Chicago’s Mob History

Al Capone in 1930.

Al Capone in 1930; the Original Scarface.

The “vicious gangster with the heart of gold” is an old Chicago tradition that still fuels the city’s love/hate relationship with its celebrity gangsters.

Chicago’s first celebrity gangster, Al Capone, the original Scarface, was just 26-years-old when he ran a vice dynasty that included nightclubs, racetracks breweries and brothels in the 1920s. Capone strolled his Cicero neighborhood clad in zoot suits, a cocaine white Fedora hat and an 11.5-carat diamond pinky ring. Capone was the go-to guy if you were poor, down on your luck or in need of a coat for the winter. He partied with the jazz musicians and sent flowers to their mothers. Capone also opened several of the first soup kitchens during the Great Depression; it was his generosity with the common folk that earned him the reputation of Robin Hood. The proud peacock was also a cold-blooded killer, and had personally killed a dozen people and ordered hits on dozens more.  Scarface did not leave this world in a hail of bullets, he was jailed for tax evasion and died of syphilis.

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Deputy Editor, Rolling Out

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