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Chicago mobsters of the 1920s have become a sort of "Pirates of the Caribbean" for our city. There are gangster tours, a Tommy Gun's dinner theater, speakeasies that are no longer speakeasies, and we once had a sports team called the Chicago Hitmen. So it's easy to gloss over the fact that these murderous lawbreakers introduced the world to concepts like the drive-by shooting. The Prohibition-era criminal is romanticized in gangster movies and pop music. And, yeah, some of them in hindsight seem particularly silly and curious, despite being evil, with their goofy hats and names like "Willie Potatoes" and "Cockeyed Louie." The Irish North Side Gang and South Side Italian Chicago Outfit waged bloody war on what is now our doorsteps and doughnut shops. Here, we rank the 17 most notorious killers, thieves, bootleggers and, yes, politicians that continue to fascinate us.
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