Pushkin previously on Deep Cover.
Bob Cooley fled Chicago in November of nineteen eighty nine. Bob's life as he knew it was over. He had rejected the witness protection program and instead opted to improvise. He took on a new identity and planned to hide out Meanwhile, back in Chicago, Bob's efforts resulted in charges against at least two dozen men, lawyers, judges, cops, and politicians. Chief among them was Pat Marcy, who effectively ran the first ward, the Mob's political stronghold.
So this is like a not just a cascade, it's an earthquake on Chicago politics. This is a staggering revelation involving a lawyer. Virtually no one outside of a circle of real insiders knew at all.
Bob's days as a covert operative may have been over, but he still had work to do. He would be the prosecution's star witness in a series of trials. This was the final stage of Operation Gambad, the goal break the chokehold the Mob had on Chicago. There's a little story Bob told me that kind of sums up what his life was like after he fled Chicago and It's about of all things furniture.
I started off I first, when I first left town. I started off with all my own furniture and all the rest of it.
And all the rest of it, you know, like a toaster and a can opener and a TV. Not just that. Initially, Bob built a little nest for himself. After bouncing around from east to west, he settled down in Richmond, Virginia and started getting all domestic.
I had met a girl who had moved in with me. She thought maybe we'd get married, but that wasn't my idea. But she had just moved in with me about a week before, and I went to Chicago for a trial.
That was the rhythm of Bob's life. Now, hide out, keep a low profile, and then every so often, hop on a plane back to the Chicago area, show up in court, take the witness stand, and then poof vanish again. All told, Bob would end up testifying in nine trials. Anyway, After one of his court appearances, Bob is ready to head home back to Richmond, where his girlfriend is waiting for him. But first Bob needs to stop by an FBI office just to check in.
They had six agents standing there with machine guns and with vests on, and they told me to put a vest on. And they said, you can't go back home. And I said why. They said, supposedly somebody was on the way out there to kill me.
Bob tries to digest all of this. I mean, things were going pretty well for him back in Richmond, but apparently it was time to move again.
I said, well, I've got some stuff i'd like to get, you know, back home, at my house. And so the next day I flew into Richmond. A couple of agents met me there. We went to the house and my girlfriend I forgot her name now, wasn't home. She was at work, and I just packed up a bunch of stuff and left her a note. You know, I got to leave. Something came up. I'm not coming back. You know, everything here is yours.
And that was that the end of one of Bob Cooley's many lives. So he started over in North Carolina, where he stayed until there was another scare and he had to flee again. It had been twenty years since Bob first got involved with the Mob. Ever since then, he had been haunted by his relationship with its political czar, Pat Marcy and one of its hit men, Harry Elmann.
Now they would both be prosecuted. This was the reckoning, the moment when Bob would have to stare them down in court, tell the world what they'd done, and explain his own role in it all. This would happen in two separate trials that took place in the nineteen nineties. These trials would in many ways to find the success or failure of Bob's mission, and through it all, Bob's main challenge was to stay alive so he could finish what he started. I'm Jay Colburn and this is Deep
Cover mob Land, our final episode the witness. Before Pat Marcy was indicted, prosecutors invited him to their off for a little visit. Tom Durkin was there for that meeting. Today he's a federal judge, but at the time he was an assistant US attorney.
Pat Marcy came in with his lawyer. The attorney explained what the charges would be.
Marcy was older now, he was in his seventies and not in the best of health, and he was in hot water. Marcy was about to be charged on multiple counts, including racketeering, bribery, and extortion. The prosecutors wanted to see if Marcy might cooperate.
And I distinctly remember Pat Marcy saying good luck to you and standing up and walking out.
