Underbelly: Killing Kurt

Underbelly: Killing Kurt

For decades, Kurt Calabrese lived in the shadow of his father, Frank “The Breeze” Calabrese Sr., one of the Chicago Outfit’s most feared hitmen and loan sharks. Raised in a home ruled by violence, paranoia, and control, Kurt grew up knowing that loyalty wasn’t a choice, it was survival. In 2007, the Family Secrets Trial exposed 18 unsolved murders and a laundry list of heinous crimes that had terrorized Chicago for decades. Based on wiretap evidence from Kurt’s brother Junior, the case led to life sentences for some of the most powerful mob figures in modern history, effectively dismantling the Chicago Outfit. But the trial was just the public reckoning. The real story began years earlier, inside the Calabrese family itself. Season 3 of the award-winning podcast Underbelly, “Killing Kurt” takes listeners back to where it all began. Beyond the headlines and the courtroom, this is the story of a crime family at war with itself. As Kurt wrestled with his own loyalty, his older brother committed the ultimate betrayal, setting off a chain of events that would not only take down their father but leave Kurt caught in the crossfire. Told through his firsthand account, Kurt reveals the untold cost of growing up in the mob, the violence at home, the psychological toll, and the impossible choices made to escape a legacy of fear. Listen to the all new season of Underbelly: Killing Kurt, premiering April 2nd. Available wherever you get your podcasts. --------------- Underbelly is a podcast series exploring the wild and true stories behind investigations into the underbelly of society. From enigmatic spies, to seedy criminals and crooked officials, to the upper echelons of government intelligence, we shine light on the underworld through never before heard revelations about crimes you never dared to imagine. Binge the entire season of Killing Kurt—along with other gripping Entropy shows—completely ad-free by subscribing to Entropy Unlimited on Apple Podcasts. Unlock exclusive access and enjoy your favorite stories without interruptions. Click the HERE to learn more!

Episodes

Underbelly: Brokers, Bagmen, & Moles - Season 1 Trailer

April 4, 2023 • 2 mins
When you picture the 1980s’ Wall Street boys’ club, you might not think of Chicago. But in 1987, its Mercantile Exchange dwarfed the New York Stock Exchange in both dollars and international influence. Member-owned and expanding rapidly, how it worked—or who was working it—was more obscured. That’s when the FBI stepped in. The Feds sought to shine light upon it through a high-stakes operation, the most expensive in its history, to ...
Mark as Played

S1 02: T-Bun and the G Men

April 26, 2023 • 39 mins
To understand this case, you need to meet the colorful cast of characters at its core: Chicago commodities traders. Meet part-time bookie, possible mob associate, and full-time trader Tony “T-Bun” Bonjourno. He’s a blue collar guy whose dad’s friend helped him get a job on the floor. Once there, T-Bun and his friends live a life beyond their wildest fantasies. T-Bun gives us our first glimpse of the FBI agents’ actions on the floor...
Mark as Played

S1 01: The Biggest Small Town in the World

April 26, 2023 • 35 mins
In the 1980s, blue collar kids started making millions at Chicago’s commodities exchanges. This century-old boys' club was one of the best-kept secrets in the world until the FBI showed up and tried to end the party. The FBI investigation put the exchanges on front pages everywhere, but when the Feds packed up, business went back to usual—like they’d never been there. Thirty years later, former-trader-turned-Hollywood exec Anjay Na...
Mark as Played

S1 03: Knock Knock. Who's There?

May 3, 2023 • 38 mins
The ‘80s were a time of tremendous growth on the floor, creating opportunities for guys like boxer Ray Pace. Ray went from working part-time on movie sets to trading for one of the largest brokerage groups at the Merc, ABS Partners. Little did he know, by 1987, he was standing next to an undercover agent. In the grand scheme of things, Ray was a small fish, so Anjay questions if his role with the controversial ABS is what put him o...
Mark as Played

S1 04: Scapegoats and Fat Cats

May 10, 2023 • 45 mins
Pulitzer prize-winning journalist Bill Crawford broke the news of the undercover investigation in January 1989, when an unnamed source in Washington, D.C. tipped off the Chicago Tribune. The Trib’s initial stories billed the case as a tremendous win for the government, but right away, Crawford questioned if the government had missed its mark—could they perhaps have been gunning for the men in charge of the exchanges? Anjay then spe...
Mark as Played

S1 05: The Informant?

