From bulletproof cars and Tommy guns to bootlegged liquor and mob hits, gangland Chicago was a dangerous place.
In the early 20th century, a number of organized crime figures rose to infamy in the Windy City, providing illegal alcohol during Prohibition, running gambling rackets, operating brothels, and killing anyone who stood in their way of making a profit.
While Al Capone is by far Chicago’s most infamous crime boss, he was far from the only one. In fact, one of Capone’s low-ranking associates, Tony Accardo, eventually became the boss of the Chicago Outfit himself. Nicknamed “Joe Batters” for beating former allies who betrayed Capone to death with a baseball bat, Accardo turned out to be just as intelligent as he was violent.
Unlike Capone, he led the organization for decades and only spent one night in jail.
And organized crime wasn’t the only reason why the streets of Chicago were so dangerous, as it was also the site of infamous bank robber John Dillinger’s final moments.
After stealing, murdering, and escaping prisons throughout the Midwest, Dillinger’s crime spree only ended when he was gunned down by federal agents in front of Chicago’s Biograph Theatre in 1934.
