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Al Capone’s Bloody Business | Chicago Stories

Al Capone’s Bloody Business

During the Prohibition-era 1920s, a young man named Al Capone succeeded his mentor, Johnny Torrio, to run the Chicago Outfit. An Italian-American crime syndicate first established by “Big Jim” Colosimo at the turn of the century, the Outfit amassed an estimated $100 million in revenue – more than $1.5 billion today – through its nearly 200 brothels, illegal alcohol production and sales, gambling, and racketeering. For several years, the mob had a chokehold on Chicago politics, influencing elections through intimidation and violence and working in cahoots with the aldermen who ran the city’s political machine. This quintessentially Chicago story traces the powerful criminal enterprise from its inception through its 1920s heyday and to its gradual demise. At the center of it all, wearing a sleek fedora and a knowing smirk, was Capone – “Public Enemy No. 1” – and one of America’s most notorious gangsters.

The age of jazz and speakeasies, shorter hemlines, and bigger parties was also a time of gangland violence in 1920s and ’30s Chicago. As the infamous Al Capone took over as the boss of a major South Side gang, a series of violent mob disputes called the Beer Wars erupted. Hundreds of gangsters were killed as Al Capone’s mob, the North Side gang, and various other groups fought over money, territory, and control over bootlegging operations. In the end, the Chicago Outfit emerged as ... Read more

Extended Interview: Dave Jemilo, Owner of The Green Mill

Dave Jemilo, owner of The Green Mill, shares the lore behind the famous cocktail bar Al Capone once frequented.

He was sometimes called “Scarface.” He was declared “Public Enemy No. 1” in 1930. And he was one of the most formidable and famous gangsters in American history. With a fedora tipped casually to the side, an elegant suit, and a cigar sometimes tucked between his teeth, Al Capone was the epitome of the organized-crime boss. “Al Capone is the prototypical celebrity gangster,” historian Clarence Goodman told Chicago Stories. “He set the standard by which every other gangster who has his or her picture in the newspaper is judged.” Although he eluded legal consequences for bootlegging and murder for years, Capone’s downfall would come in the form ... Read more

You’ve got your Jimmys. You’ve got some Johnnys. And then you’ve got men like “Greasy Thumb” or “Hinky Dink.” In the 1920s gangster scene, Chicago was full of interesting and dangerous characters and even more interesting nicknames. Sometimes, nicknames were used to conceal the identities of gangsters from the authorities – or anyone else who may have wanted to whack a fella. See if you can guess the nickname that belongs to each mobster or gang associate featured in the show. You can practically hear the brassy jazz and smashing beer bottles... Read more

What is now a parking lot adjacent to a senior living center on Clark Street in Lincoln Park was once the location of a shocking, violent event at the height of Chicago’s gangland wars of the 1920s. The St. Valentine’s Day Massacre marked a critical point in the Beer Wars, a years-long conflict between Chicago’s gangs who were battling for control of the bootlegging market and organized crime during Prohibition. On February 14, 1929, six men associated with George “Bugs” Moran’s North Side gang were in a garage on Clark Street... Read more

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Lead support for Chicago Stories is provided by The Negaunee Foundation.

Major support is provided by Gwen Cohen and the TAWANI Foundation.

Funding for Chicago Stories: Al Capone’s Bloody Business is provided by Clifford Law Offices, and Mr. and Mrs. Robert Shaw.