November 1989. Bob’s undercover work has some serious consequences for an old friend. His days as an operative end suddenly when he flees Chicago.
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Pushkin previously on deep Cover.
Bob Cooley's mission had a name. The FBI called it Operation Gambat, short for Gambling Attorney. Bob's objective was to take down Pat Marcy and his corrupt political machine in the first ward, and Bob was making great progress. He had gotten Pat Marcy on tape. But would that be enough?
Every day that you continue to do this, it's a scarier day.
When should you stop.
To make matters more complicated? An investigative TV journalist had begun to expose what the FBI was up to. Pat Marcy and his guys now knew without a doubt the FBI was coming for them, which made Bob's work even more dangerous.
Now you're scared, and he's scared, and everybody's scared.
Anything could happen.
We were going to do everything in our power not to make a mistake, because this guy could get killed just like that.
You might recall it was Pat Marcy who asked Bob to help fix an infamous murder case back in the nineteen seventies. Bob had agreed to do Marcy's bidding, and he convinced an otherwise clean judge named Frank Wilson to take a bribe. As a result, a reputed hitman, Harry Elaman, walked free. Afterwards, the judge took a beating in the press. Rumors spread that he'd been bribed, and according to Bob, the judge told him angrily, you destroyed me. All of this old history was now suddenly relevant again. If the FEDS could prove that this case had in fact been fixed, and that Pat Marcy had orchestrated it, it'd be damning, and Bob hoped this might lead to a retrial of Harry Alamann for the murder of William Logan, which would be a big deal. It would give Bob a chance to write an old wrong. If fixing the Harry Alamann case was Bob's original sin, well here was a chance to make up for it. But how would the FEDS prove that this bribe had taken place? Sure, they had Bob's account, but in theory, what would really help was corroboration from the judge himself, Frank Wilson. He was now retired and living out in Arizona. According to Bob's handlers at the FBI, Steve and Marie, they wanted Bob to wear a wire and get the judge on tape. They say Bob was very reluctant.
Because he cared about Frank. He really did care about Frank Wilson. They were old, but because Frank was, in Bob's words, a good guy. He had been lured into the mafia's hornets nest by fixing a case of a mobster.
So Bob was trying.
To clean that up, I think a bit with Judge Wilson, but also get him to acknowledge that he had participated in a fix.
It killed him to have to do Frank Wilson. He did not want to do Frank Wilson. He really liked Frank Wilson.
Bob was in a real pickle. He wanted to help the Feds build their case, and in a way it was his case too, because Bob was deeply invested in making Operation Gambat a success. Yeah, Bob says he also wanted to give the judge a heads up about what was coming, that their backroom deal might soon be exposed. Bob, I believe there were things the judge could do to protect himself. As far as I could tell, Bob seems to have convinced himself with some magical thinking that he could both expose his friend and protect him at the same time.
There's no way I'm going to be the one cause of my friend the problem. I'm trying to help him. I'm trying to keep him from getting into trouble.
But Bob wasn't being fully transparent because Bob would be wearing a wire secretly recording their conversation, and as it turns out, this visit would set off a chain of events that would have profound consequences for both men. At this point, Operation Gambat would be coming to a close soon. Anyway, Bob knew it, and so did his handlers at the FBI and so on. Top of everything else, Bob also had to start planning his exit because the man known as Bob Cooley would not exist for much longer. I'm Jake Halburn and this is Deep Cover Mobland, Episode nine. The Vanishing Bob didn't go out to Arizona alone. He invited his old secretariat lover, Katherine Fleming. He hoped her presence might lighten the mood. So Bob settles in at a resort and arranges to have dinner with the Wilsons. Before dinner, Bob wires up. Then he and Catherine go down to the restaurant to find the judge and his wife.
We met, Hi, Frank, how are you? You know what's going on? And you know, hey, how you been just small talking? And we walked into the restaurant. We get our table.
