allowing incarcerated people the ability to develop self-government programs as social education would better their lives both inside and outside of the prison.
With a motto of “Do good; Make good” and a board of elected delegates, The Mutual Welfare League allowed the incarcerated to plan programs to suit their needs and prepare them for release. They had an internal currency and weekly wages which gave the incarcerated the freedom to own things for the first time in the prison’s history. They also had their own court system of punishment for minor offenses that encouraged accountability amongst the prison’s population. Programs were run by committees made up of the incarcerated that included athletics, education, legal, and entertainment. |
Thomas Mott Osborne
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Baseball at Sing Sing Prison
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It’s no surprise that with the prison’s proximity to New York City that many of the incarcerated were baseball fans, and thus baseball became one of the Mutual Welfare League’s biggest successes. Osborne himself stated that “baseball would be the best way of cementing an honor system among the men” and Sing Sing’s teams became widely known outside of prison walls. The Ossining Orioles would go on to play major league teams several times in this era from inside the prison, but no game was as memorable as when the New York Yankees came to Sing Sing Prison.
On September 5, 1929 the Yankees brought their best to the prison for an exhibition game and played for packed bleachers of prison staff and the incarcerated. Since the game was more for entertainment, the team played in their “Babe Ruth Circus style” and ended up signing autographs more than actual ball playing! The Yankees would win 17-3 over the Ossining Orioles and Babe Ruth hit three home runs, including one that’s said to be his longest ever at 620 feet. |
Babe Ruth, 1920
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In 2019, the Sing Sing Prison Museum acquired a baseball signed on that day by the New York Yankees.
