Headgum // The Outfit

The Outfit

with Alana Hope Levinson and Dan O'Sullivan

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

The Outfit

Al Capone All-American: Downfall and the Feds 3/5/2026

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: @alanalevinson

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The Outfit

Al Capone All-American: Jake Lingle and the Media 2/26/2026

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.

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The Outfit

Casino with Demi Adejuyigbe 2/19/2026

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.

The Outfit

Al Capone All-American: The St. Valentine's Day Massacre 2/12/2026

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.

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Al Capone All-American: Cicero & Politics 2/5/2026

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.

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The Outfit

Al Capone All-American: The North Side Mob 1/29/2026

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.

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The Outfit

Al Capone All American: Prohibition 1/22/2026

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.

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The Outfit

Al Capone All-American: Torrio vs Colosimo 1/15/2026

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?

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The Outfit

Al Capone All-American: Young Capone & Frankie Yale 1/8/2026

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.

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The Outfit

Tony Accardo: The Chicago Godfather's Bloody Christmas 12/18/2025

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.

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The Outfit

Goodfellas with Allie Kahan 12/11/2025

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

Robert Kubecka: Garbage & The Mob 12/4/2025

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.

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Growing Up Gotti with Misha Brown 11/20/2025

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

Martin Cahill: "The General" & Ireland's Underworld 11/13/2025

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.

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The Outfit

Charles Becker: The NYPD's Killer Cop 11/6/2025

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.

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