Dave Rupert has spent years earning the trust of his IRA friends in Ireland and they've finally given him a military task. Dave heads back to Chicago with a name: Frank O'Neill. He's about to discover why an FBI agent like Ed Buckley was tasked with rooting out any connections between Chicago and militant Republicans. Dave's next moves will be in a city that goes as far as dyeing a whole river green on St. Patrick's Day.  Learn more about your ad choices. Visit <a href="https://podcastchoices.com/adchoices">podcastchoices.com/adchoices</a>

Dave Rupert has spent years earning the trust of his IRA friends in Ireland and they've finally given him a military task. Dave heads back to Chicago with a name: Frank O'Neill. He's about to discover why an FBI agent like Ed Buckley was tasked with rooting out any connections between Chicago and militant Republicans. Dave's next moves will be in a city that goes as far as dyeing a whole river green on St. Patrick's Day. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Dave Rupert has spent years earning the trust of his IRA friends in Ireland and they've finally given him a military task. Dave heads back to Chicago with a name: Frank O'Neill. He's about to discover why an FBI agent like Ed Buckley was tasked with rooting out any connections between Chicago and militant Republicans. Dave's next moves will be in a city that goes as far as dyeing a whole river green on St. Patrick's Day.&nbsp; Learn more about your ad choices. Visit <a href="https://podcastchoices.com/adchoices" rel="noopener noreferrer">podcastchoices.com/adchoices</a>

S2 E06: The City That Dyes its River Green

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!

True Crime

History

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!

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S2 E06: The City That Dyes its River Green

S2 E06: The City That Dyes its River Green

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