In other words, go to hell. So Tom and the other prosecutors had to build their case, and they had a lot to work with. For starters, they had all those secret recordings that Bob had made, which they could play for the jury. These would prove that Marcy had orchestrated bribes. Sure, sometimes Marcy spoke in code, but that's where Bob would come into play. He could get on the witness stand and offer context, almost like a translator,
decoding mob speak. The prosecutors also wanted to prove that Marcy had arranged to fix court cases in the more distant past before Bob had flipped, like that notorious murder case back in the seventies involving the reputed hitman Harry Elaman. The Feds wanted to prove that Marcy had schemed to fix that case, that he was the one who'd recruited Bob Cooley to bribe the judge. But proving this would be much harder. Sure, Bob could testify, but there were
no secret recordings to back him up. So who could corroborate Bob's story. The judge on the case, Frank Wilson, was now dead. He had taken his own life, and that left only one person, Catherine Fleming. If you recall in nineteen seventy seven, the year of the Harry Elamann trial, she was Bob's secretary and lover, but she knew little about his shady dealings.
I wasn't looking to figure it out because it was none of my business.
But Catherine was with Bob at the restaurant when he made the payoff to Judge Wilson. She didn't see the actual payoff or even know about it at the time, but afterwards the judge had told her, you look like a nice girl, stay away from him. Tom Durkin, the prosecutor, felt that if he could persuade Catherine to testify, she could be the lynchpin. Everything she witnessed indicated that Bob was telling the truth. Catherine agreed to cooperate, but her family was unhappy, especially her mom.
Oh, she went nuts. She had a fit, lots of screaming. She demanded that I'd not testify, that it had nothing to do with me, that Bob was wrong to do this, wrong, to involve me. She felt that he was a horrible person. She felt that everyone was you me, and the mafia would kill me.
Even so, Catherine felt she had to do something.
I thought that it's very wrong for judges to get paid off so that hitman can continue to murder people, and nobody wants to testify because their mothers scream at them that you're going to get murdered. And I wanted to do the right thing.
Catherine's testimony would be a huge boost for Tom Dirkin and the prosecution, especially because she had no reason to lie. She was just a regular civilian, a bystander caught up in a tangled scheme of corruption, and by testifying she would in effect be taking on the mob. In short, she bolstered Bob's credibility big time.
It was remarkable corroboration from a witness who had no motive to lie. I thought that was the best piece of corroboration I've ever had in any case I ever prosecuted.
So that was that the prosecution's case was coming together. They had Bob, they had his secret recordings, and they had Catherine Fleming, the stalwart secretary who would not be intimidated. The trial of Pat Marcy kicked off on December fourteenth, nineteen ninety two, almost exactly three years after Bob Cooley fled Chicago, and on trial alongside him as co defendant, was one of Marcy's associates, the first word Alderman Fred Roady.
In his opening statement, Marcy's defense lawyer Ed Jensen told the jury quote, Robert Cooley is a liar who will say or do anything to convict Pat Marcy. He's an envious man who has spent his whole life lying and cheating, and he has decided to put these talents to work for the government. So that was the game plan. Smear Bob before he even took the stand. Make Bob Cooley
look like the rat of all time. Eventually, Bob arrived at the courthouse to testify, and for the first time in year, he came face to face with Pat Marcy.
I was brought into the courtroom. I was put up in the chair. I'm sitting up there in the witness chair. I see Pat over there and he's glaring at.
Me, Bob says. Marcy's lawyer approached him. The two men knew each other brushing shoulders in the city's courts.
Jensen comes walking up to me while the jury is being brought in and he says, how are you doing, Bob? You know you look good? Everything okay, I get the fuck out of here.
Bob was a witness for the prosecution, so they got him first for the direct questioning. Tom Dirkin, the prosecutor, asked Bob to tell his story, the whole saga of how he got mixed up with the mob in the first place, how he met Pat Marcy, and what Marcy asked him to do. Bob was calm and collected, clarifying the smallest of details. As a former criminal defense lawyer, Bob knew exactactly what he needed to do. Tom says Bob's performance as a witness was one of the best he ever saw.
Every question I had was answered directly by him. The evidence we were able to play the tapes. We put up pictures of the main players as he was talking about people.
All the while Pat Marcy sat there as if none of this had anything to do with him.
You couldn't get any emotion out of him. He wasn't grimacing or rolling his eyes or muttering under his breath or anything like that. He's very stony faced.
Bob says he also remembers Marcy's cold, hard gaze.
Pat Marcy is staring at me. When he's staring at me, I give him a wink. I give him a wink and a smile, and he starts coughing. He started coughing and wheezing, almost uncontrollably.
