Theodore "Teddy" Roe was born in Louisiana in August 1898, the son of sharecroppers who later moved to Little Rock, Arkansas. Growing up in the Jim Crow South, young Theodore learned early that the world was stacked against him, but he possessed something that would define his entire life: an unshakeable determination to carve out his own destiny. He developed a skill for sewing after apprenticing under a local tailor and entered the criminal world via bootlegging. His light complexion allowed him certain advantages in a segregated society, but it was his sharp mind and fearless nature that would eventually make him a legend on Chicago's South Side.

By the 1940s, Roe had transformed himself from a small-time bootlegger into an African-American organized crime figure who led an illegal gambling empire in South Side, Chicago. His operation centered on the "policy" game—a numbers racket that had become a vital economic engine in black neighborhoods across the city. But Roe was different from other criminal bosses. He earned the nickname "Robin Hood" because of his philanthropy among the neighborhood poor. Roe is remembered for paying hospital bills for newborns, and funeral tabs for the deceased. When people were cheated by competing gambling operations, they came to Roe for justice, knowing he would make things right. He lived in Chicago with his wife, Carrie, and built a reputation as a man who stood up for his community when few others would.

The end came when Roe refused to bow to the Chicago Outfit's demands for tribute. After refusing to pay "street tax" or hand over his illegal gambling empire to the Chicago Outfit, Roe fatally shot a made man who had been ordered to assassinate him. Though the killing was ruled self-defense, the Italian-American crime syndicate could not let such defiance go unpunished. Roe was murdered in retaliation by the Sicilian-American Outfit crew commanded by caporegime Sam Giancana on August 4, 1952. He was just 53 years old, killed two weeks before his 54th birthday.

Roe was laid out in a casket costing thousands of dollars and received the biggest funeral of any Chicago African American since the boxer Jack Johnson in 1946. Thousands lined the streets to catch a glimpse of Roe's 81-car funeral procession. The massive turnout was a testament to the man who had dared to challenge the established order and had used his criminal enterprise to lift up his community. Theodore "Teddy" Roe died as he had lived—on his own terms, refusing to surrender his dignity or his people's interests to a system designed to crush them both. His story remains a complex legacy of crime and community, of a man who found power in an unjust world and chose to share it with those who had none.