In this compelling episode of Gangland Wire, retired Kansas City detective Gary Jenkins sits down with Kurt Calabrese, son of infamous Chicago Outfit enforcer Frank Calabrese Sr. Kurt opens up about what it was like growing up in the shadow of one of the most feared men in organized crime and living through the seismic fallout of the Family Secrets Trial.
Kurt shares a deeply personal account of his childhood in Elmwood Park, an Italian-American neighborhood where the surface was peaceful but the undercurrent ran dark. He recalls days spent playing sports and evenings surrounded by neighbors who seemed like family—but behind the closed doors of their three-flat home, fear and control ruled.
As the episode unfolds, Kurt discusses the moment he began to understand the truth about their father’s real occupation. Taught to lie and protect the family's image, they told classmates their dad was an engineer—masking a far more dangerous truth. The psychological burden of carrying this secret is a recurring theme in Kurt’s story.
Kurt paints a vivid picture of mob family dynamics, the juxtaposition of family life and violence, and the emotional toll of being raised by a man, he both feared and revered. He reveals the lasting impact of physical and emotional abuse at the hands of his father and how it contributed to his own diagnosis of complex PTSD.
Listeners will hear firsthand what living through the Family Secrets Trial was like, a landmark case that exposed the Chicago Outfit’s inner workings. Kurt Calabrese speaks candidly about the threats he and his family faced, the betrayal from his brother Frank Jr.’s cooperation with the FBI, and his complicated relationship with the truth, loyalty, and justice.
We also learn about Kurt’s marriage to Angela LaPietra—the granddaughter of another mob figure—and the intense family conflict that followed. From physical altercations with his father to the ripple effects on his children, Kurt doesn’t hold back. Click here for Kurt's website.
Finally, Kurt introduces his podcast, Underbelly: Killing Kurt, where he digs deeper into his story to expose the unseen scars left by a life entangled in organized crime.
This episode is an emotional and eye-opening exploration of how mob life impacts not just communities but also the families at its core. Kurt Calabrese is not just telling his story—he’s reclaiming it.
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[0:00] Well, hey, welcome all you wiretappers out there. It's good to be back here
[0:03] in the studio of Gangland Wire. I have a story today and an interview, as you can see. My interviewee is Kurt Calabrese. Now, Kurt Calabrese is from Chicago and he grew up in a Chicago outfit family. Now, a lot of you guys know, if you're real mob aficionados, you know about the Family Secrets Trial. And his father, Kurt's father, was Frank Calabrese Sr., his brother, Frank Calabrese Jr., who we had on the show several years ago. One of my earliest interviews, actually. And then his uncle, Nick Calabrese, ended up going to Witness Protection Program. And so that's why they called it the Family Secrets Trial, because it was all centered around the Calabrese family. So I really look forward to talking to Kurt. And Kurt, welcome.
[0:53] Thank you, Gary. Thank you for having me. So, Kurt, we talked a little bit before the show. And, you know,