They have an uneventful dinner together. Afterwards, they take a little stroll out to the parking lot, and we know exactly what's said next because we actually got a hold of the transcript from Bob's secret recording. The conversation among the couples seems friendly. They chat about the weather, what type of suntown lotion is best, and if Bob should visit the Grand Canyon. The judge tells Catherine politely, good seeing you again. Then Bob manages to pull the judge aside for a private conversation, and ever so casually, he brings up the Harry Alamann trial. He insinuates that the authorities are looking into it, re examining it. Bob says, quote, there's probably about half a dozen people that know the whole story on that, and the trouble is a couple of them are going to cooperate. Bob is bullshitting here, making up a story about some other guys who are supposedly cooperating. In other words, he's not telling the judge I myself went to the FEDS. I'm the source of all this. Bob goes on to say, quote, if I ever get called in to testify, I'm going to testify. The only way I can get in trouble is by perjuring myself. He then adds, don't worry about me, but don't put yourself in a bad spot by perjuring or something. It's not worth it, and this is his warning to the judge. Bob also reminds him that the statute of limitations is expired on any bribery charges, meaning the judge would in theory be safe to tell the truth. Bob then asks the judge, quote, what are you going to do? The judge replies, don't worry about me. As Bob rambles on, the judge keeps saying I don't know anything about anything. He says this four times. It's almost like he knows he's being recorded. At one point, Bob tells him bluntly, I don't want you to get mad at me, but you know, if it comes right down to it. I'm not going to take the fall. Finally, Bob and the judge walk back to where the ladies are standing. The judge's wife says, well, thank you very much. It was just a delight. Bob banters a bit more. He even says, if I come back, we'll do dinner together. We'll try the same place next time. As far as the FBI was concerned, this was hardly a home run. The judge did not admit taking a bribe. For his part, Bob felt that he had warned his old friend about what was coming. Though I suppose this was like warning your friend that you just set fire to his house. But maybe the fire was inevitable. For years, Chicago had been a dark hole of corruption. So many cases had been fixed, so many people were complicit, so many lies had been told. All of it just stacked up like deadwood in the shadows. And so if one guy was going to light a match to shed some light on the whole thing, you can be damn sure there was going to be a fire. Several months later, in November of that year, an FBI agent visited Judge Wilson's house and informed him that Bob Cooley was now a government informant, and that he had secretly taped their conversation. The FBI agent also told the judge that the FEDS were currently investigating allegations that he, Judge Wilson, had accepted a bribe. Wilson was then subpoenaed to appear before a grand jury in Chicago in early December over that Thanksgiving Judge Wilson's daughter, Mary Anne Duncan, remembers getting a call from her father.
He said, things are wanted to get really bad. He said, they want me to come in and do a trial. He said, if I come in and do a trial, I'll probably have a stroke. And I got off the phone and I had this terrible sense of foreboding. You know that feeling you have one You're stomach sort sinks. I just knew something really bad was going to happen.
Back in Chicago, Marie Dyson and her colleagues at the FBI were getting increasingly nervous.
We were constantly assessing what we had on our cases. Did we have enough? Did we need to get another conversation?
Did we with this?
I think he was getting to a point with everybody thought, Okay, let's start wrapping it.
Up, folks. Let's Enough's enough.
We don't need to have overkilled, and we don't need to get Bob killed.
Bob was getting ready to pack his bags. It was time, but first he had to talk with his family, say goodbye to his mother and his siblings who still lived in town. Bob invited them all out to dinner at a fish restaurant in a way for the coolies, this would be the last supper. As the family members gathered, Bob pulled each of his brothers aside and let them in on what he'd been up to. That for the last three years he'd been working with the Feds, and that now he had to leave town. Bob promised his brothers that at some point over dinner he'd find a way to explain all of this to their mother, tell her that he was leaving and why. But he never did. Why didn't you like tell them the truth at that point?