May 17, 2023 • 37 mins
Within a week of breaking the story, the press learned that the FBI came to Chicago’s exchanges partly in response to a complaint from a powerful agricultural company called Archer Daniels Midland. While that remains the popular narrative, Anjay’s sources convince him that the government has managed for decades to keep something about this case secret—but what, exactly? In this episode, we learn about the government’s attempts to g...
Mark as Played

S1 06: Traders and Traitors

May 31, 2023 • 41 mins
Someone was bound to talk eventually, and it ended up being one of the white-collar kids at the Chicago Board of Trade. Anjay speaks with trader Dave Skrodzki about his decision to cooperate, what it meant for his livelihood, and why Skrodzki thinks the government found exactly what it was looking for in Chicago. While Skrodzki and a few other cooperators helped the FBI solidify a few cases, the Feds ultimately didn't produce nearl...
Mark as Played

S1 07: Big Fish

June 7, 2023 • 46 mins
The man, the myth, the target of this investigation? That’s Lewis Borsellino… at least, according to Lewis Borsellino. The son of a mafia hitman, Borsellino made a name for himself as one of the most successful traders in the S&P 500 futures pit. That got the Feds interested in him, or so the story goes. Borsellino tells Anjay he suspects there's more to it than that, and Anjay decides there is only one way to get answers: speaking...
Mark as Played

S1 08: Just Be Yourself

June 14, 2023 • 55 mins
After nearly eight months of off-the-record conversations, two FBI agents agree to speak with Anjay on the record. Randy Janett and Mike Bassett tell Anjay their side of the story. They're open about why this investigation ended when it did, but when it comes to what inspired the FBI to send agents to the floor in the first place, will they stick with the public narrative, or will they reveal some cracks in it? Notes: Head to DRINK...
Mark as Played

S1 09: It Was All Chaos

June 21, 2023 • 49 mins
Defense attorneys come out swinging, in an attempt to whip up a furor over the dozens of charges against Merc traders. But they have a tough time getting jurors to understand how the buying and selling of future contracts work—not to mention keeping them awake—and the trials descend into chaos. In the end, how many traders were found guilty? And how do the agents who worked the case view its legacy now? Anjay has the surprising ans...
Mark as Played

S1 10: How to Buy An Industry

June 28, 2023 • 43 mins
As the trials wrapped up, Congress held a series of hearings that questioned how these markets should be regulated. In echoes of those trials, Congressmen displayed varying levels of comprehension of how the Merc & CBOT worked, and it turns out that those who did understand might be a little too familiar with the heads of those exchanges. As the inquiry winds down, clear winners and losers emerge. Meanwhile, Anjay has a phone call ...
Mark as Played

S1 11: A Humble Accountant

July 12, 2023 • 45 mins
More stories of mob ties among traders come to the surface, so Anjay decides to call one more agent—the one with a background in organized crime, and who seems most willing to speak with him: Dietrich Volk. Anjay arrives in a remote part of Colorado to interview the former agent, and at long last, we learn the truth of this investigation. By the end of their conversation, Anjay thinks he might be able to prove what the agents never...
Mark as Played

S1 12: The Durkin Document

July 19, 2023 • 55 mins
Trying to find more concrete evidence that the FBI was actually on the floor to investigate the ties between organized crime and Chicago’s exchanges, Anjay searches through thousands of pages of court transcripts. What he finds isn’t quite what he was looking for—instead, he discovers a legal brief that leads him down a completely unforeseen and even more shocking path. What happened to this smoking gun, and why was nothing ever do...
Mark as Played

Join Us LIVE in Chicago, Tuesday October 3!

