Bob Cooley Outfit Chief Fixer Part 1 from Gangland Wire

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Gary Jenkins: Mafia Detective

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Bob Cooley Outfit Chief Fixer Part 1

1 seconds Posted Dec 22, 2025 at 10:00 am.

Introduction to Bob Cooley

Life as an Outfit Gambler

My Relationship with Marco D'Amico

The Story of Hal Smith

A Dangerous Encounter

Meeting Sally D

A Contract on My Life

The Harry Alleman Case

Inside the Courtroom

The Verdict

Warning the Judge

The Case Against the Policewoman

Navigating the Legal Maze

The Outcome and Its Consequences

The Decision to Flip

A Father's Influence

The Corruption Revealed

Political Connections

The Setup for Robbery

Consequences of Loyalty

] Hey, guys, my guest today is a former Chicago outfit associate named Robert Bob Cooley. He has a book out there titled When Corruption Was King. I highly recommend you get it if you want to look inside the Chicago outfit of the 1970s. Now, Bob's going to tell us about his life as an outfit gambler, lawyer, and I use payoff to judges to get many, many not guilty verdicts. Now, I always call this the Chicago method. This happened for, I know, for Harry Ailman, a case we're going to talk about, Tony Spolatro got one of these not-guilties. Now, the outfit member associate who is blessed to get this fix put in for him may be charged with a crime, even up to murder. And he gets a lawyer, a connected lawyer, and they'll demand a bench trial. That means that only a judge makes the decision. A lawyer, like my guest, who worked with a political fixer named Pat Marcy.

] They'll work together and they'll get a friendly judge assigned to that case and then they'll bribe the judge. And all that judge needs is some kind of alibi witnesses and any kind of information to discredit any prosecution witnesses. Now, this is back in the olden days before you had all this DNA and all that kind of thing. So physical evidence was not really a part of it. Mainly, it was from witnesses. And they just have to discredit any prosecution witness. Then the judge can say, well, state hadn't really proven their case beyond a reasonable doubt and issue a not guilty verdict and walk away. Now, our guest, Bob Cooley, is going to take us inside this world.

] And it's a world of beatings, murders, bribes, and other kinds of plots. He was a member of the Elmwood Park crew. He was a big gambler. He was a big loan shark. And he worked for a guy named Marco D'Amico, who was their gambling boss and loan shark in that crew. Among other bosses in this powerful crew were Jackie Cerrone, who will go on and become the underboss and eventually the boss for a short

] period of time. and John no-nose DeFranzo, who will also go on to become the boss eventually. What was your relationship with Marco D'Amico? I talked about when I first came into the 18th district, when I came into work there, and they put me back in uniform, the first person I met was Rick Borelli. Rick Borelli, he was Marco's cousin.

] When I started gambling right away with Rick, within a couple of days, I'm being his face, and I'm calling and making bets. There was a restaurant across the street where every Wednesday and sometimes a couple days a week, I would meet with Ricky. And one of the first people he brought in there was Marco. Was Marco. And Marco would usually be with a person or two. And I thought they were just bookmakers.

] And I started being friendly with him, meeting him there. Then I started having card games Up in my apartment And, Because now I'm making, in the very beginning, I'm making first $100 extra a week. And within a couple of weeks, I'm making $500, $600 extra a week. And within about a month, I'm making $1,000, sometimes more than that. So now I'm having card games, relatively big card games, because I've got a bankroll. I've got probably about $5,000, $6,000, which seemed like a lot of money to me. Initially uh and after a while that was a daily that was a daily deal but uh so we we started having card games up there and then we started socializing we started now he'd be at these nightclubs all the time when when i'd go to make my payoffs he was part of the main group there he was one of the call he was right he was right under jack right under at that time originally Jackie Cerrone, and then he was right under Johnny DeFranco.

