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!
All content for Underbelly: Killing Kurt is the property of Entropy Media and is served directly from their servers
with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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!
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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Underbelly: Killing Kurt
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!
