"Big Jim" Colosimo was Chicago’s first "big-time" gang boss. Rising up from being a street-sweeper and 1st ward bagman who knocked out slow-paying madams with brass knuckles, Colosimo married a madam and together they soon acquired ownership of 100 saloons and brothels in Chicago’s infamous red-light district known as the Levee. It was a 16-bock area in Chicago’s 1st Ward which contained virtually all of Chicago’s vice at the beginning of the 20th century including: prostitution, homosexuality, gambling, voodoo, sex circuses, obscene magazines, peep shows, slave auctions, and opium dens in a single area. Over 5,000 prostitutes worked in the Levee, accompanied by homosexual hustlers, pimps, white slaves, dope peddlers, murderers and kidnappers for hire, pickpockets, stick-up men, and burglars. Life was cheap in the Levee and one never knew if the person standing next to him was a bum, drug addict, murderer, pimp, or industrial tycoon or, in a moment of bad luck or carelessness ,if he would be the next to be robbed, beaten or murdered.Colosimo made the mistake of marrying a 19-year-old singer and settling down to live the good life. However, in neglecting his criminal empire, he had signed his own death warrant. In mob parlance, "he had gotten soft." Two weeks after he was married, he was gunned down in his own restaurant. So ended the life of the gangster who created the Outfit which Al Capone was to use in his conquest of Chicago.
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