Entropy Media

Underbelly: Killing Kurt

History EN ↓ 39 episodes

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 th...

Author

Entropy Media

Category

History

Podcast website

www.entropymedia.art

Latest episode

May 14, 2025

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Episodes

Join Us LIVE in Chicago, Tuesday October 3! 27.09.2023

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, Oc...

S1 12: The Durkin Document 19.07.2023

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 smoki...

S1 11: A Humble Accountant 12.07.2023

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...

S1 10: How to Buy An Industry 28.06.2023

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....

S1 09: It Was All Chaos 21.06.2023

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 legac...

S1 08: Just Be Yourself 14.06.2023

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...

S1 07: Big Fish 07.06.2023

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 on...

S1 06: Traders and Traitors 31.05.2023

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 F...

S1 05: The Informant? 17.05.2023

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 a...

S1 04: Scapegoats and Fat Cats 10.05.2023

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 char...

S1 03: Knock Knock. Who's There? 03.05.2023

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...

S1 01: The Biggest Small Town in the World 26.04.2023

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-tr...

S1 02: T-Bun and the G Men 26.04.2023

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 t...

Underbelly: Brokers, Bagmen, & Moles - Season 1 Trailer 04.04.2023

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...

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