About Roy

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.

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 

In  February, 1972, Roy J. Caldwood was a prisoner in 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  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.