Like, I know, I just didn't say anything, and I would assume that you know, the family knowing me when they did and whatever would know that you know and would find out I did a fantastic thing.
In other words, his mom and his entire family would find out the truth soon enough in the papers and in the courts, and then his mom would know what he'd done, how he'd taken great risks and essentially giving up his life in order to clean up the system. Years before, when Bob's father was gravely ill, his had beseeched him to straighten out his life, to do something worthwhile. Bob hoped to prove that he had done just that this would be his redemption story. Bob, the wayward son, the one who always caused so much trouble as a kid, breaking windows and cheating on tests, had finally made good and people would know it, or so Bob hoped so. As dinner ended that night, Bob's mother still had no idea that her son was leaving town. Bob says his brothers were angry at him for not telling his mother and not preparing her for what was to come, and perhaps they understood better than he did just how bad things were about to get. Bob coolly vanished on November twenty ninth, nineteen eighty nine, the Wednesday after Thanksgiving, when when the big moment came, he felt strangely unprepared.
I had two suitcases with me. These are my belongings and I'm going to be leaving, but I have no idea where I'm going. I have no idea what I'm going to do next.
Now at this point he might be thinking, what there must have been a plan. This was the FBI we're talking about. They don't just put informants on a plane and wish them good luck. I mean, wasn't Bob and the Witness Protection Program or something well that would be the path for your typical informant, But as you know by now, nothing about Bob's typical. Long before his departure, the FBI insisted that he meet with a representative from the Witness Protection Program. A guy actually came to Bob's apartment and gave a whole spiel about what his new life would be like.
At some point I said, look, I'm not interested in your program. And he said to me, you don't have any choice, and and I said to myself, this is Bob Cooley you're talking to. I don't have any choice. And that was the end of that.
This didn't really make sense to me, And to ask Bob why he rejected this guy and the protection he was.
Offering, because then I would be classified in a lot of people's minds as a rat or a snake, because these are the people that go into witness protection because they're in fear of their own safety, and they're doing it to save their own skin.
You're telling me you turned down witness protection program just because you didn't want it, you didn't like the branding that went with it, that you'd be a rat.
Well, that was initially my reason, But as I thought about it, there's no way I'm going to be living like I'm in prison of some sorts. I'm in a motel with some strangers. I know how I am. I'm going to do what I damn well please, that's me.
Bob also says that he didn't think the program would actually protect him. He worried that Pat Marcy, who apparently had eyes everywhere, would pay someone off or somehow figure out where they'd stashed Bob. So when it came time to flee Chicago, Bob realizes, shit, he has no real plan, But the Feds were a little more prepared. An hour before his departure, they handed him a plane ticket to Fort Myers, Florida.
All they said was when you land, find yourself a hotel and then give us a call and tell us where you are.
So there he was on a plane headed down to Florida, winging it. He didn't even have a gun because he knew we couldn't take one on the plane, and from the moment he lands in Fort Myers he feels exposed.
I get off the plane, I look over and nurse a sign Marco Island to the right.
Marco Island was a favorite destination for so many of the mobsters that he knew back in Chicago. In Bob's mind, it was pretty much Gangster Island. A few of these guys even own property on the island, and now here was Bob essentially on their turf. He couldn't believe it. He probably should have thought about this the moment he saw the plane tickets to Fort Myers, but everything had happened so quickly, and now well, here he was. So Bob checks into a local motel, calls a number that the FBI has given him. Sometime later, an agent shows up offers to take Bob out to dinner. They go to a nearby restaurant, but first the agent does something that unsettles Bob.
He walks over, opens the trunk, takes off his gun, puts his gun on the trunk. What are you doing? He says, I never wear my gun when I'm drinking. Here's my protection.
Later that night, Bob's back at his motel.
I'm in this room by myself with no weapon though nothing you know, along with everything else. Yeah, how did I sleep? I didn't sleep real well that night. I probably slept maybe half an hour if that.
