chicago outfit Archives - Gangland Wire

Chicago Outfit Informants

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In this episode, we delve into the intricate world of the Chicago Outfit’s informants, featuring insights from my late friend, Cam Robinson, and Paul Whitcomb, a well-respected expert on the mob. This special compilation draws from past interviews and shorts that once highlighted various informants who operated during the notorious 1980s era of organized crime […]

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Bob Cooley and the Deadliest Man Alive

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In this special short episode of Gangland Wire, Gary Jenkins presents a wild and largely forgotten chapter from Bob Cooley’s life—the former Chicago Outfit fixer, gambler, and lawyer whose career straddled the worlds of organized crime, corruption, and courtroom drama. Fresh off a long-form interview with Cooley, Gary pulls out a standalone story that feels

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Bob Cooley Outfit Chief Fixer Part 1

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In this gripping episode of Gangland Wire, host Gary Jenkins sits down with Robert “Bob” Cooley, the Chicago lawyer whose extraordinary journey took him from deep inside the Outfit’s criminal operations to becoming one of the federal government’s most valuable witnesses against organized crime. Cooley pulls back the curtain on the hidden machinery of Chicago’s

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Chuck Goudie talks Chicago Outfit

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In this episode of Gangland Wire, retired Kansas City Intelligence detective Gary Jenkins sits down with veteran Chicago journalist Chuck Goudie, whose decades of reporting have made him one of Chicago’s most respected voices on organized crime. A fan of the show asked for more Chicago stories—and this conversation delivers. We dive into the legacy

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Behind the Walls: Dave Grosky on Life inside with Chicago’s Jerry Scalise

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In this revealing episode of Gangland Wire, retired intelligence detective Gary Jenkins sits down with Dave Grosky, a man who spent over a decade inside federal prisons—and came out with a story unlike any other. From FCI Loretto to Morgantown to Milan, Dave’s journey through the prison system introduced him to a cast of characters

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Inside a Chicago Mob Family with Kurt Calabrese

Leave a Comment / Gangland Wire Crime Stories / Gary Jenkins

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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

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The Mob and Rock and Roll

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Retired Intelligence Detective Gary Jenkins brings you the best in mob history with his unique perception of the mafia. In this episode of Gangland Wire, host Gary Jenkins interviews the prolific chronicler of the American Mafia, Jeffrey Sussman. Listeners will learn about Morris levy and the mafia’s influence on the roots of the world’s most

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The Sadistic Reign of Mad Sam DeStefano

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In this episode, Gary takes a deep dive into the ruthless life of Mad Sam DeStefano, one of the most brutal enforcers in organized crime history. A notorious loan shark tied to the Chicago Outfit, DeStefano’s reputation for violence and torture made him a feared figure—even among his fellow mobsters. Born in 1909 in Illinois,

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Ken Eto and the Chicago Outfit

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Ken Eto or Tokyo Joe was an unusual dude in the world of the Sicilian Chicago Outfit. The only Japanese American to be in any position of trust with the Chicago Outfit or any other family. He was Japanese-American born in 1919. In 1942 the feds placed his entire family in a Japanese Internment Camp.

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Anatomy of an Outfit Murder

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When researching organized crime murders, sometimes there are clues that tip us off to what may have really happened. We recently discussed the Wild Bunch, a crew of Chicago Outfit hitmen in the 1970s, and that touched back to an earlier series on Wild Bunch member and notorious killer Harry “The Hook” Aleman. Let’s look

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