September 27, 2023 • 1 min
Join host Anjay Nagpal and special guests from Brokers, Bagmen, & Moles for a live panel discussion and Q&A! We'll share stories from behind-the-scenes of the production, answer your burning questions about the wild stuff that went down on the trading floor, and share some laughs (and tacos). This FREE event will be at the Texan Taco Bar in Chicago's West Loop (942 W Randolph St), next Tuesday, October 3, from 5-6:30pm. Space is li...
Mark as Played

Underbelly S1 Brokers, Bagmen, & Moles: Live Q&A in Chicago

October 26, 2023 • 69 mins
Underbelly creator & host Anjay Nagpal, showrunner Danielle Elliot, "Brokers, Bagmen, & Moles" book co-author David Greising, and traders/fan favorites Tim, Stretch, & T-Bun got together at the Texas Taco Bar in Chicago to have a live panel discussion and Q&A. If you missed it, you can still enjoy hearing about the origins of the investigation, the struggles & successes bringing it to life in audio, a few more stories from the floo...
Mark as Played

Underbelly: The Rebel Kind Trailer - Out March 13

February 29, 2024 • 3 mins
The Rebel Kind is the unreal, real-life story of Dave Rupert—a six-foot-seven Chicago trucker who infiltrated the heart of a dangerous faction of the Irish Republican Army. From Entropy Media, the second season of the Underbelly series focuses on the unlikely man with entrepreneurial dreams and a willingness to do whatever it takes to get the job done. Veteran journalists Bob Herguth and Abdon Pallasch tell the story through tape r...
Mark as Played

S2 E01: There Once Was A Trucker From Chicago

March 13, 2024 • 44 mins
Meet Dave Rupert. A guy born in a part of Upstate New York so rural it's practically Canada, with a past nearly as untamed: trucker, one-time professional wrestler, pilot, a bit of a serial entrepreneur. Meet Mickey McKevitt. An ocean away, he leads the Irish Republican Army's militant splinter cell, the Real IRA. The two men had seemingly nothing in common, but by the time they met, Dave had earned the trust of the group as though...
Mark as Played

S2 E02: A Little Bit Off Base

March 20, 2024 • 45 mins
When an FBI agent walks into Dave Rupert's truck stop, his mind starts racing. There's so many things law enforcement might want to address. A few friends he made though a dalliance is the last thing on his mind. Dave Rupert's unusual background in upstate New York led from a family doing what they had to do to survive to becoming a trucking entrepreneur. But a night out at a bar in Florida will eventually change Dave's life.  Addi...
Mark as Played

S2 E03: The FBI Walks Into a Bar

March 27, 2024 • 46 mins
Dave Rupert experiences a little indigestion as he mulls over an offer from the FBI. He'll learn the agent who approached him has a background in investigating international terrorism back in Chicago. In fact, Ed Buckley is well known to Irish Republican supporters in the city. When Dave sees an opportunity to make some money, he goes for it.  Learn more about your ad choices. Visit podcastchoices.com/adchoices
Mark as Played

S2 E04: It's a Funny Place, Tullaghan

April 3, 2024 • 46 mins
Dave's plot to run a bar for profit while spying on vacationing republicans along the banks of the Drowes River is a rocky as the road to Dublin. The former owner of his pub wasn't paying the bills and that makes Dave's life even more difficult. But a diligent barkeep certainly doesn't look like a spy and his plan kind of begins to work. Knowing the history of the British occupation in Ireland is just the tip of the iceberg for Dav...
Mark as Played

Popular Podcasts

    On Purpose with Jay Shetty

    On Purpose with Jay Shetty

    I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

    Stuff You Should Know

    Stuff You Should Know

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

    Dateline NBC

    Dateline NBC

    Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

    The Clay Travis and Buck Sexton Show

    The Clay Travis and Buck Sexton Show

    The Clay Travis and Buck Sexton Show. Clay Travis and Buck Sexton tackle the biggest stories in news, politics and current events with intelligence and humor. From the border crisis, to the madness of cancel culture and far-left missteps, Clay and Buck guide listeners through the latest headlines and hot topics with fun and entertaining conversations and opinions.

    The Joe Rogan Experience

    The Joe Rogan Experience

    The official podcast of comedian Joe Rogan.

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

Explore

iHeart

Live Radio

Podcasts

Artist Radio

Exclusives

News

Features

Events

Contests

Photos

Information

About

Advertise

Blog

Brand Guidelines

Contest Guidelines

Subscription Offers

Jobs

Get the App

Automotive

Home

Mobile

Wearables

© 2025 iHeartMedia, Inc.