The Rise and Fall of Teddy Roe: A Chicago Gangster Story

In 1950s Chicago, the Outfit wanted control of the South Side's lucrative policy wheels — the numbers games run by Black bosses for decades. Most of the policy kings gave in. Theodore "Teddy" Roe refused. This documentary tells the story of Teddy Roe: how he became one of the most powerful policy kings on Chicago's South Side, how he stood up to Sam Giancana's mob, the 1951 shootout that left Outfit gunman Leonard "Fat Lenny" Caifano dead, and the ambush that ended Roe's life in 1952. Using newspaper archives, Kefauver Committee testimony and historical accounts, we trace how one man's defiance became a turning point in the history of Black organized crime in Chicago. Subscribe to Bloody Reports for new true crime documentaries every week. #TrueCrime #BlackHistory #ChicagoHistory