Underbelly: Killing Kurt 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 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!

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!

 

#39

S3 E08: The Final Errand

In the final chapter of Killing Kurt, Kurt Calabrese travels to a remote house in North Ca... more

14 May 2025

48 MINS

48:14

14 May 2025


#38

S3 E07: I Will Be Praying For Your Soul

As Kurt Calabrese tries to settle into life after prison, ominous threats begin to arrive—... more

07 May 2025

42 MINS

42:47

07 May 2025


#37

S3 E06: Brotherly Love

In 1998, Frank Calabrese Jr. makes the most dangerous decision of his life: he writes a le... more

30 Apr 2025

41 MINS

41:34

30 Apr 2025


#36

S3 E05: The Letter

In 1995, the FBI's years-long investigation into the Chinatown crew comes to a head with s... more

23 Apr 2025

37 MINS

37:12

23 Apr 2025


#35

S3 E04: Take the Money and Run

A duffel bag filled with mob cash disappears—and with it, any remaining trust between Kurt... more

16 Apr 2025

35 MINS

35:42

16 Apr 2025


#34

S3 E03: Where Did Matt Go?

By the early 1990s, Frank Calabrese Sr. had spent decades building a criminal empire fuele... more

09 Apr 2025

43 MINS

43:03

09 Apr 2025


#33

S3 E02: The Man Is Nuts

The complicated relationship between Kurt Calabrese and his Uncle Nick reveals how Nick be... more

02 Apr 2025

42 MINS

42:21

02 Apr 2025


#32

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., b... more

02 Apr 2025

38 MINS

38:44

02 Apr 2025


#31

"Underbelly: Killing Kurt" Official Trailer - Premieres April 2nd!

For years, Kurt Calabrese lived under the violent rule of his father, feared Chicago hitma... more

12 Mar 2025

01 MINS

01:58

12 Mar 2025


#30

"The Rebel Kind" BONUS: An interview with David Rupert (Happy St. Patrick's Day!)

In advance of the Season 3 premiere of Underbelly on April 2nd, Entropy Media brings you a... more

17 Mar 2025

1 HR 17 MINS

1:17:06

17 Mar 2025


#29

Introducing "Game Plan: The Wendell Brown Story" - Out Now!

A special look at the trailer for "Game Plan: The Wendell Brown Story," the newest podcast... more

14 Aug 2024

01 MINS

01:50

14 Aug 2024


#28

S2 E12: The Other Side of Town

Dave Rupert retires to a life in hiding, reflecting on a journey that took him across the ... more

05 Jun 2024

41 MINS

41:49

05 Jun 2024


#27

S2 E11: McKevitt v. Pallasch

Dave Rupert's contract was just for intelligence gathering, but now he's asked to testify ... more

29 May 2024

52 MINS

52:31

29 May 2024


#26

S2 E10: Spying on Mickey

After years of hard work and learning the ins and outs of Irish republicanism, Dave Rupert... more

22 May 2024

37 MINS

37:02

22 May 2024


#25

S2 E09: The Two Mickeys

The last militant Republicans still willing to fight after the Omagh bombing are looking f... more

08 May 2024

42 MINS

42:26

08 May 2024


#24

S2 E08: Omagh

A car bomb explosion kills 31 people -- including unborn twins -- in the town center of Om... more

01 May 2024

44 MINS

44:19

01 May 2024


#23

S2 E07: Good Friday

On Good Friday in 1998, a treaty that will come to be called the Good Friday Agreement is ... more

24 Apr 2024

43 MINS

43:07

24 Apr 2024


#22

S2 E06: The City That Dyes its River Green

Dave Rupert has spent years earning the trust of his IRA friends in Ireland and they've fi... more

17 Apr 2024

46 MINS

46:08

17 Apr 2024


#21

S2 E05: Coin Operated

A visit to Dave's family in upstate New York gets Bob and Abdon a history lesson on Joe Be... more

10 Apr 2024

50 MINS

50:52

10 Apr 2024