Just A day or so later, Bob was on the run again, heading west to his next hiding spot. Meanwhile, back in Chicago, the ship was about to hit the fan. Carol Marine, the journalist, was still looking into the first ward.
I'm sitting in my desk at NBC in the newsroom, and a source I hadn't talked to it in about five years, said Carol.
Get a picture of Bob Cooley.
He is going to break the first ward.
Carol began to connect the dots, and as she did, she got a sense of the scope of operation Gambat.
So this is like a not just a cascade, It's an earthquake on Chicago politics. I mean, this is a staggering revelation involving a lawyer. Virtually no one outside of a circle of real insiders knew at all.
Carol scrambled to find as much as she could, and she broke the story on the evening news.
The Cattle High Teams of.
Ten Tonight exclusive details of a huge federal investigation into the heart of organized.
Crime in Chicago.
For years, Chicago's First Ward has been openly referred to as the Mobs Ward. Tonight, Carol has the exclusive story of the man who apparently infiltrated the ward's politics and its bosses.
Ron For approximately five years, a Chicago lawyer has been a government informant, secretly recording conversations with some of this city's movers and shakers, some of whom have long been reputed to have organized crime connections. The identity of this informant will come as a shock to some powerful people. The man who wore the wire and infiltrated Chicago's First Ward is forty seven year old Robert J. Cooley, a former policeman the son of a policeman, Cooley became a politically well connected Chicago attorney five years ago began to go undercover for the government, taping conversations with Chicago Alderman, State senators and judges.
And that was it. Bob was outed the news made a seismic impact. One FBI agent went to City Hall and witnessed an unforgettable scene involving Johnny Diarco Junior. Johnny was the poet and state senator whom Bob had bribed on tape. Johnny Junior was standing in a phone booth when apparently he got the news. The FBI agent would later recount the scene in court, saying Johnny Junior quote gasped like he was in pain, almost as if the wind had been knocked out of him. He then fell to the floor, holding his head in his hands, and called out, oh my God, almost right away. A number of newspaper articles were written about Bob. One of them began, quote, most people know Robert Cooley as a fast talking lawyer, an inveterate gambler who bragged of his political prowess and said he could fix almost any case. It described Bob as a lawyer who quote rarely opened a law book and instead relied on his friends to answer the most basic questions of law. It quoted a friend of Bob's who said his reputation was never that of a scholar, but he let it be known that he could occasionally use his contacts to move mountains. The article ended by noting that Bob, the self proclaimed mover of mountains, liked to gamble and quote, built up debts to organize crime, and feared for his life. Other journalists wrote articles in a similar vein, and soon Bob's life was being condensed into a few simple facts and assumptions. He was a corrupt lawyer and a braggart, a man unversed in the law, an opportunist who flipped to protect himself.
And I'm a basket case when I see this, and I'm envisioning my mother sitting. My mother's in a convalescent home over there, a carmel aid home, and I'm envisioning her watching this and with all her friends, you know, all their friends are seeing all this, making me out to be the rat of all time.
And the facts being reported weren't entirely wrong. Before he flipped, Bob did owe money to some bookies, but remember he was mostly off the hook for those debts, and at the time, as far as I can tell, Bob was in no immediate danger. In any case, Bob was absolutely pummeled in the press. He had hoped, perhaps naively, that he would emerge as a hero in the papers, that his dirty past and other shortcomings would be eclipsed by the good he'd done, that his mother would finally see him as righteous. Instead, he came across in print as the rat of all time. Bob wasn't the only one navigating this mess. His brother, Joe Cooley, was a police officer at the time. He told me he had a falling out with some of his fellow officers when they called Bob a snitch. Joe says he didn't care. He was proud of what his brother did. Bob's other brother, Dennis, the former prosecutor, says he also got an ear full.
For one thing. Now, I went from mister straight, narrow, mister nice guy, to mister your brother's a fucking snitch.
