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Underbelly: Killing KurtKilling Kurt Author: Entropy Media
For decades, Kurt Calabrese lived in the shadow of his father, Frank The Breeze Calabrese Sr., one of the Chicago Outfits most feared hitmen and loan sharks. Raised in a home ruled by violence, paranoia, and control, Kurt grew up knowing that loyalty wasnt 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 Kurts 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 Kurtalong with other gripping Entropy showscompletely ad-free by subscribing to Entropy Unlimited on Apple Podcasts. Unlock exclusive access and e Language: en Genres: History, True Crime Contact email: Get it Feed URL: Get it iTunes ID: Get it Trailer: |
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S3 E08: The Final Errand
Episode 8
Wednesday, 14 May, 2025
In the final chapter of Killing Kurt, Kurt Calabrese travels to a remote house in North Carolina to confirm his father’s death. What begins as a simple errand turns into an emotional reckoning. Inside a dim room behind a red curtain, Kurt comes face to face with the body of Frank Calabrese Sr.—the man who dominated, abused, and haunted his life. For the first time, Kurt is able to speak freely to his father, unleashing years of pain, rage, and conflicted love. As Kurt seeks closure, the fallout from Operation Family Secrets continues. Federal agents raid Frank Sr.’s home and uncover hidden stashes of cash, diamonds, guns, and tapes—evidence of a criminal empire now reduced to dust. With the Outfit in decline and the family fractured beyond repair, Kurt reflects on what it truly means to survive a legacy built on violence, fear, and silence. Binge the entire season of Killing Kurt—along with other gripping Entropy Media shows—completely ad-free by subscribing to Entropy Unlimited on Apple Podcasts. Unlock exclusive access to bonus content and enjoy your favorite stories without interruptions. Click HERE to learn more! Learn more about your ad choices. Visit podcastchoices.com/adchoices
