The Outfit

The Outfit

Host: Headgum

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

Episodes

Willie Bioff: Labor Racketeering in Hollywood's Golden Age
01October 09, 2025 3:00amExplicit

Willie Bioff: Labor Racketeering in Hollywood's Golden Age

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 stud…

The Kray Twins: London's Master Blackmailers
02October 02, 2025 3:00am

The Kray Twins: London's Master Blackmailers

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 d…

William Handhardt: The Celebrity Cop
03September 25, 2025 3:00amExplicit

William Handhardt: The Celebrity Cop

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…

The Mafia & Gay Bars: The Raid on Louie's Fun Lounge
04September 18, 2025 3:00amExplicit

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

 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…

World Trade Center: The Towers the Mob Built
05September 11, 2025 3:00amExplicit

World Trade Center: The Towers the Mob Built

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 frau…

Paul Tatum: The American Cowboy in Russia
06September 04, 2025 3:00amExplicit

Paul Tatum: The American Cowboy in Russia

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 int…

George Remus: The Real Great Gatsby
07August 28, 2025 3:00amExplicit

George Remus: The Real Great Gatsby

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…

Ken Eto: The Japanese-American Mafiosi
08August 21, 2025 3:00amExplicit

Ken Eto: The Japanese-American Mafiosi

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 fa…

Welcome to The Outfit!
09August 14, 2025 3:00amExplicit

Welcome to The Outfit!

On this, the day of the very first episode of The Outfit, Dan and Alana revisit one of the most famous mobsters to ever live: Al Capone. Plus, they look at how the mafia has shaped American life in surprising ways — and how it helps explain…

Introducing The Outfit with Alana Hope Levinson and Dan O'Sullivan
10August 06, 2025 12:00pm

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

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 a…