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 <a href="https://podcasts.apple.com/us/channel/entropy-media/id6503914400">⁠⁠HERE ⁠⁠</a>to learn more! Learn more about your ad choices. Visit <a href="https://podcastchoices.com/adchoices">podcastchoices.com/adchoices</a>

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

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 <a href="https://podcasts.apple.com/us/channel/entropy-media/id6503914400" rel="noopener noreferrer">⁠⁠HERE ⁠⁠</a>to learn more! Learn more about your ad choices. Visit <a href="https://podcastchoices.com/adchoices" rel="noopener noreferrer">podcastchoices.com/adchoices</a>

S3 E07: I Will Be Praying For Your Soul

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!

True Crime

History

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!

Share S3 E07: I Will Be Praying For Your Soul

Sign up to save your podcasts

S3 E07: I Will Be Praying For Your Soul

S3 E07: I Will Be Praying For Your Soul

More shows like Underbelly: Killing Kurt

Stuff You Should Know

Criminal

WTF with Marc Maron Podcast

20/20

48 Hours

Buried Bones - a historical true crime podcast with Kate Winkler Dawson and Paul Holes

Dateline NBC

America's Crime Lab

The Binge Cases: Where is Daniel Morcombe?

The Underworld Podcast

The Sit Down: A Crime History Podcast

Bone Valley

Game Plan: The Wendell Brown Story

Fifteen: Inside the Daniel Marsh Murders

Deadly Engagement