In February, 1972, Roy J. Caldwood was a prisoner at the Rikers Island Adolescent Remand Shelter, but he wasn't a criminal. Instead, the assistant deputy warden was a hostage during one of Rikers Island's infamous riots.

It wasn't the first time Caldwood faced a riot. In his twenty-one year career with New York City's Department of Correction he helped prevent stabbings from escalating, negotiated with rioting inmates, and foiled an escape attempt from maximum security. He helped prisoners air legitimate grievances, successfully oversaw the Black Panther inmate population, and arranged...