The Outfit – Details, episodes & analysis

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The Outfit

Headgum

History

True Crime

Society & Culture

Frequency: 1 episode/7d. Total Eps: 20

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

Recent rankings

Latest chart positions across Apple Podcasts and Spotify rankings.

Apple Podcasts

🇺🇸 USA - history
10/01/2026
#91
🇺🇸 USA - history
09/01/2026
#89
🇺🇸 USA - history
08/01/2026
#87
🇺🇸 USA - history
07/01/2026
#64

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https://gumball.fm/shows/the-outfit
17 shares
https://headgum.com/
3 shares
https://highergroundmedia.com/
2 shares

https://podcasts.apple.com/us/podcast/the-outfit/id1831566512
17 shares

https://www.tiktok.com/@headgum
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RSS feed quality

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Score global : 63%

Publication history

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Latest published episodes

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Introducing The Outfit with Alana Hope Levinson and Dan O'Sullivan

Wednesday, August 6, 2025 • Duration 00:41

Welcome to The Outfit premiering August 14th. 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. Produced by Higher Ground and Headgum.

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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Ken Eto: The Japanese-American Mafiosi

Thursday, August 21, 2025 • Duration 01:02:00

Dan and Alana revisit the story of Ken Eto, nicknamed “Tokyo Joe,” whose experience of racist persecution and American internment camps set him up for a life lived in the margins — and high up inside the Chicago Outfit. That is, before a fabulous FBI agent with a gun in her Gucci derails his underworld climb.

Sources:

Read Dan’s *award winning* Chicago Magazine story on Ken Eto here!

Watch the episode on YouTube here!

Like the show? Rate The Outfit on Spotify and Apple Podcasts and leave a review.

This is a Headgum podcast. 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.

George Remus: The Real Great Gatsby

Thursday, August 28, 2025 • Duration 01:01:27

On today’s episode of The Outfit, Dan and Alana head to Prohibition-era Cincinnati, where a former lawyer-turned-bootlegger becomes a mark for an ambitious conwoman. Plus, Dan and Alana reminisce on sophomore year English class.

Sources:

King of the Bootleggers: A Biography of George Remus by William A. Cook

The Ghosts of Eden Park: The Bootleg King, the Women Who Pursued Him, and the Murder That Shocked Jazz-Age America by Karen Abbott

The Bourbon King: The Life and Crimes of George Remus, Prohibition's Evil Genius by Bob Batchelor

Prohibition by Jeff Hill

The newspaper archives of the Chicago Tribune, The Cincinnati Enquirer, the Chicago Daily News, the Cincinnati Post, the Kentucky Post, the Pittsburgh Press, The Dayton Herald, Detroit Free Press, the New York Daily News, The Cleveland Press, and the St. Louis Post-Dispatch.

Like the show? Rate The Outfit on Spotify and Apple Podcasts and leave a review.

Paul Tatum: The American Cowboy in Russia

Thursday, September 4, 2025 • Duration 56:58

When American businessman Paul Tatum set up shop in post-Soviet Moscow, he thought he was building the first outpost of what would become a luxury hotel empire, ushering Russia into the "End of History" '90s. Instead, he walked straight into Moscow's underworld. This week, Dan and Alana find out what happens when Americans act ugly abroad, and learn how corruption helped create the Russia of today.

Sources

Stranded in Moscow by Rick Furmanek

Violent Entrepreneurs: The Use of Force in the Making of Russian Capitalism by Vadim Volkov

Mafia Life: Love, Death and Money at the Heart of Organized Crime by Federico Varese

Print sources include The Daily Oklahoman, BBC, The Los Angeles Times, The Moscow Times, OC Weekly, Tulsa World, The Associated Press, The Minneapolis Star Tribune, FORTUNE, and Time Magazine.

The Outfit is a production of Higher Ground and Headgum.

Hosted 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

The Mafia & Gay Bars: The Raid on Louie's Fun Lounge

Thursday, September 18, 2025 • Duration 56:23

This week, what does it mean to make a deal with the devil? Dan and Alana examine Richard Ogilvie and his tumultuous path to governor of Illinois, and whether the moral compromises he made to get there were worth the legacy (or lack of one) he leaves behind. Plus, the shocking history of mafia infiltration of queer nightlife, and how corrupt policing and homophobia continue to resound today.

Sources:

Newspapers including The Chicago Tribune, The Chicago Sun-Times, The Chicago Reader, The Windy City Times, Arlington Heights Daily Herald, The Daily Calumet, Columbia Journalism Review, Chicago American, Chicago Daily News.

PBS SoCal

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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

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 .

World Trade Center: The Towers the Mob Built

Thursday, September 11, 2025 • Duration 01:05:13

On the 24th anniversary of the 9/11 attacks, Dan and Alana dig into a shockingly under-examined story: how the mafia profited from the World Trade Center. From its inception to collapse in Lower Manhattan, the center’s construction was fraught with incompetence and political corruption.

Sources

Grand Illusion: The Untold Story of Rudy Giuliani and 9/11 by Wayne Barrett and Dan Collins

The Unthinkable Happened: The Fall of the World Trade Center Towers by Charlie Thornton

Manufacturing Discontent: The Trap of Individualism in Corporate Society by Michael Perelman

Never Enough: Donald Trump and the Pursuit of Success by Michael D'Antonio

The Gotti Tapes: The Sensational FBI Tapes That Convicted America's Most Powerful Mobster by Ralph Blumenthal

Mob Star: The Story of John Gotti by Gene Mustain and Jerry Capeci

Crime Scene: World Trade Center by J. R. de Szigethy

World Trade Center Building Performance Study, FEMA, May 2002

William Handhardt: The Celebrity Cop

Thursday, September 25, 2025 • Duration 58:46

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.

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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

Managing Producer is Tiffany Hammond

Show theme is Bittersweet Defeat by OTE

Like the show? Rate The Outfit on and and leave a review.

The Kray Twins: London's Master Blackmailers

Thursday, October 2, 2025 • Duration 01:06:37

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.

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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

Willie Bioff: Labor Racketeering in Hollywood's Golden Age

Thursday, October 9, 2025 • Duration 58:04

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.

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The Outfit is a production of Higher Ground and Headgum.

The Outfit – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Shared links between episodes and podcasts

RSS feed quality and score

Publication history

Latest published episodes

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

Related Shows Based on Content Similarities

The Outfit – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Shared links between episodes and podcasts

Other28

Apple Podcast1

Tik Tok1

RSS feed quality and score

Publication history

Latest published episodes

Similar podcasts and content

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

Related Shows Based on Content Similarities

Other28

Apple Podcast1

Tik Tok1