Al Capone All-American: The North Side Mob episode artwork

EPISODE · Jan 29, 2026 · 1H

Al Capone All-American: The North Side Mob

from The Outfit

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.SourcesThe Man Who Got Away: The Bugs Moran Story by Rose KeefeThe Wicked City: Chicago From Kenna to Capone by Curt Johnson with R. Craig SautterAl Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition by John BinderGangland Chicago: Criminality and Lawlessness in the Windy City by Richard C. LindbergProhibition Gangsters: The Rise and Fall of a Bad Generation by Marc MappenAl Capone: His Life, Legacy, and Legend by Deirdre BairThe Outfit: The Role of Chicago's Underworld in the Shaping of Modern America by Gus RussoMr. Capone: The Real - and Complete - Story of Al Capone, by Robert J. SchoenbergCapone: The Life and World of Al Capone by John KoblerCapone: The Man and the Era by Laurence BergreenNewspapers including The Daily Worker, The Chicago Daily News, The Chicago Tribune, Chicago Record-Herald, The Chicago Sun-Times.---The Outfit is a production of Higher Ground and Headgum.Hosted by Dan O’Sullivan and Alana Hope LevinsonExecutive Produced by Dan O’Sullivan and Alana Hope LevinsonProduced by Julia MurrayProduction Assistance by Franchesca Diaz and CJ ArcherdSound Design and Engineering by Ryan Kozlowski and Andrew EapenShow theme is Bittersweet Defeat by OTELike the show? Rate The Outfit on Spotify and Apple Podcasts and leave a review.Follow Headgum on Twitter, Instagram, and Tiktok. Advertise on The Outfit via Gumball.fmSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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.SourcesThe Man Who Got Away: The Bugs Moran Story by Rose KeefeThe Wicked City: Chicago From Kenna to Capone by Curt Johnson with R. Craig SautterAl Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition by John BinderGangland Chicago: Criminality and Lawlessness in the Windy City by Richard C. LindbergProhibition Gangsters: The Rise and Fall of a Bad Generation by Marc MappenAl Capone: His Life, Legacy, and Legend by Deirdre BairThe Outfit: The Role of Chicago's Underworld in the Shaping of Modern America by Gus RussoMr. Capone: The Real - and Complete - Story of Al Capone, by Robert J. SchoenbergCapone: The Life and World of Al Capone by John KoblerCapone: The Man and the Era by Laurence BergreenNewspapers including The Daily Worker, The Chicago Daily News, The Chicago Tribune, Chicago Record-Herald, The Chicago Sun-Times.---The Outfit is a production of Higher Ground and Headgum.Hosted by Dan O’Sullivan and Alana Hope LevinsonExecutive Produced by Dan O’Sullivan and Alana Hope LevinsonProduced by Julia MurrayProduction Assistance by Franchesca Diaz and CJ ArcherdSound Design and Engineering by Ryan Kozlowski and Andrew EapenShow theme is Bittersweet Defeat by OTELike the show? Rate The Outfit on Spotify and Apple Podcasts and leave a review.Follow Headgum on Twitter, Instagram, and Tiktok. Advertise on The Outfit via Gumball.fm See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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This episode was published on January 29, 2026.

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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...

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