In 1995, the FBI's years-long investigation into the Chinatown crew comes to a head with sweeping indictments and early morning raids. With their criminal empire crumbling, the Calabrese family faces the full weight of the justice system—and begins to turn on itself.
This episode tells the harrowing story of what happens when loyalty becomes a liability. Junior faces a 30-year prison sentence. Kurt is offered a deal: serve two years, and his brother, father, and uncle all get reduced sentences. Despite a lifetime of abuse at the hands of his father, Kurt agrees—sacrificing his own freedom for the sake of family.
But even behind bars, Frank “The Breeze” Calabrese Sr. remains in control—cutting financial support to his sons’ families and manipulating Kurt into continuing the family’s illicit business. With a handshake deal and no paperwork to protect his loved ones, Kurt finds himself once again used by the man he trusted least.
As prison walls close in, and brother turns against brother, Kurt reflects on what it truly means to make a deal with the devil—and what’s left when the devil doesn’t keep his end.
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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37:12
S3 E04: Take the Money and Run
A duffel bag filled with mob cash disappears—and with it, any remaining trust between Kurt Calabrese, his brother Junior, and their volatile father, Frank “The Breeze” Calabrese.
Kurt’s loyalty is tested like never before when his father shows up unannounced, ready to retrieve what he believes is still safely hidden in the bank. But when Frank discovers the money is gone, suspicion quickly turns to rage—and all roads lead to Junior. What follows is a brutal confrontation on a suburban lawn, a devastating confession, and the unraveling of a family already under intense FBI surveillance.
As Frank becomes more unhinged, Kurt is pulled deeper into his father's dangerous world, forced to collect debts and even contemplate arson—pushed to the brink of committing crimes he never wanted to be a part of. Meanwhile, Junior’s decisions spiral out of control, dragging friends, businesses, and his own freedom into the fallout.
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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35:42
S3 E03: Where Did Matt Go?
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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43:03
S3 E02: The Man Is Nuts
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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42:21
S3 E01: I'll Kick You So Hard You'll Walk Funny
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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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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