] But he was... And we became real good friends. We would double date and we spent a lot of time together. And we had these big card games. And that's when I realized how powerful these people were. Because after one of the card games, there was somebody that was brought in, a guy named Corrado. I'm pretty sure his name was I can't think of his first name, but Corrado was this person that somebody brought into the game. And after we finished playing cards, and I won all the time. I mean, I was a real good card player, and I wouldn't drink. I'd supply liquor and food and everything, but I wouldn't drink. And as the others drank, they were the same as at my office. After we finish up, this guy says, you want to play some? We can play maybe some gin. just human being. And he was there with another friend of his who just sat there and watched. So we played, not gin, but blackjack. We played and passed cards back and forth when you win. Then you're the dealer and back and forth. And I lost, I think I lost about $4,000 or $13,000 to him.

] I lost the cash that I had. I had cash about $5,000 or $6,000. And I gave him a check for the rest. You know, but everything I was doing was wrong, you know. Yeah, one of those nights. It's in there. And it's funny because you asked about Marco.

] And I thought, you know, oh, well, and whatever. And I gave him a check. I said, no, it's a good check. And it was. It was for my office. It was an office check that I gave him. And that next morning, I'm meeting with Ricky and with Marco at this restaurant across from the station before I go in and to work. And I said, son of a B. I said, you know, they had a bad night first ever. Marco wasn't at that game, at that particular game. And what happened? I said, I blew about 12,000. Okay, but you? Wow. And I said, yeah, I said, one of the guys at the game played some, I played some blackjack with somebody. What was his name? Eddie, Eddie Corrado. Eddie Corrado. He said, that mother, he said, stop payment on the check. He said, stop payment on the check. He said, because it wasn't nine o'clock. It was only like, you know, seven, you know, seven 30 or whatever. He said, and when he gets ahold of you, arrange to have him come to your house. Tell him you'll have the money for him at your house. So that's what I, that's what I do. So I stopped payment on it probably about five after nine. I get a call from, from Mr. Corrado. You mother fucker.

] I said, no, no. I said, there wasn't enough money in the account. I said, I'm sorry. I said, all right, then I'll be over. I said, no, no, no. I said, I'm in court right now. I said, I'm in court. I said, I'm going to be tied up all day. I'll meet you at my place. I'll meet you back there. Well, I'll be there. You better have that. I want cash and you better have it. Okay. Oh, I'm sorry. I'm sorry. I'm at home. Marco comes in. And he was there with Tony and Tony was there and Ricky was there. And Ricky was there. And they come over a little ahead of time and he comes in. I live on the 27th floor. The doorbell rings. Up he comes with some big mustache.

] I open the door. You better have the fucking money and whatever. And I try to look nervous. I try to look real nervous....

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Show notes

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 underworld, describing how corruption, bribery, and violence shaped the Chicago Outfit’s power in the 1970s and beyond. As a lawyer, gambler, and trusted insider, Cooley saw firsthand how mob influence tilted the scales of justice—often in open daylight. Inside the “Chicago Method” of Courtroom

Corruption

Cooley explains the notorious system of judicial bribery he once helped facilitate—what he calls the “Chicago Method.” He walks listeners through: How defense attorneys worked directly with Outfit associates to buy favorable rulings. The process of approaching and bribing judges. Why weak forensic standards of the era made witness discrediting the key mob strategy. His personal involvement in the infamous Harry Aleman murder case, where clear guilt was erased by corruption.

Life in the Outfit: Gambling, Debt, and Mob Justice

Cooley recounts his early days gambling with Chicago Outfit associates, including Marco D’Amico, Jackie Cerrone, and John DeFranzo. Notable stories include: The violent implications of unpaid gambling debts in mob circles. Tense interactions with bookmaker Hal Smith and the chaotic fallout of a bounced check involving mobster Eddie Corrado. How D’Amico often stepped in—sometimes with intimidation—to shield Cooley from harm. These stories reflect the daily volatility of life inside the Outfit, where money, fear, and loyalty intersect constantly.

Bob Cooley has a great book titled When Corruption Was King where he goes into even greater detail and has many more stories from his life inside the Chicago Mob.

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