Andy Craig's Life of Crime

Between 1880 and 1925, Andy Craig was consistently at the center of Chicago's underworld. While he owned many saloons, brothels, and gambling dens over the years, his most famous hang-out was the Tivoli, located at 383 S. State St. (in today's street numbering system, this would be 645 S. State), in the middle of this parking lot by the elevated tracks. The Tivoli was in operation between 1898 and 1903.

The Tivoli was known as the meeting place for most of the South side's pickpocket crew. In return for spending their money on the Tivoli's amenities, which besides the saloon included a sports book in the basement and prostitutes upstairs, Andy Craig served as the general bail bondsman for the group, always ready with a loan when one of them ended up in the Harrison Street police station. It was said that Craig, who became known as the "bail bond king", could be found serving bail at the police station every single day in the year, and for this reason the patrolmen came to refer to pickpockets as "Craig's people."

The Mayor ordered the Tivoli closed in 1903, after a sweep on Thanksgiving Day morning found the saloon open at 1:15 a.m., well past the midnight closing hour. The Tribune described the Tivoli at that time as home to all type of "disreputable persons," including "pickpockets, thieves, women, confidence men, and other law breakers." Not just thieves, but women!

This did not end Craig's career. Like hundreds of other Custom House Place and Whisky Row residents also swept out of business in 1903 by popular demand, he moved his operations south to the new Levee district centered around 22nd and Dearborn Streets, and continued operating as a pander, loan shark, saloon-keeper, and bookie for the rest of his life. Newspaper articles as late as 1925 name the old-time saloon keeper as a material witness in a case in which he loaned $2,500 to a known heroin addict, as the owner of the Northern Lights Cafe at Devon and Broadway, where a policeman shot a gangster in a firefight, and as a well-known book-maker operating out of Capone's Hawthorne Race Track.