Underbelly

About Underbelly

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!

Publisher

Entropy Media

Category

history · true crime

Language

en

Explicit

Yes

First episode

4 Apr 2023

Latest episode

14 May 2025

Latest episodes

25 of 40 episodes have a transcript.

1. 

   14 May 2025TRANSCRIPT

   S3 E08: The Final Errand

   Kurt Calabrese confronts the body of his abusive father, Frank Calabrese Sr., in a remote house, seeking closure amidst the unraveling of their criminal empire as federal agents uncover hidden evidence.

2. 

   7 May 2025TRANSCRIPT

   S3 E07: I Will Be Praying For Your Soul

   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

3. 

   30 Apr 2025TRANSCRIPT

   S3 E06: Brotherly Love

   Frank Calabrese Jr. risks his life by turning against his mob enforcer father, initiating an audacious undercover operation within federal prison to dismantle their family's criminal empire and provide evidence for the Family Secrets case; this is an investigative episode.

Inside a recent episode

S3 E08: The Final Errand

Published 14 May 2025 · Transcript excerpt

[…] In addition to cash, the agents found almost $2 million worth of diamonds, along with some guns and audio tapes. The rating of Frank's home symbolized the end of his reign of terror, and it was also reflective of what was happening to the outfit as an organization. Here's a CBS News Special from 2019 detailing the fallout of the family's secrets trial. Frank Calibri's junior was the main witness in the landmark FBI investigation called Family Secrets. It helped authorities solve nearly 20 mob murders going back to 1970. Frank Calibri's senior was sentenced to life in prison. Jail, gang land hits, constant government surveillance. […]

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

14,408

Score snapshot 15 Sept 2025

Apple Podcasts (US)

4.9 / 5

293 ratings

Spotify

4.9 / 5

244 ratings

Podcast Authority Score: 44 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

17

Social presence

0

YouTube

76

Engagement

99

Shows with a similar audience

• 

  The Underworld Podcast

• 

  In The Dark

• 

  Gangland Wire

• 

  What Happened to the McStays?

• 

  Beyond All Repair

• 

  Reaching Out