Big Jim Colosimo (the epithet “Big” was applied liberally in the city of broad shoulders) set the pattern for a generation of Chicago gangsters. Flashing diamonds and thousand-dollar bills, Colosimo reigned as lord of the city’s vice and gambling for the first twenty years of the century. He struck bargains with politicians. His patrons at City Hall, the aldermen Michael (“Hinky Dink”) Kenna and “Bathhouse” John Coughlin, were paragons of improbity in a venal city.

The prostitution and gambling from which Colosimo derived his living flourished in the Levee district, from Twenty-second to Eighteenth streets, between Clark and Wabash. There he operated Colosimo’s Café, a pleasure palace opened in 1910 at 2126 South Wabash. Chicago’s high society flocked down from Lake Shore Drive to enjoy the club’s baroque extravagance and to hear Sophie Tucker sing “Angle Worm Wriggle,” a song so suggestive it once got her arrested.

Nothing remains of the hundreds of saloons, gambling dens, and vice parlors that once lit up the Levee. The area, just south of the downtown Loop, is a collection of warehouses, vacant lots, and streets suffering from clinical depression. But the visitor can imagine some of Big Jim’s empire. The legendary Everleigh Club, a brothel at 2131 South Dearborn operated by two sisters from Omaha, was perhaps the most elegant bawdy house in the world. There a perfume machine prettied the air, gold cuspidors awaited patrons’ expectorations, and all the trappings of high society attended the liaisons.