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PODCAST

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

true crime

All Episodes

48:14

S3 E08: The Final Errand

Underbelly: Killing Kurt ·

2025/05/14

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

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42:47

S3 E07: I Will Be Praying For Your Soul

Underbelly: Killing Kurt ·

2025/05/07

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

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41:34

S3 E06: Brotherly Love

Underbelly: Killing Kurt ·

2025/04/30

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

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37:12

S3 E05: The Letter

Underbelly: Killing Kurt ·

2025/04/23

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

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35:42

S3 E04: Take the Money and Run

Underbelly: Killing Kurt ·

2025/04/16

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

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43:03

S3 E03: Where Did Matt Go?

Underbelly: Killing Kurt ·

2025/04/09

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

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38:44

S3 E01: I'll Kick You So Hard You'll Walk Funny

Underbelly: Killing Kurt ·

2025/04/02

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

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42:21

S3 E02: The Man Is Nuts

Underbelly: Killing Kurt ·

2025/04/02

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

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77:06

"The Rebel Kind" BONUS: An interview with David...

Underbelly: Killing Kurt ·

2025/03/17

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 man’s extraordinary role in shaping its future.For the first time ever, David Rupert—the trucker-turned-international-informant who helped take down Real IRA leader Mickey McKevitt—breaks his silence in a rare and candid interview. After spending years in witness protection, David

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1:58

"Underbelly: Killing Kurt" Official Trailer -...

Underbelly: Killing Kurt ·

2025/03/12

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 apart. The betrayal led to a historic trial, exposing decades of unsolved murders and taking down some of the most powerful mob figures in modern history. But behind the headlines was an even darker story—one of family loyalty, fear, and survival. Now, for the first time, Kurt reveals

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1:50

Introducing "Game Plan: The Wendell Brown Story" -...

Underbelly: Killing Kurt ·

2024/08/14

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)Synopsis: After his pro football career ended, college star Wendell Brown moved to China to teach his beloved sport to youth abroad. But when the Detroit legend is assaulted at a 2016 party in the Yuzhong District, he’s the one charged with a crime. With little hope of being released by a court boasting a 99% conviction rate, Wendell must survive

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38:49

S2 E12: The Other Side of Town

Underbelly: Killing Kurt ·

2024/06/05

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 contributed to the peace in Ireland and whether a reunited Ireland could be possible in our lifetime. Learn more about your ad choices. Visit megaphone.fm/adchoices

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43:16

S2 E11: McKevitt v. Pallasch

Underbelly: Killing Kurt ·

2024/05/29

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 McKevitt faces charges under a new law in the Irish Special Criminal Court, his lawyers are going to have to dig deep to discredit a potential witness. That's when they get wind of a book deal back in Chicago. Learn more about your ad choices. Visit megaphone.fm/adchoices

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37:02

S2 E10: Spying on Mickey

Underbelly: Killing Kurt ·

2024/05/22

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 man who Irish and British governments say is the terrorist who must be stopped to prevent another tragedy like Omagh. Dave knows how to work his angles, but he worries about whether the security services can keep up. Learn more about your ad choices. Visit megaphone.fm/adchoices

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42:26

S2 E09: The Two Mickeys

Underbelly: Killing Kurt ·

2024/05/08

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? Joe O'Neil introduces Dave Rupert to a storied Republican named Mickey Donnelly and with that connection, Dave is whisked off to a meeting with the Real IRA's top man: Mickey McKevitt. Learn more about your ad choices. Visit megaphone.fm/adchoices

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44:19

S2 E08: Omagh

Underbelly: Killing Kurt ·

2024/05/01

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 it was a horrible mistake. In this episode, we explore the aftermath of the bombing that infuriated Irish from coast to coast, north and south. Meanwhile, Dave Rupert is suddenly in real danger as any IRA associates become public enemies and a central target of security services. Learn

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43:07

S2 E07: Good Friday

Underbelly: Killing Kurt ·

2024/04/24

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 groups and a plan for a future vote on a united Ireland. For some, it's about forgiveness, hope and peace. For others, it's the same old story: another surrender to British Authority. Dave Rupert has a front row seat for the final significant fracturing of militant Republicans of the

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46:08

S2 E06 The City That Dyes its River Green

Underbelly: Killing Kurt ·

2024/04/17

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 megaphone.fm/adchoices

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50:52

S2 E05: Coin Operated

Underbelly: Killing Kurt ·

2024/04/10

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 careers. Even through late 1997 when Dave inks his first official contract to become a spy -- affording him the opportunity to finally focus on the danger in militant republican circles. Learn more about your ad choices. Visit megaphone.fm/adchoices

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46:10

S2 E04: It's a Funny Place, Tullaghan

Underbelly: Killing Kurt ·

2024/04/03

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 Dave's life even more difficult. But a diligent barkeep certainly doesn't look like a spy and his plan kind of begins to work. Knowing the history of the British occupation in Ireland is just the tip of the iceberg for Dave's education on republican ideals. Learn more about your ad

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