In 1895, Giacomo "Big Jim" Colosimo moved into Chicago's Levee District, home to 2000 brothels, saloons and gambling dens.
Ironically, legitimate work as a street sweeper caused his rise in the underworld, as Colosimo organized the street sweepers into a social club that came to the attention of notorious Aldermen "Bathhouse" John Coughlan and "Hinky Dink" Kenna. Coughlan and Kenna who controlled political graft in the Levee, made Colosimo a precinct captain and a bagman for brothel payoffs.
Colosimo married Victoria Moresco, who owned a second-rate whorehouse, and built it up into a string of brothels, saloons and gambling dens. His prosperity attracted Black Hand extortionists who made death threats against "Big Jim" and his wife. In self-defense, Colosimo hired his nephew, Johnny Torrio, to kill the extortionists. Torrio stayed on to manage Colosimo's empire and helped Big Jim expand outside the Levee, organizing vice districts in Burnham and other Chicago suburbs.
Opening a swank Levee night club called Colosimo's, Big Jim fell in love with Dale Winters, a choir singer turned chorine. He divorced Victoria and began to manage Winter's career. Increasingly he left his underworld business to Torrio.
In 1920, as Prohibition offered criminals new avenues to profit, Colosimo vetoed Torrio's decision to expand their operations into boot-legging.
On May 11, Big Jim walked to the club's front door to meet a whiskey delivery. Two shots rang out, killing him. His murderer was never caught but Torrio's friend Brooklyn gangster Frankie Yale was picked up that night in a police dragnet.
(1992 Max Allan Collins & George Hagenauer)