"The Rebel Kind" BONUS: An interview with David Rupert (Happy St. Patrick's Day!)
Underbelly: Killing KurtShow Notes
In advance of the Season 3 premiere of Underbelly on April 2nd, Entropy Media brings you a special BONUS episode of The Rebel Kind in honor of St. Patrick’s Day—a story deeply tied to Ireland’s turbulent past and one man’s extraordinary role in shaping its future.
For the first time ever, David Rupert—the trucker-turned-international-informant who helped take down Real IRA leader Mickey McKevitt—breaks his silence in a rare and candid interview. After spending years in witness protection, David reached out upon hearing Underbelly: The Rebel Kind and agreed to sit down with Abdon Pallasch and Bob Herguth, the journalists who first documented his extraordinary story. In this special bonus episode, David reflects on his double life, the high-stakes world of counterterrorism, and the personal cost of his undercover work. He also reveals what it’s like to live off the grid—and shares some jaw-dropping stories you won’t hear anywhere else.
Listen now, and for more exclusive content from Underbelly and other Entropy Media podcasts, subscribe to Entropy Unlimited on Apple Podcasts. And don’t miss the Season 3 premiere of Underbelly: Killing Kurt, on April 2nd. Learn more about your ad choices. Visit podcastchoices.com/adchoices
More from Underbelly: Killing Kurt
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 to face with the body of Frank Calabrese Sr.—the man who dominated, abused, and haunted his life. For the first time, Kurt is able to speak freely to his father, unleashing years of pain, rage, and conflicted love.
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.
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 undercover operations in the history of organized crime.
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 to turn on itself. This episode tells the harrowing story of what happens when loyalty becomes a liability. Junior faces a 30-year prison sentence. Kurt is offered a deal: serve two years, and his brother, father, and uncle all get reduced sentences. Despite a lifetime of abuse at the hands of his father, Kurt agrees—sacrificing his own freedom for the sake of family.
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.