Episodes

  • Al Capone All-American: Downfall and the Feds
    Mar 5 2026

    SUBSCRIBE TO THE NEW HOME OF THE OUTFIT ON PATREON! https://www.patreon.com/TheOutfitPod

    Parting is such sweet sorrow, and never more-so than in the season one finale of The Outfit. In the final episode of “Al Capone: All-American,” Al Capone, at the height of his powers, finds himself trapped in a gilded cage — hunted by gangland enemies, the IRS, the President, and a little-known fed named Eliot Ness. And just as we can learn from history on how to launch a podcast on Patreon, Capone's successors learned how best to hang on to the power he lost—a dark lesson still adhered to by the gangsters in power today.

    To keep up with Alana, follow her on Instagram: @alanalevinson

    Sources

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

    Milwaukee PBS Presents "Al Capone: Prohibition and Wisconsin"

    "The O’Hares: A Story Of Redemption Between Father And Son Easy Eddie And Butch O’Hare," Aimee Lamoureux, All That's Interesting

    Get Capone: The Secret Plot That Captured America's Most Wanted Gangster by Jonathan Eig

    Eliot Ness: The Rise and Fall of an American Hero by Douglas Perry

    Scarface and the Untouchable: Al Capone, Eliot Ness and the Battle for Chicago by Max Allan Collins & A. Brad Schwartz

    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 and magazines: The Chicago Tribune, The Daily Worker, Time Magazine, New York Daily News, Chicago Magazine, The New York Times.

    ---

    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.

    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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    1 hr and 2 mins
  • Al Capone All-American: Jake Lingle and the Media
    Feb 26 2026

    When a popular crime reporter for the Chicago Tribune is executed in broad daylight, all eyes turn to Capone. In the penultimate episode of "Al Capone All American," the heat is on, and Dan and Alana find not all is what it appears as the tides change on the public’s perception of our infamous mobster.


    Sources

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

    The great Chicago history site Chicagology (https://chicagology.com/)

    Scarface and the Untouchable: Al Capone, Eliot Ness and the Battle for Chicago by Max Allan Collins & A. Brad Schwartz

    All Things Considered by Howard Vincent O'Brien

    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 and magazines: The Chicago Tribune, The Daily Worker, Time Magazine, New York Daily News, Chicago Magazine.

    ---

    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.

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    57 mins
  • 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.

    Show More Show Less
    1 hr and 6 mins
  • 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.

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    1 hr and 3 mins
  • 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.

    Show More Show Less
    59 mins
  • Al Capone All-American: The North Side Mob
    Jan 29 2026

    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.


    ---

    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.

    Show More Show Less
    1 hr
  • Al Capone All American: Prohibition
    Jan 22 2026

    Description:

    This week, on the next installment of "Al Capone All-American," Dan and Alana turn to the greatest gift Al Capone could have asked for on his 21st birthday: the national prohibition on the sale and manufacture of alcohol. From the Ku Klux Klan, to poisoned rotgut liquor, to the singularly forgotten political genius behind the law, prohibition would come to define an entire era of American history--a story freshly relevant today.


    Sources

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

    The War on Alcohol: Prohibition and the Rise of the American State by Lisa McGirr

    Bootleg: Murder, Moonshine, and the Lawless Years of Prohibition by Karen Blumenthal

    Prohibition: Thirteen Years That Changed America by Edward Behr

    Smashing the Liquor Machine: A Global History of Prohibition by Mark Lawrence Schrad

    One Hundred Percent American: The Rebirth and Decline of the Ku Klux Klan in the 1920s by Thomas R. Pegram

    Prohibition: A Very Short Introduction by W.J. Rorabaugh

    Alcoholics Anonymous

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

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

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

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

    Young Al Capone: The Untold Story of Scarface in New York, 1899-1925 by William and John Balsamo

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

    Capone: The Man and the Era by Laurence Bergreen


    Newspapers and Magazines: The Buffalo News, The Daily Item, the Springfield News-Sun, the Hartford Courant, Los Angeles Times, Washington Daily News, Brooklyn Daily Times, Atlanta Journal-Constitution, New York Daily News, Chicago Tribune.


    ---

    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.

    Show More Show Less
    1 hr and 2 mins
  • Al Capone All-American: Torrio vs Colosimo
    Jan 15 2026

    In this, the second episode of Outfit’s limited series "Al Capone All-American," Dan and Alana learn how the young Scarface, now on the cusp of adulthood, found himself drifting westward toward the city of destiny: Chicago. Under the influence of two underworld mentors with competing philosophies, who will Al Capone align himself with as Prohibition rears its head?


    Sources

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

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

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

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

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

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

    Young Al Capone: The Untold Story of Scarface in New York, 1899-1925 by William and John Balsamo

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

    Capone: The Man and the Era by Laurence Bergreen

    Newspapers including The Brooklyn Daily Times, The New York Daily News, The New York Times, The New York Herald, 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 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.

    Show More Show Less
    52 mins