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January 29, 2026 60 mins

It’s prohibition-era Chicago, and Al Capone and his gang boss, John Torrio, stand to make millions off of bootlegging. As long as crime can be organized along professional boundaries, there should be no need for violence. So why, as Prohibition wore on, did things get bloodier and bloodier? This week, Dan and Alana dig into The North Side Mob, and how their uniquely divided power structure led to an increasingly violent fight for territory.


Sources

The Man Who Got Away: The Bugs Moran Story by Rose Keefe

The Wicked City: Chicago From Kenna to Capone by Curt Johnson with R. Craig Sautter

Al Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition by John Binder

Gangland Chicago: Criminality and Lawlessness in the Windy City by Richard C. Lindberg

Prohibition Gangsters: The Rise and Fall of a Bad Generation by Marc Mappen

Al Capone: His Life, Legacy, and Legend by Deirdre Bair

The Outfit: The Role of Chicago's Underworld in the Shaping of Modern America by Gus Russo

Mr. Capone: The Real - and Complete - Story of Al Capone, by Robert J. Schoenberg

Capone: The Life and World of Al Capone by John Kobler

Capone: The Man and the Era by Laurence Bergreen

Newspapers including The Daily Worker, The Chicago Daily News, The Chicago Tribune, Chicago Record-Herald, The Chicago Sun-Times.


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The Outfit is a production of Higher Ground and Headgum.

Hosted by Dan O’Sullivan and Alana Hope Levinson

Executive Produced by Dan O’Sullivan and Alana Hope Levinson

Produced by Julia Murray

Production Assistance by Franchesca Diaz and CJ Archerd

Sound Design and Engineering by Ryan Kozlowski and Andrew Eapen

Show theme is Bittersweet Defeat by OTE


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