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!
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By the early 1990s, Frank Calabrese Sr. had spent decades building a criminal empire fueled by fear, paranoia, and control. He taught his sons the art of survival in the mob—never use house phones, memorize payphone numbers, speak in code, and trust no one. But when Frank let his guard down for an indebted auto shop owner named Matt Russo, the cracks in his armor started to show.
What Frank saw as an opportunity to exploit a failing business, the FBI saw as the perfect way in. Russo, drowning in debt and desperate, became a federal informant and began wearing a wire in Frank’s inner circle. But gathering evidence on a man as cautious—and dangerous—as Frank Calabrese wouldn’t be easy. We go inside the FBI’s high-stakes operation to take Frank down, the meticulous way Frank shielded himself from betrayal, and the moment it all started to unravel.
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!
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S3 E02: The Man Is Nuts
Season 3 · Episode 2
Wednesday, April 2, 2025 • Duration 42:21
The complicated relationship between Kurt Calabrese and his Uncle Nick reveals how Nick became a surrogate father figure in Kurt's turbulent childhood. While Kurt's father Frank Sr. ruled through fear, Uncle Nick showed kindness—despite his increasingly dark role as an outfit hitman who would eventually participate in multiple murders for the Chicago mob. Uncle Nick was reluctantly pulled into the criminal underworld by his brother Frank Sr., who in turn answered to feared outfit captain Angelo "The Hook" LaPietra.
Kurt's life changes dramatically when he falls in love with Angela, the granddaughter of his father's boss Angelo LaPietra. Despite family pressure to stay apart, Kurt and Angela secretly marry at City Hall—a decision that sends Frank Sr. into a violent rage. What should have been a joyful wedding day turns into a terrifying chase through the streets as Kurt flees his father's wrath, culminating in a chilling warning from Uncle Nick that this forbidden marriage could get them all killed. Their story provides a haunting glimpse into how the Chicago outfit's brutal code affected even the most personal aspects of its members' lives.
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!
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S3 E01: I'll Kick You So Hard You'll Walk Funny
Season 3 · Episode 1
Wednesday, April 2, 2025 • Duration 38:44
Kurt Calabrese, son of notorious Chicago Outfit hitman Frank "The Breeze" Calabrese Sr., breaks his silence about growing up under the shadow of one of Chicago's most feared mob enforcers. His story begins with a dramatic courtroom confrontation during the historic "Family Secrets" trial, where Kurt's victim impact statement provoked his father's menacing outburst, revealing the monster that had terrorized him throughout his childhood.
Growing up in Elmwood Park, a Chicago suburb known as an enclave for Outfit members, Kurt lived a double life—neighbors saw his father as a friendly figure who handed out homemade wine, while behind closed doors, Kurt endured relentless abuse, living in constant fear of his father's return. Frank Sr. broke the traditional Outfit code by bringing his sons into "the life," forcing Kurt to collect "street tax" and teaching him disturbing techniques for violence. This first chapter of Kurt's story reveals the beginning of his journey from terrified son to someone who would ultimately help bring down one of Chicago's most notorious crime families.
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!
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"The Rebel Kind" BONUS: An interview with David Rupert (Happy St. Patrick's Day!)
Season 2
Monday, March 17, 2025 • Duration 01:17:06
In advance of the Season 3 premiere of Underbelly on April 2nd, Entropy Media brings you a special BONUS episode of The Rebel Kind in honor of St. Patrick’s Day—a story deeply tied to Ireland’s turbulent past and one man’s extraordinary role in shaping its future.
For the first time ever, David Rupert—the trucker-turned-international-informant who helped take down Real IRA leader Mickey McKevitt—breaks his silence in a rare and candid interview.
After spending years in witness protection, David reached out upon hearing Underbelly: The Rebel Kind and agreed to sit down with Abdon Pallasch and Bob Herguth, the journalists who first documented his extraordinary story. In this special bonus episode, David reflects on his double life, the high-stakes world of counterterrorism, and the personal cost of his undercover work. He also reveals what it’s like to live off the grid—and shares some jaw-dropping stories you won’t hear anywhere else.
Listen now, and for more exclusive content from Underbelly and other Entropy Media podcasts, subscribe to Entropy Unlimited on Apple Podcasts. And don’t miss the Season 3 premiere of Underbelly: Killing Kurt, on April 2nd.
