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Underbelly: Killing Kurt
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Underbelly: Killing Kurt

Author: Entropy Media

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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.


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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!

39 Episodes
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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 limited, and we'll be prioritizing RSVPs that come with a question. Share yours by DMing us @entropymediaco or emailing us [email protected]. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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 expose corruption at Chicago’s Merc and Board of Trade. What ensued was an elaborate undercover investigation resulting in dozens of indictments for traders who were accused of conspiring to defraud farmers, banks, pension funds, and other customers from around the world. The government either had itself a huge success that reformed our financial markets, or it was total flop—it all depends who you ask. Led by host Anjay Nagpal, after more than thirty years, Brokers, Bagmen, & Moles gets to the truth. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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 Nagpal thinks there's something strange about this case. He taps his Chicago connections and after a few calls, he's already poking holes in the government's long-accepted narrative of the investigation. Notes: You can find episode transcripts and more on our website at https://www.entropymedia.art/brokers-bagmen-moles. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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 and tells an incredible story that might just be the answer to why this investigation ended prematurely. Notes: You can find episode transcripts and more on our website at https://www.entropymedia.art/brokers-bagmen-moles. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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 on the Feds' radar. The agents say he committed felonies; Ray says he was just doing business the way he was taught. All this leads Anjay to a new idea: Was Ray just a scapegoat, a way for the FBI to cover up its own failure? Notes: You can find episode transcripts and more on our website at https://www.entropymedia.art/brokers-bagmen-moles. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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