James "Diamond Jim" Colosimo

Jim Colosimo was such a giant in Chicago he needed two nicknames: Big Jim and Diamond Jim. As the owner of Colosimo’s Café, 2160 South Wabash, Colosimo got to know all the city’s celebrities, all of its hoodlums, and a good many of its whores. He was a commanding presence, in his white linen suits and his diamond-studded rings. Before Torrio and Capone, Colosimo was the most powerful figure in the city’s underworld. But when Torrio and Capone began to gain power, Colosimo had to go. Just months after Capone’s arrival in Chicago, in May of 1920, Colosimo was executed: shot behind the ear while standing in his restaurant. The killer or killers—some say Capone was the shooter, some say it was Frankie Yale—got away. The balance of power in Chicago would tilt from that moment on toward Torrio and Capone.

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