Underbelly: Killing Kurt

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

As Kurt Calabrese tries to settle into life after prison, ominous threats begin to arrive—dead rats on his porch, anonymous letters, and a staged bomb at his home—signs someone in the Outfit suspects he’s cooperating with the Feds. While he denies involvement, suspicion falls on his father and the father's girlfriend, Diane, whose presence near Kurt’s home the night of the rat incident raises red flags. The threats escalate just as the landmark Operation Family Secrets trial kicks off, charging multiple high-ranking Chicago mobsters with 18 murders. It’s a case built on unprecedented betrayal, with mob sons turning on their fathers—and Kurt caught in the crossfire of a family and a criminal empire coming undone. 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

In 1998, Frank Calabrese Jr. makes the most dangerous decision of his life: he writes a letter to the FBI offering to turn against his own father—one of the most feared mob enforcers in Chicago history. What follows is one of the most audacious undercover operations in the history of organized crime. In this episode, we go inside the moment that changed everything for the Calabrese family and the Chicago Outfit. After being transferred to the same prison as his father, Junior realizes the only way to escape is to cooperate. He offers to wear a wire inside federal prison, hoping to capture Frank Calabrese Sr. incriminating himself in decades of unsolved mob murders. Told through secret recordings, FBI testimony, and Junior’s own words, this is the story of how one son risked his life to dismantle the family empire he was born into. It’s also the origin of the evidence that would form the heart of the Family Secrets case—the case that brought down the Outfit. 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

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! Learn more about your ad choices. Visit podcastchoices.com/adchoices

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! Learn more about your ad choices. Visit podcastchoices.com/adchoices