Episodios

  • Martin Cahill: "The General" & Ireland's Underworld
    Nov 13 2025

    On this episode, Dan travels back to the auld sod to regale Alana with the story of a vicious crime lord with two wives and a weakness for desserts: Martin "The General" Cahill. A product of the Dublin slums and upwardly mobile gangster, Cahill’s rise and fall is a dark reflection of Ireland’s own turbulent history.

    Sources:

    We Don't Know Ourselves: A Personal History of Modern Ireland by Fintan O'Toole

    The General and Evil Empire: The Irish Mob and the Execution of Journalist Veronica Guerin by Paul Williams

    A Secret History of the IRA by Ed Moloney

    Newspapers and Magazines: Hot Press, Dublin Evening Herald, Irish Independent, Sunday Independent, The Star (Dublin).

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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


    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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    1 h y 3 m
  • Charles Becker: The NYPD's Killer Cop
    Nov 6 2025

    1912, Ragtime-era New York. NYPD Lieutenant Charles Becker, celebrity cop, stands accused of a shocking crime: orchestrating the murder of gambler Herman Rosenthal, whose squealing to the press threatened to expose systemic police corruption. In this week's episode, Dan and Alana weigh the evidence in the case of one of the few NYPD officers to ever take a trip to death row.

    Sources:

    Satan's Circus Murder, Vice, Police Corruption, and New York's Trial of the Century by Mike Dash

    The Execution of Officer Becker: The Murder of a Gambler, The Trial of a Cop, and the Birth of Organized Crime by Stanley Cohen

    The Becker Scandal: A Time Remembered by Vina Delmar

    The Bowery Boys, “Case Files of the New York Police Department 1800-1915” podcast episode

    Newspapers and magazines: American Heritage, Crime Magazine, New York Sun, The New York Times, New York Evening World, New York Tribune.

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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


    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.

    Más Menos
    1 h y 3 m
  • A Very Sopranos Halloween with Jesse Farrar
    Oct 30 2025

    Happy Halloween! This week on a spooktacular edition of The Outfit, Dan is joined by longtime friend, host of Your Kickstarter Sucks, Jesse Farrar, for a Sopranos-style therapy session with Dr. Alana. After failing to make headway, the gang takes a deep dive into the pilot of the greatest show of all time, The Sopranos. If you haven't finished the series, listen...if you dare. From Shrek to cannoli to the headaches of owning a driveway, the group breaks down a show even more relevant today than when it came out.



    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

    Managing Producer is Tiffany Hammond

    Sound Design and Engineering by Ryan Kozlowski and Andrew Eapen


    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.

    Más Menos
    51 m
  • Mob Wives: Behind Every Great Mobster...
    Oct 23 2025

    For the Outfit’s very first guest episode, Dan and Alana are joined by Rachel Fisher, co-host of Hollywood Crime Scene, to dive deep into the 2010s reality TV scene. They talk, of course, of VH1’s Mob Wives. In a podcast rife with men in the mob, this week Alana takes the reins for this specialty detour into the lives of the mobsters' wives.


    ---


    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.

    Más Menos
    1 h y 6 m
  • Sammy Gravano: The Rat King
    Oct 16 2025

    After ratting out the Gambino Family and skating away on 19 murders, Sammy “The Bull” Gravano takes a cushy deal and settles down with his family in Arizona. But as Dan and Alana learn in this episode, for a mob snitch on the run, a new lease on life is its own purgatory—and the desert rave scene, an unlikely new kingdom.


    Sources:

    The Arizona Republic, Arizona Daily Sun, Phoenix New Times, Tucson Citizen, The New York Times, UPI, Arizona State Press, CBN, The Smoking Gun, Cosa Nostra News, Crime Library, Arizona Daily Star, Midland Daily News, Reddit, New York Post, New York Daily News, Newsday.

    National Geographic's Narco Wars -- Season 2, Episode 4, "The Mob: How E Busted the Bull"

    Underboss: Sammy "The Bull" Gravano's Story of Life in the Mafia by Peter Maas

    OfficialSammyTheBull on YouTube

    ShaunAttwoodOFFICIAL on YouTube

    MOBFAX on YouTube

    Dateline NBC, April 8, 1997 -- "Raging Bull"

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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 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.

    Más Menos
    55 m
  • Willie Bioff: Labor Racketeering in Hollywood's Golden Age
    Oct 9 2025

    This week on the Outfit, we head to La La Land, hot on the trail of a Chicago Outfit thug with stars in his eyes. Amidst the palm trees and swimming pools, Dan and Alana journey to the dark side of 1940s Hollywood, rife with tyrannical studio heads, corrupted unions, and the stark threat of mob violence. Plus, what happens when Mickey Mouse goes union busting.


    Sources

    The Disney Revolt: The Great Labor War of Animation's Golden Age by Jake S. Friedman

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

    Shadow of the Racketeer: Scandal in Organized Labor by David Witwer

    The Hollywood Connection : The True Story of Organized Crime in Hollywood by Michael Munn


    Time Magazine, Reader's Digest, Omaha World-Herald, Cleveland Plain Dealer, Chicago Daily News, Los Angeles Times, Kansas City Times, Associated Press, The Birmingham News, Tulsa World, San Francisco Examiner, Chicago Tribune, The Daily Worker, Los Angeles Evening Citizen News, Variety, The Hollywood Reporter, U.P., Los Angeles Daily News, Long Beach Independent, Los Angeles Mirror.

    ---

    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.

    Más Menos
    58 m
  • The Kray Twins: London's Master Blackmailers
    Oct 2 2025

    This week on The Outfit, a fateful exploration into the UK’s most infamous gangster twins and how the web of blackmail they weaved through the country’s political sphere has shocking resonance to current events. Join Dan and Alana as they delve into a British tale so English it could be parody.


    Sources:

    John Pearson, The Profession of Violence, The Cult of Violence, Notorious

    John Dickson, Murder Without Conviction

    Daniel Smith, The Peer and the Gangster: A Very British Cover-Up


    The Daily Mail, The Daily Mirror, Sunday Mirror, The Times (London), The Guardian, Daily Express, The Independent, The Observer, The Daily Telegraph, GQ, Politico, BBC, Channel 4.

    ---

    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

    Managing Producer is Tiffany Hammond

    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.

    Más Menos
    1 h y 7 m
  • William Handhardt: The Celebrity Cop
    Sep 25 2025

    This week, Dan and Alana discuss William Hanhardt, who rose to become chief of Detectives in the Chicago Police Department. Subject of the hit television series, "Crime Story" and technical advisor on Michael Mann's "Thief," Handhardt was a cop's cop gone Hollywood: a no-nonsense tough guy whose squad inspired the cops in crime classic, "Heat." But behind the badge was a far more sobering reality, uncomfortably intertwined with the Outfit.


    Sources:

    Family Secrets: The Case That Crippled the Chicago Mob by Jeff Coen

    Mob Cop: My Life of Crime in the Chicago Police Department by Fred Pascente with Sam Reaves

    A Gun in My Gucci: Two Outsiders Take Down the Chicago Mob by E.C. Smith

    Newspapers and magazines including The Chicago Tribune, The Chicago Sun-Times, The Chicago Reader, and The Atlantic.

    ---

    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

    Managing Producer is Tiffany Hammond

    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.

    Más Menos
    59 m