About this episode

The episode explores the violent territorial conflicts between Al Capone's gang and the North Side Mob during Prohibition-era Chicago.

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…

People in this episode

Hosts: Dan O’Sullivan, Alana Hope Levinson

Topics covered

• Prohibition
• Chicago
• organized crime
• mob history
• territorial conflict

Keywords

• Al Capone
• Prohibition
• North Side Mob
• Chicago
• organized crime
• gang wars
• John Torrio
• Bugs Moran

Mentioned in this episode

Organizations: Higher Ground, Headgum, The Daily Worker, The Chicago Daily News, The Chicago Tribune, Chicago Record-Herald, The Chicago Sun-Times

Books & works: The Man Who Got Away: The Bugs Moran Story, The Wicked City: Chicago From Kenna to Capone, Al Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition, Gangland Chicago: Criminality and Lawlessness in the Windy City, Prohibition Gangsters: The Rise and Fall of a Bad Generation, Al Capone: His Life, Legacy, and Legend, The Outfit: The Role of Chicago's Underworld in the Shaping of Modern America, Mr. Capone: The Real - and Complete - Story of Al Capone, Capone: The Life and World of Al Capone, Capone: The Man and the Era

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• Al Capone All-American: Downfall and the Feds · March 5, 2026 · 1h 2m
• Al Capone All-American: Jake Lingle and the Media · February 26, 2026 · 57 min
• Casino with Demi Adejuyigbe · February 19, 2026 · 1h 6m
• Al Capone All-American: The St. Valentine's Day Massacre · February 12, 2026 · 1h 3m
• Al Capone All-American: Cicero & Politics · February 5, 2026 · 59 min
• Al Capone All American: Prohibition · January 22, 2026 · 1h 2m

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