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Deep Cover

Introducing Underbelly: Killing Kurt

Mon, 28 Apr 2025

Description

We’re sharing a trailer from season three of the Underbelly podcast: Killing Kurt. Kurt Calabrese grew up in the shadow of his father, Frank “The Breeze” Calabrese Sr., a feared hitman for the Chicago Outfit. In a home ruled by violence and paranoia, loyalty wasn’t a choice... it was survival. Then came the Family Secrets Trial, exposing 18 unsolved murders and tearing the mob apart. But before the headlines, the real story started inside the Calabrese family. This season on Underbelly: Killing Kurt, Kurt Calabrese shares his story of the betrayal that took down his father, the violence at home, and the cost of growing up in the mob. From Entropy Media, listen to Underbelly: Killing Kurt. Available now wherever you get your podcasts.See omnystudio.com/listener for privacy information.

Audio
Transcription

Chapter 1: What is the focus of Underbelly: Killing Kurt?

6.328 - 14.274 Narrator

Pushkin. Take a listen, and if you want to hear more, Underbelly Killing Kurt is now available wherever you listen to podcasts.

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Chapter 2: What was the Family Secrets Trial?

34.952 - 48.061 John Smith

In Chicago, one of the biggest mafia trials in years began today. And the name says it all. The Family Secrets Trial. These were almost like movie characters who were going to be on trial in the real world, in federal court.

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Chapter 3: How did the Family Secrets Trial impact the Chicago Outfit?

48.381 - 56.207 Narrator

So you had people lining up to see it. The legacy of this trial was the end of the Chicago outfit as we knew it. It ended right then and there.

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Chapter 4: Who is Frank 'The Breeze' Calabrese?

57.15 - 68.173 Narrator

In season three of Entropy's Underbelly franchise, we're shedding new light on a family drama so intense, it led to an infamous mob trial. And it all started with one man.

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Chapter 5: What led to the infamous mob trial?

68.673 - 76.776 John Smith

Frank the Breeze Calabrese, longtime enforcer of the feared Chinatown crew. He would beat people, strangle them, and then slit their throats. That was sort of his calling card.

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77.616 - 83.938 Narrator

This man, Frank Calabrese Sr., terrorized everyone, including his two sons.

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84.875 - 91.539 Kurt Calabrese

And his father turned him around and put a revolver in his cheek and said, I would rather have you dead than disobey me.

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92.179 - 122.069 Narrator

Fearing death, one of the Calabrese sons went to the FBI to help them put his father away for good. The other son, Kurt, was in the middle of it all. And he says there is a lot the public still doesn't know. But for years, he's kept it buried and it almost killed him. Now, finally, Kurt Calabrese is telling his story. There was conservatively a million and a half to two million dollars there.

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122.089 - 138.039 Narrator

The phone started ringing, and it was the FBI. When he finds out this money's gone, he's gonna hurt me too. You can listen to Underbelly season three, Killing Kurt, from Entropy Media, wherever you listen to podcasts.

139.059 - 145.736 Kurt Calabrese

And he took his whole family down with him, And I call it the family that destroyed the family.

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