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

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Al Capone All-American: The St. Valentine's Day Massacre

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.

1 Std. 3 Min.
5. FEB.

Al Capone All-American: Cicero & Politics

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.

59 Min.
29. JAN.

Al Capone All-American: The North Side Mob

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.

1 Std.
22. JAN.

Al Capone All American: Prohibition

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.

1 Std. 2 Min.
15. JAN.

Al Capone All-American: Torrio vs Colosimo

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.

52 Min.
8. JAN.

Al Capone All-American: Young Capone & Frankie Yale

Before he was Al Capone — the Scarface of popular myth — he was Alphonse Capone. In this inaugural episode of The Outfit’s first ever limited series, Dan and Alana take a trip back in time to dissect the man that made the man. Where a Brooklyn-born child of immigrants, under the tutelage of one very sinister Coney Island mentor, began his journey from a lowly shoeshiner to dominating the Jazz Age so thoroughly that he still remains synonymous with organized crime today. Sources: Historian Mario Gomes's excellent website, My Al Capone Museum (https://www.myalcaponemuseum.com/) The Mammoth Book of Journalism by Jon E. Lewis Al Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition by John Binder 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 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.

1 Std.
18.12.2025

Tony Accardo: The Chicago Godfather's Bloody Christmas

It's a Very Outfit Christmas this holiday season, as Dan and Alana bring you their own version of yuletide cheer: 'twas (not quite) the night before Christmas 1977, when a crew of burglars, stung over their own gift-giving, played Santa in the home of Outfit overlord Tony Accardo…and ended up on a permanent naughty list. Grab some cookies, pour some eggnog, and settle in for the bloodiest tale in Christmas history. Sources: Hillel Levin, "Boosting The Big Tuna," Playboy, 2007. The Chicago Tribune, The Chicago Sun-Times, Chicago Reader, Chicago Magazine, Time Magazine. William Roemer, Accardo: The Genuine Godfather. Jeff Coen, Family Secrets: The Case That Crippled The Chicago Mob. Fred Pascente & Fred Reaves, Mob Cop: My Life of Crime in the Chicago Police Department. --- 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.

1 Std. 10 Min.
11.12.2025

Goodfellas with Allie Kahan

This week, Dan and Alana take on an age-old mystery: why are straight men so obsessed with Goodfellas? They’re joined by Allie Kahan, content manager at Headgum, for a deep-dive into their favorite scenes, classic Scorsese-isms, and the surprisingly queer heart of the mob-movie canon. --- 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.

58 Min.

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TRAILER

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

06.08.2025

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1 Min.

Join the staff of the Headgum network as they try to navigate a series of quizzes, games and conversation enders poised by their coworker Geoffrey James. If you have questions, email in to hgpod@headgum.com.

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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