In 2014, as New York State’s prison population declined, state officials shuttered Mount McGregor. This medium-security correctional facility had a long history of creative rehabilitation. In the 1910s, it was a sanitarium for tubercular patients. After WWII, it welcomed convalescing veterans. In 1982, now a prison, it developed the state’s first Alcohol and Substance Abuse Treatment program. As the War on Drugs increased prison populations in the 1980s, and state politicians cut funding for carceral programs in the 1990s, teachers, counselors, and prisoners themselves empowered incarcerated men to change their lives. Programs provided incarcerated men with support to survive and thrive; ironically, many lost access to such support upon release. Mount McGregor’s closing raises questions about what prisons are for, how to treat people who remain locked up in an age of decarceration, and how to address economic in equality, racism, and other factors that condition prisoners and their communities.