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"Underbelly: Killing Kurt" Official Trailer - Premieres April 2nd!
Season 3
Wednesday, March 12, 2025 • Duration 01:58
For years, Kurt Calabrese lived under the violent rule of his father, feared Chicago hitman Frank “The Breeze” Calabrese Sr. But when his brother turned informant, their family—and the Chicago Outfit—began to fall apart. The betrayal led to a historic trial, exposing decades of unsolved murders and taking down some of the most powerful mob figures in modern history. But behind the headlines was an even darker story—one of family loyalty, fear, and survival.
Now, for the first time, Kurt reveals what it was really like growing up in the mob, the impossible choices he faced, and what it took to escape. The award winning franchise "Underbelly", returns for its long-awaited 3rd season.
The all new season of Underbelly: Killing Kurt premieres April 2nd with a two-episode debut. Subscribe or follow now so you don't miss it! Available wherever you get your podcasts.
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Introducing "Game Plan: The Wendell Brown Story" - Out Now!
Season 2
Wednesday, August 14, 2024 • Duration 01:50
A special look at the trailer for "Game Plan: The Wendell Brown Story," the newest podcast from Entropy Media. Episodes 1 & 2 available now! (Links Below)
Synopsis: After his pro football career ended, college star Wendell Brown moved to China to teach his beloved sport to youth abroad. But when the Detroit legend is assaulted at a 2016 party in the Yuzhong District, he’s the one charged with a crime. With little hope of being released by a court boasting a 99% conviction rate, Wendell must survive the Chinese prison system––one of thirty men in a cramped, single-toilet cell, and the sole Black man, American, and foreigner behind bars. He only manages to endure thanks to the fortitude football taught him—and the daring rescue mission by a group of strangers from around the world who organize through WeChat and take great risks to bring him home. The all new series "Game Plan: The Wendell Brown Story" is available now, wherever you listen to podcasts!
Listen Now...
Apple:
https://podcasts.apple.com/us/podcast/game-plan-the-wendell-brown-story/id1753345801
Spotify:
https://open.spotify.com/show/0R0o0kkYCmYsJ2LTrU6XUf?si=d7188bb91b88475b
Amazon Music:
https://music.amazon.com/podcasts/f59467cd-630b-4c0a-b4ce-c41c649c467c/game-plan-the-wendell-brown-story
iHeart Radio:
https://www.iheart.com/podcast/269-game-plan-the-wendell-brow-189067311/
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S2 E12: The Other Side of Town
Season 2 · Episode 12
Wednesday, June 5, 2024 • Duration 41:49
Dave Rupert retires to a life in hiding, reflecting on a journey that took him across the Atlantic and back. We visit an icon of Belfast that shows just how much the north has changed. We reflect on what Dave contributed to the peace in Ireland and whether a reunited Ireland could be possible in our lifetime.
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S2 E11: McKevitt v. Pallasch
Season 2 · Episode 11
Wednesday, May 29, 2024 • Duration 52:31
Dave Rupert's contract was just for intelligence gathering, but now he's asked to testify in court. Will he out himself as an agent and informer, furthering putting himself and his family in danger? When Mickey McKevitt faces charges under a new law in the Irish Special Criminal Court, his lawyers are going to have to dig deep to discredit a potential witness. That's when they get wind of a book deal back in Chicago.
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S2 E10: Spying on Mickey
Season 2 · Episode 10
Wednesday, May 22, 2024 • Duration 37:02
After years of hard work and learning the ins and outs of Irish republicanism, Dave Rupert is in with the Real IRA. He's rubbing shoulders with one of the most dangerous men in Ireland. Dave is fast friends with the man who Irish and British governments say is the terrorist who must be stopped to prevent another tragedy like Omagh. Dave knows how to work his angles, but he worries about whether the security services can keep up.
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S2 E09: The Two Mickeys
Season 2 · Episode 9
Wednesday, May 8, 2024 • Duration 42:26
The last militant Republicans still willing to fight after the Omagh bombing are looking for support. What better support could you ask for than a wealthy American offering cash and weapons from the United States? Joe O'Neil introduces Dave Rupert to a storied Republican named Mickey Donnelly and with that connection, Dave is whisked off to a meeting with the Real IRA's top man: Mickey McKevitt.
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