Underbelly
Entropy Media
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 offici...
Episode list
21
April 16, 2025
35 min
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.Ku...
moreApril 9, 2025
43 min
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 ...
moreApril 2, 2025
38 min
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 en...
moreApril 2, 2025
42 min
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...
moreMarch 17, 2025
1 hr 17 min
"The Rebel Kind" BONUS: An interview with David Rupert (Happy St. Patrick's Day!)
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...
moreMarch 12, 2025
1 min
"Underbelly: Killing Kurt" Official Trailer - Premieres April 2nd!
For years, Kurt Calabrese lived under the violent rule of his father, feared Chicago hitman Frank “The Breeze” Calabrese Sr. But when his brother turned informant, their family—and...
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