Bob Cooley Outfit Fixer Part 2 Titelbild

Bob Cooley Outfit Fixer Part 2

Bob Cooley Outfit Fixer Part 2

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 In this episode of Gangland Wire, Gary Jenkins sits down with Bob Cooley, the once–well-connected Chicago lawyer who lived at the center of the city’s most notorious corruption machine. After years out of the public eye, Cooley recently resurfaced to revisit his explosive memoir, When Corruption Was King—and this conversation offers a rare, firsthand look at how organized crime, politics, and the court system intersected in Chicago for decades. Cooley traces his journey from growing up in a police family to serving as a Chicago police officer and ultimately becoming a criminal defense attorney whose real job was quietly fixing cases for the Chicago Outfit. His deep understanding of the judicial system made him indispensable to mob-connected power brokers like Pat Marcy, a political fixer with direct access to judges, prosecutors, and court clerks. Inside the Chicago Corruption Machine Cooley explains how verdicts were bought, cases were steered, and justice was manipulated—what insiders called the “Chicago Method.” He describes his relationships with key figures in organized crime, including gambling bosses like Marco D’Amico and violent enforcers such as Harry Aleman and Tony Spilotro, painting a chilling picture of life inside a world where loyalty was enforced by fear. As his role deepened, so did the psychological toll. Cooley recounts living under constant threat, including a contract placed on his life after he refused to betray a fellow associate—an event that forced him to confront the cost of the life he was leading. Turning Point: Becoming a Federal Witness The episode covers Cooley’s pivotal decision in 1986 to cooperate with federal authorities, a move that helped dismantle powerful corruption networks through FBI Operation Gambat. Cooley breaks down how political connections—not just street-level violence—allowed the Outfit to operate with near-total impunity for so long. Along the way, Cooley reflects on the moral reckoning that led him to turn on the system that had enriched and protected him, framing his story as one not just of crime and betrayal, but of reckoning and redemption. What Listeners Will Hear How Bob Cooley became the Outfit’s go-to case fixer The role of Pat Marcy and political corruption in Chicago courts Firsthand stories involving Marco D’Amico, Harry Aleman, and Tony Spilotro The emotional and psychological strain of living among violent criminals The decision to cooperate and the impact of Operation Gambat Why Cooley believes Chicago’s corruption endured for generations Why This Episode Matters Bob Cooley is one of the few people who saw the Chicago Outfit from inside the courtroom and the back rooms of power. His story reveals how deeply organized crime embedded itself into the institutions meant to uphold the law—and what it cost those who tried to escape it. This episode sets the stage for a deeper follow-up conversation, where Gary and Cooley will continue unpacking the most dangerous and revealing moments of his life. Resources Book: When Corruption Was King by Bob Cooley Hit me up on Venmo for a cup of coffee or a shot and a beer @ganglandwire Click here to “buy me a cup of coffee” Subscribe to the website for weekly notifications about updates and other Mob information. To go to the store or make a donation or rent Ballot Theft: Burglary, Murder, Coverup, click here To rent ‘Brothers against Brothers’ or ‘Gangland Wire,’ the documentaries click here. To purchase one of my books, click here. 0:03 Prelude to Bob Cooley’s Story 1:57 Bob Cooley’s Background 5:24 The Chicago Outfit Connection 8:24 The Turning Point 15:20 The Rise of a Mob Lawyer 23:54 A Life of Crime and Consequences 26:03 The Incident at the Police Station 50:27 The Count and His Influence 1:19:51 The Murder of a Friend 1:35:26 Contracts and Betrayal 1:40:36 Conclusion and Future Stories Transcript [0:00] Well, hey guys, this is a little prelude to my next story. Bob Cooley was a Chicago lawyer and an outfit associate who had been in, who has been in hiding for many years. I contacted him about six or seven years ago when I first started a podcast, I was able to get a phone number on him and, and got him on the phone. He was, I think it was out in the desert in Las Vegas area at the time. And at the time he was trying to sell his book when corruption was king to a movie producer And he really didn’t want to overexpose himself, and they didn’t really want him to do anything. And eventually, COVID hit, and the movie production was canceled. And it was just all over. There were several movie productions were canceled during COVID, if I remember right. A couple people who I have interviewed and had a movie deal going. Well, Bob recently remembered me, and he contacted me. He just called me out of the clear blue, and he wanted to revive his book and his story. He’s been, you know, way out of the limelight for a long time. And so I ...
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