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 ol
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Booking probability
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Guest openness
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Signup to Generate a PitchFor 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.
Recent episodes include "S3 E08: The Final Errand" (14 May 2025, 44 minutes), "S3 E07: I Will Be Praying For Your Soul" (7 May 2025, 39 minutes), and "S3 E06: Brotherly Love" (30 April 2025, 37 minutes).
Underbelly: Killing Kurt publishes roughly weekly, with episodes averaging 38 minutes across 39 episodes.
Booking probability for Underbelly: Killing Kurt is 32%, and the host is rated Selective on guests. Underbelly: Killing Kurt requires a Pod Score of 80 or higher. Underbelly: Killing Kurt's contact route on record: verified email.
Underbelly: Killing Kurt is a history podcast with 39 episodes published.
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Episode #8
<p>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...
Episode #7
<p>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...
Episode #6
<p>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...
Episode #5
<p>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...
Episode #4
<p>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.</p><p><br></p><p>Kurt’s loyalty is...
Episode #3
<p>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...
Episode #2
<p>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...
Episode #1
<p>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...
Underbelly: Killing Kurt
<p>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...
Underbelly: Killing Kurt
<p>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...
Underbelly: Killing Kurt
<p>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)</p><p><br></p><p>Synopsis: After his pro football career...
Episode #12
<p>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...
Episode #11
<p>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...
Episode #10
<p>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...
Episode #9
<p>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...
Episode #8
<p>A car bomb explosion kills 31 people -- including unborn twins -- in the town center of Omagh in Northern Ireland. The Real IRA takes public responsibility for the bombing, but the story that trickles out maintains...
Episode #7
<p>On Good Friday in 1998, a treaty that will come to be called the Good Friday Agreement is signed by several nations. At its core, it's an a plan for peace that will involve a decommissioning process for paramilitary...
Episode #6
<p>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...
Episode #5
<p>A visit to Dave's family in upstate New York gets Bob and Abdon a history lesson on Joe Beef, Joby for short. That was Dave's nickname growing up in rural Madrid and it stuck with his family through his litany of...
Episode #4
<p>Dave's plot to run a bar for profit while spying on vacationing republicans along the banks of the Drowes River is a rocky as the road to Dublin. The former owner of his pub wasn't paying the bills and that makes...
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