The Outfit
The Outfit
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
Al Capone All-American: Downfall and the Feds
SUBSCRIBE TO THE NEW HOME OF THE OUTFIT ON PATREON! https://www.patreon.com/TheOutfitPodParting 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: @alanalevinsonSourcesHistorian 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 InterestingGet Capone: The Secret Plot That Captured America's Most Wanted Gangster by Jonathan EigEliot Ness: The Rise and Fall of an American Hero by Douglas PerryScarface and the Untouchable: Al Capone, Eliot Ness and the Battle for Chicago by Max Allan Collins & A. Brad SchwartzCapone: The Man and the Era by Laurence BergreenMr. Capone: The Real - and Complete - Story of Al Capone, by Robert J. SchoenbergCapone: The Life and World of Al Capone by John KoblerAl Capone: His Life, Legacy, and Legend by Deirdre BairThe Wicked City: Chicago From Kenna to Capone by Curt Johnson with R. Craig SautterAl Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition by John BinderGangland Chicago: Criminality and Lawlessness in the Windy City by Richard C. LindbergProhibition Gangsters: The Rise and Fall of a Bad Generation by Marc MappenThe Outfit: The Role of Chicago's Underworld in the Shaping of Modern America by Gus RussoNewspapers 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 LevinsonExecutive Produced by Dan O’Sullivan and Alana Hope LevinsonProduced by Julia MurrayProduction Assistance by CJ Archerd and Franchesca DiazSound Design and Engineering by Ryan Kozlowski and Andrew EapenShow theme is Bittersweet Defeat by OTELike 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.
Mar 5
1 hr 2 min
Al Capone All-American: Jake Lingle and the Media
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.SourcesHistorian 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 SchwartzAll Things Considered by Howard Vincent O'BrienCapone: The Man and the Era by Laurence BergreenMr. Capone: The Real - and Complete - Story of Al Capone, by Robert J. SchoenbergCapone: The Life and World of Al Capone by John KoblerAl Capone: His Life, Legacy, and Legend by Deirdre BairThe Wicked City: Chicago From Kenna to Capone by Curt Johnson with R. Craig SautterAl Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition by John BinderGangland Chicago: Criminality and Lawlessness in the Windy City by Richard C. LindbergProhibition Gangsters: The Rise and Fall of a Bad Generation by Marc MappenThe Outfit: The Role of Chicago's Underworld in the Shaping of Modern America by Gus RussoNewspapers 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 LevinsonExecutive Produced by Dan O’Sullivan and Alana Hope LevinsonProduced by Julia MurrayProduction Assistance by Franchesca Diaz and CJ ArcherdSound Design and Engineering by Ryan Kozlowski and Andrew EapenShow theme is Bittersweet Defeat by OTELike 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.
Feb 26
56 min
Casino with Demi Adejuyigbe
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 LevinsonExecutive Produced by Dan O’Sullivan and Alana Hope LevinsonProduced by Julia MurrayProduction Assistance by CJ Archerd and Franchesca DiazSound Design and Engineering by Ryan Kozlowski and Andrew EapenShow theme is Bittersweet Defeat by OTELike 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.
Feb 19
1 hr 5 min
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.SourcesA 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 BergreenMr. Capone: The Real - and Complete - Story of Al Capone, by Robert J. SchoenbergCapone: The Life and World of Al Capone by John KoblerAl Capone: His Life, Legacy, and Legend by Deirdre BairThe Wicked City: Chicago From Kenna to Capone by Curt Johnson with R. Craig SautterAl Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition by John BinderGangland Chicago: Criminality and Lawlessness in the Windy City by Richard C. LindbergProhibition Gangsters: The Rise and Fall of a Bad Generation by Marc MappenThe Outfit: The Role of Chicago's Underworld in the Shaping of Modern America by Gus RussoNewspapers 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 LevinsonExecutive Produced by Dan O’Sullivan and Alana Hope LevinsonProduced by Julia MurrayProduction Assistance by Franchesca Diaz and CJ ArcherdSound Design and Engineering by Ryan Kozlowski and Andrew EapenShow 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.
Feb 12
1 hr 3 min
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.SourcesHistorian Mario Gomes's excellent website, My Al Capone Museum (https://www.myalcaponemuseum.com/)Capone: The Man and the Era by Laurence BergreenMr. Capone: The Real - and Complete - Story of Al Capone, by Robert J. SchoenbergCapone: The Life and World of Al Capone by John KoblerAl Capone: His Life, Legacy, and Legend by Deirdre BairThe Wicked City: Chicago From Kenna to Capone by Curt Johnson with R. Craig SautterAl Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition by John BinderGangland Chicago: Criminality and Lawlessness in the Windy City by Richard C. LindbergProhibition Gangsters: The Rise and Fall of a Bad Generation by Marc MappenThe Outfit: The Role of Chicago's Underworld in the Shaping of Modern America by Gus RussoThe 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 LevinsonExecutive Produced by Dan O’Sullivan and Alana Hope LevinsonProduced by Julia MurrayProduction Assistance by Franchesca Diaz and CJ ArcherdSound Design and Engineering by Ryan Kozlowski and Andrew EapenShow theme is Bittersweet Defeat by OTELike 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.