Dennis says his bigger concern was now that Bob had vanished, that the mob might ex act retribution on him and his family.
I was afraid for my safety, and I was afraid for my wife's safety, and I was afraid for other relatives out there. You know, you didn't know, You didn't know how they were going to react. You didn't know if someone was going to come looking for you.
Yeah, I was.
I was concerned. Sure, I have been a full na to me.
Bob says that before he ever left Chicago, he told the FBI how important it was to him that no harm come to his family. Apparently, the FED seemed confident that the Coolies would be okay, as one prosecutor told me rather surprisingly, they'd never seen a situation in Chicago where the mob had taken retribution against family members. But the FEDS could make no such promises for Bob. After all, Bob would be the prosecution's star witness and the trials against the mob, which meant for the foreseeable future, Bob he had a big, fat target on his back and would be on the run for quite some time. Before we get back to the story, I want to mention in this last segment we talk about a suicide. Just a heads up, Bob's role in Operation Gambat was far from over. After all, courts moved slowly. It would take years to prosecute Pat Marcy and other first Word targets, but the process was underway. Prosecutors began issuing subpoenas. They would end up charging at least two dozen men, politicians, lawyers, judges, and cops. In fact, just a week after Bob vanished, on December sixth, nineteen eighty nine, the wheels of justice were already turning. A grand jury was convened in Chicago. It was looking into, among other things, whether Judge Frank Wilson had been bribed in that infamous murder case. He had been subpoened on that day. However, Wilson failed to show up in court. If you recall, the judge's daughter, mary Anne, had been worried about her father when he had called her a few months back told her that things are going to get really bad. Then in February, Marianne got a call from her mother telling her, your father has died.
And so I said how, I said, he was okay. He had some problems with his carate artery, but I said, yeah, he's all right, And she said yeah.
Well, as in yeah, well these things happened. He was seventy four years old and hardly in perfect health, so it wasn't totally surprising that he passed away, at least not initially. But when she got out to Arizona, it was a different story. When Marianne arrived at her parents' house, she got to talking with a neighbor and he filled her in on what really happened.
He said, well, your father took his own life. And I said, oh, no he didn't, and he said, yeah, he did. He goes I was out now I saw him afterwards.
Days before, the neighborhood heard a gunshot near Judge Wilson's house. He came over and found him. He had shot himself. Mary Anne says her mother was in denial about what had happened. That she kept on insisting that her father didn't mean to do it, that it was an accident.
And then.
The second night I was out there at two o'clock in the morning, I see her and she's in the garage where he had done it, and she is on the floor trying to clean up the blood with a toothbrush, and I said what do you do and she said, well, I just want to clean it up so no one sees it.
Judge Wilson left two notes, one for Marianne and one for her mother. She told me that the two notes couldn't have been more different.
My note was helping me do all these things, to take care of all these matters. Hers was basically, I'm really sorry. I just kind of like, I can't take it anymore. I don't want you to lose a pension. Basically, that was kind of it. I think he said I love you or something, which she said to me too, which she didn't say often.
Marianne did the things that she had to do to care for her mother and to tell the members of her extended family.
He was always like the rock of the family. If anyone had a problem, they would go to him. So it's like, you don't expect someone like that and to commit suicide.
After her father's death, mary Anne was in an incredibly difficult situation for so many reasons. She was devastated and grieving and depressed. There were all the things that she had to do for her family, and on top of that, eventually the judge's death made the news, along with allegations of corruption, which made it all the harder.
I just wish he had not done that and he had fought, you know, because that's like another thing when someone does that, that makes him look really guilty.
And in a way she was left to answer for him, which was an impossible task.
I feel like if there's two sides of the story, people can make up their mind. I mean, I just feel like he never got his side of the story to this.
