Underbelly: Killing Kurt9 Apr 2025

S3 E03: Where Did Matt Go?

By the early 1990s, Frank Calabrese Sr. had spent decades building a criminal empire fueled by fear, paranoia, and control. He taught his sons the art of survival in the mob—never use house phones, memorize payphone numbers, speak in code, and trust no one. But when Frank let his guard down for an indebted auto shop owner named Matt Russo, the cracks in his armor started to show. What Frank saw as an opportunity to exploit a failing business, the FBI saw as the perfect way in. Russo, drowning in debt and desperate, became a federal informant and began wearing a wire in Frank’s inner circle. But gathering evidence on a man as cautious—and dangerous—as Frank Calabrese wouldn’t be easy. We go inside the FBI’s high-stakes operation to take Frank down, the meticulous way Frank shielded himself from betrayal, and the moment it all started to unravel. 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

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Episoder(39)

S3 E08: The Final Errand

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...

14 Mai 202544min

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 ...

7 Mai 202538min

S3 E06: Brotherly Love

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 histor...

30 Apr 202536min

S3 E05: The Letter

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 ...

23 Apr 202533min

S3 E04: Take the Money and Run

A duffel bag filled with mob cash disappears—and with it, any remaining trust between Kurt Calabrese, his brother Junior, and their volatile father, Frank “The Breeze” Calabrese. Kurt’s loyalty is te...

16 Apr 202531min

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., breaks his silence about growing up under the shadow of one of Chicago's most feared mob enforcers. His story b...

2 Apr 202534min

S3 E02: The Man Is Nuts

The complicated relationship between Kurt Calabrese and his Uncle Nick reveals how Nick became a surrogate father figure in Kurt's turbulent childhood. While Kurt's father Frank Sr. ruled through fear...

2 Apr 202538min