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Artwork for Underbelly: Killing Kurt

Underbelly: Killing Kurt

Entropy Media
IRA
Good Friday Agreement
Omagh Bombing
Northern Ireland
Irish Republican Army
FBI
Mickey Mckevitt
Northern Ireland Conflict
Frank Calabrese Sr.
Chicago
Wendell Brown
Chicago Outfit
Dave Rupert
Family Secrets Trial
Kurt Calabrese
Michael Gallagher
Chinese Prison System
Real IRA
Irish Republicanism
MI5

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 terr... more

PublishesWeeklyEpisodes53Founded3 years ago
Categories
HistoryTrue Crime

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Artwork for Underbelly: Killing Kurt

Latest Episodes

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 ... more

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 in... more

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 under... more

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 t... more

Key Facts

Accepts Guests
Accepts Sponsors
Contact Information
Podcast Host

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Recent Guests

Kurt Calabrese
Son of Frank Calabrese Sr., reflecting on his family’s turbulent history in the Chicago Outfit.
Episode: S3 E08: The Final Errand
Junior Calabrese
Kurt's brother who struggled with addiction and involvement in crime
Episode: S3 E04: Take the Money and Run
Frank The Breeze Calabrese
Infamous Chicago mobster and father of Kurt and Junior
Episode: S3 E04: Take the Money and Run
Thomas Bourgeois
Retired FBI agent
Episode: S3 E03: Where Did Matt Go?
Matt Russo
Auto shop owner heavily involved in the mob's operations
Episode: S3 E03: Where Did Matt Go?
Kent Ito
Mob sleeper boss and informant
Episode: S3 E03: Where Did Matt Go?
Joe R. Lopez
Legendary Chicago defense attorney who represented Frank Calabrese Sr during the Family Secrets trial.
Law Firm
Episode: S3 E01: I'll Kick You So Hard You'll Walk Funny
Damon Charonis
Chicago defense attorney who represented one of Frank's co-defendants in the Family Secrets trial.
Law Firm
Episode: S3 E01: I'll Kick You So Hard You'll Walk Funny
Marcus Funk
Federal prosecutor involved in the Family Secrets case.
Federal Government
Episode: S3 E01: I'll Kick You So Hard You'll Walk Funny

Host

Anjay Nagpal
Host providing insights into the narratives explored in the series and guiding the storytelling processes.

Reviews

4.9 out of 5 stars from 512 ratings
  • Beautiful

    Beautiful beginning and a beautiful ending (of the podcast). However, Kurt you are one wonderful person and father and you have done as best as you could with zero guidance. God bless❤️

    Apple Podcasts
    5
    Omahabyrd
    United States5 months ago
  • Kurt Calabrese, we love you.

    You are a truly honorable man Kurt. I believe he DID in fact mean every bit of that letter. Please take care Kurt.

    Apple Podcasts
    5
    Midwest Original
    United States5 months ago
  • Season2

    Just finished season 2 , what an incredible story. I learned so much about Irish history!

    Apple Podcasts
    5
    JanefromNj
    United States5 months ago
  • 3rd & final I’m sorry if I’m becoming a pain

    One last thing Kurt even though we’ve never met but I feel as if I know you never forget Kurt you have people you don’t even know love you, care about you, and have the ultimate respect for you!!

    Apple Podcasts
    5
    my windy city
    United States6 months ago
  • Love this show!

    Growing up in chicago I know these places and accents. Such a great story that captures the specificity of the chicago finance scene. Fabulous characters.

    Apple Podcasts
    5
    PDXHamsterCat
    United Statesa year ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

The production quality and storytelling style have been praised, making complex themes accessible and entertaining, while others appreciate the psychological exploration within the criminal context.
Many reviews note the powerful narrative that intertwines personal struggles with the history of organized crime, offering unique insights that keep audiences invested throughout the series.
Listeners commend the podcast for its engaging storytelling and emotional depth, highlighting Kurt’s authenticity and relatable experiences.

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Talking Points

Recent interactions between the hosts and their guests.

S3 E08: The Final Errand
Q: Do you think there's any way in his, any change in his own way that he loved you?
Kurt reflects on a letter from his father, realizing that it might indicate his father's love and acknowledgment, even amidst their troubled relationship.
"The Rebel Kind" BONUS: An interview with David Rupert (Happy St. Patrick's Day!)
Q: What would you want people to know about you, you know, who you are, you know, what you did?
He reflects on his experiences in the IRA and how they contributed to saving the peace process in Ireland, emphasizing his belief in pacifism.
"The Rebel Kind" BONUS: An interview with David Rupert (Happy St. Patrick's Day!)
Q: Could you recount the story about the guy that threatened you?
Rupert recounts a tense exchange with a passenger who threatened him, highlighting how he managed the situation calmly.
"The Rebel Kind" BONUS: An interview with David Rupert (Happy St. Patrick's Day!)
Q: Tell us in the short version, why did, how did you come to be driving an Uber?
Rupert explains that Uber provides an easy way to make extra cash, especially given his past experiences and notoriety.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Gender Skew
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Social Media Reach

Frequently Asked Questions About Underbelly: Killing Kurt

What is Underbelly: Killing Kurt about and what kind of topics does it cover?

This podcast provides a compelling narrative centered around the life of Kurt Calabrese, whose childhood was shaped by the violent and controlling nature of his father, Frank "The Breeze" Calabrese Sr., a notorious figure within the Chicago Outfit. Through a series of personal reflections and vivid storytelling, listeners are granted an intimate look at the psychological impact of growing up in a mob family marked by betrayal, loyalty, and the struggle for survival. Each episode navigates the complexities of familial relationships against the backdrop of the infamous Family Secrets Trial, which exposed numerous unsolved murders and criminal operations tied to the Chicago mob.

What makes this podcast distinct is its blend of true crime with... more

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Which podcasts are similar to Underbelly: Killing Kurt?

These podcasts share a similar audience with Underbelly: Killing Kurt:

1. The Underworld Podcast
2. Gangland Wire
3. The Sit Down: A Crime History Podcast
4. Bone Valley
5. American Scandal

How many episodes of Underbelly: Killing Kurt are there?

Underbelly: Killing Kurt launched 3 years ago and published 53 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Underbelly: Killing Kurt?

Recent guests on Underbelly: Killing Kurt include:

1. Kurt Calabrese
2. Junior Calabrese
3. Frank The Breeze Calabrese
4. Thomas Bourgeois
5. Matt Russo
6. Kent Ito
7. Joe R. Lopez
8. Damon Charonis

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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