Mary Anne strongly believes that her father is innocent, that he never took the bribe, and I should reiterate aside from the allegations in this one case, he appears to have been an honest judge. Mary Anne sent me a newspaper article from the nineteen sixties. The article praised her father's integrity. It even began with the words Frank J. Wilson is a man to be admired. It's hard telling a story like this because the judge can't defend himself, can't push back against Bob's narrative, can't offer a new evidence or extenuating circumstances. There's just a notorious trial, a death, two suicide notes, and a daughter who's doing her very best to make sense of it all.
My dad's dad and pas. I don't know where he is, but it just doesn't seem fair.
Bob doesn't remember exactly when he heard the news about Judge Wilson's death, but it was probably a few days after the fact.
And I got a call. I don't remember who called me. Somebody called me. I mean, I broke down I broke down. I just I cried for hours because I felt maybe it's because of me. I felt that way. Maybe it is, and I'm hoping and praying to myself it's because of his own other problems. But no, that was a that was a real rough rough go for me. That was a rough go. Cam It's springing back, springing back, springing back some bad memories.
Bob says, after hearing about the judges suicide, he got in his car and just started driving. He was staying in Colorado at the time, and he headed into the mountains.
I don't know if I was going to drive off the cliff for what I was probably doing about Who knows how fast. I was going as fast as I could. Yeah, and I got pulled over by This is silly I got. I got pulled over by a trooper and he was really angry. When he came up to the carpet. He probably saw me looking like I look right now and as you told him about to your friend of mine just committed suicide. I have no idea why he obviously believed me, because he tried to see he tried to consult me, and he just sat there with me, probably for maybe half an hour and convincing me to go back home.
When he was done telling me this story, we took a break. I had never seen Bob so broken up. It was like he just bottled all of this up. After he had a moment, we started back up again. Have you ever talked to anyone about this about like?
No, I would to me, it's something I have to handle myself. And it took a while to you know, to get over it. But you know, but then it's like, you know, like I would tell people, that's the last week's news. You know, that's the mindset you have to have. I mean, things I have to live with.
And I kind of got it. There was no looking back for Bob, no dwelling on what had happened, the death of his friend, all the bad press that he'd gotten, the life he'd once had in Chicago, the very man that he'd once been. All of it was last week's news. What mattered now was finishing what he'd begun. What mattered was staying alive to testify in the trials against Pat Marcy and the other targets. What mattered was fixing his original sin and ensuring that Harry Alamann was retried. There was still a chance that some good might come from this, something to justify all that had been lost For Bob, that's all that mattered. Now. Next time on deep Cover, our final episode.
They have nothing but this memory of how they last seen their family member, laying on a street full of bullet holes, moaning.
I thought that it's very wrong for judges to get paid off so that hitman can continue to murder people. Nobody wants to testify because their mothers scream at them that you're going to get murdered.
And they said, you can't go back home, and I supplied. They said, supposedly somebody was on the way out there to kill me.
They're surrounded by agents, they're in bulletproof vests, they've got automatic weapons everywhere. Yes, you are the center of the universe.
Deep Cover is produced by Jacob Smith and Amy Gaines and edited by Karen Chakerji. Our senior editor is Jenuera. Original music in our theme was composed by Luis Garra and Vaughan Williams as our engineer. Our art this season was drawn by Cheryl Cook and designed by Sean Karney. Nea Lobell as our executive producer. Special thanks to Heather Fame, John Schnarz, Carl mcgliori, Maya Kning, Christina Sullivan, Eric Sandler, Mary Beth Smith, Brant Haynes, Maggie Taylor, Nicolmarano, Magan Larson, Royston Bserve, Lucy Sullivan, Edith Russlow, Riley Sullivant, Jason Gambrell, Martin Gonzalez, and Jacob Weisberg. I'm Jake Halpern. Suicide is a difficult topic. It can be hard for people to talk about suicide or get help if they're in danger, but there are resources available. The National Suicide Prevention Hotline is an excellent resource. It's free, confidential, and available twenty four hours a day. The number in the US is one eight hundred two seven three eight two five five. That's one eight hundred two seven three talk