In 2001, Caldwood was awarded the Commissioner's Award for Bravery.
In 2016. Caldwood was awarded the NYC Dept. of Correction Guardian Association Medal of Honor, Valor & Merit
Roy and his wife Muriel
In February, 1972, Roy J. Caldwood was a prisoner in the Riker Island Adolescent Remand Shelter, but he wasn’t a criminal. Instead, the assistant deputy warden was a hostage during one of Rikers Island’s frequent riots.
It wasn’t the first time Caldwood faced a riot. In his twenty-year career with New York City’s Department of Corrections 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 for major entertainers to visit and perform for inmates.
Caldwood survived—even thrived—in his dangerous job by learning from his mistakes and moving on, while treating inmates and prison personnel alike with respect. He didn’t always make the right moves, but he tried. And in doing so, he navigated one of the most dangerous prisons in America.
A former World War II US Army “buffalo soldier” Roy J. Caldwood served in the 92nd Infantry Division before spending over twenty-one years (1955-1976) maintaining calm and order in New York City’s prison system.
Starting as a raw recruit, Caldwood rose to the rank of assistant deputy warden on Rikers Island, honing and perfecting a caring, humanistic style that other officers, wardens, and commissioners eventually embraced as the most effective way to treat inmates.
In the words of former Commissioner Jackie McMickens, Caldwood tried to make jail “more livable” for inmates with a combination of respect and smooth institutional operations. Caldwood shared his methods with officer candidates as a lecturer at the Correction Officers Training Academy.
Caldwood’s respectful treatment of inmates helped him safely negotiate non-violent solutions to hostage takings, including his own time as a hostage during the 1972 Rikers Island Riot.