August 26, 1898 - Theodore Roe
Roe built and maintained one of the most resilient independent numbers operations in mid-century Chicago, holding his ground in Bronzeville against sustained pressure from the Chicago Outfit at a time when mob consolidation was eliminating rivals across the city. His refusal to capitulate — surviving multiple assassination attempts before finally being killed in 1952 — made him an unusual figure in the organized crime landscape of the era.
From Wikipedia
Theodore L. "Teddy" Roe (August 26, 1898 – August 4, 1952) was a Black American organized crime figure who led an illegal gambling empire in South Side, Chicago during the 1940s and early 1950s. Roe earned the nickname "Robin Hood" because of his philanthropy among the neighborhood poor. 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.
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