Feb 5
59 min
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.SourcesThe Man Who Got Away: The Bugs Moran Story by Rose KeefeThe Wicked City: Chicago From Kenna to Capone by Curt Johnson with R. Craig SautterAl Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition by John BinderGangland Chicago: Criminality and Lawlessness in the Windy City by Richard C. LindbergProhibition Gangsters: The Rise and Fall of a Bad Generation by Marc MappenAl Capone: His Life, Legacy, and Legend by Deirdre BairThe Outfit: The Role of Chicago's Underworld in the Shaping of Modern America by Gus RussoMr. Capone: The Real - and Complete - Story of Al Capone, by Robert J. SchoenbergCapone: The Life and World of Al Capone by John KoblerCapone: The Man and the Era by Laurence BergreenNewspapers 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 LevinsonExecutive Produced by Dan O’Sullivan and Alana Hope LevinsonProduced by Julia MurrayProduction Assistance by Franchesca Diaz and CJ ArcherdSound Design and Engineering by Ryan Kozlowski and Andrew EapenShow theme is Bittersweet Defeat by OTELike 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.
Jan 29
1 hr
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.SourcesHistorian 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 McGirrBootleg: Murder, Moonshine, and the Lawless Years of Prohibition by Karen BlumenthalProhibition: Thirteen Years That Changed America by Edward BehrSmashing the Liquor Machine: A Global History of Prohibition by Mark Lawrence SchradOne Hundred Percent American: The Rebirth and Decline of the Ku Klux Klan in the 1920s by Thomas R. PegramProhibition: A Very Short Introduction by W.J. RorabaughAlcoholics AnonymousAl Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition by John BinderThe Outfit: The Role of Chicago's Underworld in the Shaping of Modern America by Gus RussoGangland Chicago: Criminality and Lawlessness in the Windy City by Richard C. LindbergProhibition Gangsters: The Rise and Fall of a Bad Generation by Marc MappenThe Wicked City: Chicago From Kenna to Capone by Curt Johnson with R. Craig SautterMr. Capone: The Real - and Complete - Story of Al Capone, by Robert J. SchoenbergYoung Al Capone: The Untold Story of Scarface in New York, 1899-1925 by William and John BalsamoCapone: The Life and World of Al Capone by John KoblerCapone: The Man and the Era by Laurence BergreenNewspapers 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 LevinsonExecutive Produced by Dan O’Sullivan and Alana Hope LevinsonProduced by Julia MurrayProduction Assistance by CJ Archerd and Franchesca DiazSound Design and Engineering by Ryan Kozlowski and Andrew EapenShow theme is Bittersweet Defeat by OTELike 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.
Jan 22
1 hr 1 min
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?SourcesHistorian Mario Gomes's excellent website, My Al Capone Museum (https://www.myalcaponemuseum.com/)Al Capone: His Life, Legacy, and Legend by Deirdre BairAl Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition by John BinderThe Outfit: The Role of Chicago's Underworld in the Shaping of Modern America by Gus RussoGangland Chicago: Criminality and Lawlessness in the Windy City by Richard C. LindbergProhibition Gangsters: The Rise and Fall of a Bad Generation by Marc MappenThe Wicked City: Chicago From Kenna to Capone by Curt Johnson with R. Craig SautterMr. Capone: The Real - and Complete - Story of Al Capone, by Robert J. SchoenbergYoung Al Capone: The Untold Story of Scarface in New York, 1899-1925 by William and John BalsamoCapone: The Life and World of Al Capone by John KoblerCapone: The Man and the Era by Laurence BergreenNewspapers 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 LevinsonExecutive Produced by Dan O’Sullivan and Alana Hope LevinsonProduced by Julia MurrayProduction Assistance by Franchesca Diaz and CJ ArcherdSound Design and Engineering by Ryan Kozlowski and Andrew EapenShow theme is Bittersweet Defeat by OTELike 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.
Jan 15
52 min
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. LewisAl Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition by John BinderMr. Capone: The Real - and Complete - Story of Al Capone, by Robert J. SchoenbergYoung Al Capone: The Untold Story of Scarface in New York, 1899-1925 by William and John BalsamoCapone: The Life and World of Al Capone by John KoblerCapone: The Man and the Era by Laurence BergreenNewspapers 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 LevinsonExecutive Produced by Dan O’Sullivan and Alana Hope LevinsonProduced by Julia MurrayProduction Assistance by CJ Archerd and Franchesca DiazSound Design and Engineering by Ryan Kozlowski and Andrew EapenShow theme is Bittersweet Defeat by OTELike 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.
Jan 8
59 min
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 LevinsonExecutive Produced by Dan O’Sullivan and Alana Hope LevinsonProduced by Julia MurrayProduction Assistance by Franchesca Diaz and CJ ArcherdSound Design and Engineering by Ryan Kozlowski and Andrew EapenShow 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.
Dec 18, 2025
1 hr 10 min
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