
Advertise on podcast: The Outfit
Rating
4.4from
This podcast has
28 episodes
Language
EnglishPublisher
HeadgumExplicit
Yes
Date created
2025/08/06
Latest episode
2026/03/05
Average duration
60 min.
Release period
9 days
Description
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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Check latest episodes from The Outfit podcast
Al Capone All-American: Downfall and the Feds
2026/03/05
SUBSCRIBE TO THE NEW HOME OF THE OUTFIT ON PATREON! https://www.patreon.com/TheOutfitPod
Parting 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: @alanalevinson
Sources
Historian 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 Interesting
Get Capone: The Secret Plot That Captured America's Most Wanted Gangster by Jonathan Eig
Eliot Ness: The Rise and Fall of an American Hero by Douglas Perry
Scarface and the Untouchable: Al Capone, Eliot Ness and the Battle for Chicago by Max Allan Collins & A. Brad Schwartz
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 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 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.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Al Capone All-American: Jake Lingle and the Media
2026/02/26
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.
Sources
Historian 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 Schwartz
All Things Considered by Howard Vincent O'Brien
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 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 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.
Casino with Demi Adejuyigbe
2026/02/19
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 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.
Al Capone All-American: The St. Valentine's Day Massacre
2026/02/12
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.
Al Capone All-American: Cicero & Politics
2026/02/05
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.
Al Capone All-American: The North Side Mob
2026/01/29
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.
Al Capone All American: Prohibition
2026/01/22
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.
Al Capone All-American: Torrio vs Colosimo
2026/01/15
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.
Al Capone All-American: Young Capone & Frankie Yale
2026/01/08
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.
Tony Accardo: The Chicago Godfather's Bloody Christmas
2025/12/18
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.
Goodfellas with Allie Kahan
2025/12/11
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.
Robert Kubecka: Garbage & The Mob
2025/12/04
This week, Dan travels back to the land of his birth--Long Island, New York--for a fragrant stroll past one of the Mafia's biggest moneymakers: garbage. As he and Alana find out, the garbage industry was a critical source of money to New York's Five Families, the cost passed on to everyone else. Until one honest garbage hauler--Robert Kubecka--decided to do something about this stranglehold, in a saga which would dominate Long Island news for years.
Sources
"Garbage, Dentists, and Mobsters – Resource Capital Group’s LCN Connections," Mafia Book Reviews, 2022.
Alan A. Block, Space, Time, and Organized Crime.
Alan A. Block & Frank R. Scarpitti, Poison for Profit: The Mafia and Toxic Waste in America.
New York Newsday, New York Daily News, New York Post, The New York 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.
Growing Up Gotti with Misha Brown
2025/11/20
On this week's episode of The Outfit, Dan and Alana are joined by Misha Brown, podcaster and author of upcoming new book, Be Your Own Bestie, to dish on A&E's Growing Up Gotti: The 2004 reality hit following Victoria Gotti and her three teenage sons. From dating to daddy issues, our hosts take a look at all the baggage that comes with being a nepo-mobster.
Check out: Be Your Own Bestie: A No Nonsense Guide to Changing the Way you Treat Yourself by Misha Brown
---
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.
Martin Cahill: "The General" & Ireland's Underworld
2025/11/13
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).
---
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.
Charles Becker: The NYPD's Killer Cop
2025/11/06
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.
---
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.
Podcast reviews
Read The Outfit podcast reviews
Please I’m Begging You 2026/06/21
GOATed
Dan O the GOAT
My Dooood 2026/05/04
Worst podcaster on the planet
Glad his show seems to have ended. Please stop appearing on Guys
UCLA-Greek 2026/03/13
Love the Show
Great show. I have always been attracted to the mob general but in particular Chicago because of their composition make up of their organization (espe...
M.E. 2012 2026/03/02
Creative and Entertaining
Each episode holds your interest. Well written and executed. Alana and Dan are so fun to listen to.
Shopkin 101😀😀😁 2026/02/07
Love this show!
Love the history! Keep doing what you’re doing. Don’t listen to the haters.
Nevpaurion9 2026/02/06
Great pod
Love the banter and the tie ins to modern politics. History doesn’t always repeat but it sure does rhyme. Keep calling out the parallels and ignore th...
spork oracle 2026/02/06
Al Capone Stories
I’m really enjoying listening to the Al Capone stories and the hosts do an excellent job of being both entertaining and informative. I would like to h...
lantern314 2026/02/05
Great historical context
Very fun podcast. The hosts are engaging and it feels well researched. Keep up the good work. The reviewers who are complaining about the politics are...
AlexandraDartt 2026/02/02
Too Rambling
I want to love this so bad - I’m up to date with the Al Capone episodes and am so confused after each episode. I love that the hosts are having fun bu...
nedmitchell 2026/01/10
Love this show
Incredible to find an actually fresh take on US politics. Entertaining, engaging, informative. Great work!
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