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The Outfit

The Outfit

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Welcome to The Outfit — where each week, a fascinating (and often hilarious) Mafia story reveals something deeper about the way our society works. Hosted by Alana Hope Levinson and Dan O'Sullivan.

From Higher Ground and Headgum

© Higher Ground
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    Épisodes
    • Casino with Demi Adejuyigbe
      Feb 19 2026

      This week, Dan and Alana are joined by Demi Adejuyigbe — writer, comedian, and internet personality — to talk Martin Scorsese’s Casino. From lavish costumes to Oscar snubs, the crew breaks down this classic 1995 film to see how it measures up against the mob movie hall of fame.


      Check out Demi's stand-up special on Dropout


      ---

      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 CJ Archerd and Franchesca Diaz

      Sound Design and Engineering by Ryan Kozlowski and Andrew Eapen

      Show theme is Bittersweet Defeat by OTE


      Like 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.

      Afficher plus Afficher moins
      1 h et 6 min
    • Al Capone All-American: The St. Valentine's Day Massacre
      Feb 12 2026

      February 14th, 1929: a routine police raid on a Chicago garage turns out to be anything but, as seven men are machine-gunned to death; an event colloquially known as the St. Valentine’s Day Massacre. In this episode of “Al Capone All-American,” love is NOT in the air, as Dan and Alana find that the dead men are but collateral damage to an insidious gang war gripping the streets of Chicago—and all signs point to one Al Capone.


      Sources

      A special debt of gratitude to William J. Helmer & Arthur Bilek, authors of The St. Valentine's Day Massacre: The Untold Story of the Gangland Bloodbath that Brought Down Al Capone--the book which solved the case. A special thank you as well to William J. Helmer for his role in publishing Georgette Winkler's Al Capone and His American Boys: Memoirs of a Mobster's Wife, the most important account of the slayings.


      Historian Mario Gomes's excellent website, My Al Capone Museum (https://www.myalcaponemuseum.com/)


      Capone: The Man and the Era by Laurence Bergreen

      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

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

      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

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

      Newspapers including The Chicago Tribune, The Chicago Daily-News, The Chicago American.

      ---

      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

      See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

      Afficher plus Afficher moins
      1 h et 3 min
    • Al Capone All-American: Cicero & Politics
      Feb 5 2026

      As a wave of political unrest sweeps 1923 Chicago, along comes the rise of a progressive mayoral candidate who vows to take down the bootleggers, effectively driving Al Capone’s operation to the suburb of Cicero, Illinois. In this week’s installment of “Al Capone All-American,” Dan and Alana find the Outfit’s bloody assault on democracy in Cicero is but a prelude for their return to Chicago—installing a buffoonish new mayor all-too reminiscent of a current-day executive.


      Sources

      Historian Mario Gomes's excellent website, My Al Capone Museum (https://www.myalcaponemuseum.com/)

      Capone: The Man and the Era by Laurence Bergreen

      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

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

      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

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

      The Chicago Historical Homicide Project, Northwestern University.

      "The Mostly True Story of America’s First Black Private Investigator," Matthew Wolfe, The Atavist Magazine.

      Newspapers & magazines including: The Chicago Defender, Time Magazine, The Daily Worker, The Chicago Daily News, The Chicago Tribune, Chicago Record-Herald, The Chicago Sun-Times, The Inter Ocean.

      ---

      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


      Like 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.

      Afficher plus Afficher moins
      59 min
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