As all this is happening. Tom has his back to Marcy, so we can't see him, but he remembers hearing coughing in the moment. Tom didn't think much of it, but turns out it was an omen of what was to come. A day or so later, Marcy's lawyers announced that he'd had a heart attack.
Tonight, Pat Marcy is in critical condition in the cardiac care unit of West Suburban Hospital in oak Park. Despite defense objections that the seventy nine year old Marcy should not be tried at all due to poor health.
The plan was to prosecute Marcy again when his health improved, but it never did. The case against Marcy ended in a mistrial. A short while later, Marcy died. Now you might think that Bob would be devastated by this. I mean he risked his own life and spent the last three years on the run, all in the hopes of nailing this guy and sending him to prison. And now this, but that's not the way that Bob saw it. Bob,
in classic Bob fashion, credit for Marcy's death. Wait, are you saying that you think you caused him the heart attack?
I have no doubt in my mind. I have no doubt in my mind. But I was gonna say, because this man had so much hatred towards me in this system.
The truth is, there's no real proof that Marcy had a heart attack right there in the courtroom while Bob was winking at him. But as Bob tells it in his mythology, that's how it all played out. In other words, he won, though arguably Marcy lived by his own rules to the right bold age of seventy nine and checked out just in time. I asked Tom, the prosecutor, if he felt that Marcy had basically escaped justice.
He didn't escape justice. He was indicted. He was held up to the public as a person who had fixed murder cases. He was on trial in a courtroom in front of a jury. A lot of the secrets of his life were exposed. So he didn't escape justice. Did he escape going to jail, sure, but at what price he died?
Pat Marcy's death was a mortal blow to the First Ward. Marcy was more than just the boss in so many ways. He was the first Ward. He'd been there for decades, and his connections, his know how, and the fear that he conjured it all died with him. No one could really fill his shoes, and the other possible candidates, well, they went down with him. Fred Roady was convicted on multiple counts of racketeering and extortion. He was sentenced to
four years in prison. As for John Diarco Junior, the poet and state senator, his case also went to trial. He was convicted of extortion and sentenced to three years in prison. In the years since Marcie's death, the political boundaries of Chicago's war Words have been redrawn and then redrawn again, and the old First Ward, in both shape
and power, is no more. Bob may rightly claim credit for the downfall of the First Ward, but his most defining moment would come in another trial where he would face off with the hit man Harry Alaman and try to atone for his own original sin. More on that after the break, after the trial of Pat Marcy and Fred Roady, much of Bob's story became public, and one of the biggest revelations was this Bob had bribed a judge and helped Harry Alamann, the hit man, go freely.
That but Catherine Fleming, Bob's secretary, had provided some corroboration, And this, among other things, raised the question would prosecutors go after Harry again some twenty years later. Mind you, doing this wouldn't be easy. Harry had a very powerful ally on his side. And I don't mean the mob. I'm talking about the Fifth Amendment of the US Constitution. It said that no one could be placed in double jeopardy, meaning you can't be prosecuted for the same crime twice.
But turns out state prosecutors came up with a clever workaround. They argued that because the original trial appeared to have been fixed, well, then Harry had never really been in jeopardy in the first place. Hattie. This question was actually appealed all the way up to the US Supreme Court. In the end, the decision was Harry could be retried.
Now.
To give you a quick refresher. The first trial of Harry Alamann occurred back in nineteen seventy six. There were two eyewitnesses, both of whom identified Harry as the killer. The public and Chicago media were shocked by the not guilty verdict, but no one was more deeply impacted than the family of the victim, Billy Logan. Billy's niece, Johanna Santanello says her relatives were haunted for years by what had happened.
They have nothing but this memory of how they last seen their family member laying on a street full of bull of the hole's moaning.
They wondered how exactly that trial had ended in an acquittal, and they held on to the hope that somehow justice still might be served. And then finally, in nineteen ninety seven, two decades later, Harry was put back on trial, thanks in part to Bob Cooley and the fact that he would testify. But the whole thing left Johannah feeling worried.
Because I just felt, what if he walks again, you know, how would my family handle that or could they handle any more of this?
In many ways, this retrial was a culmination, a moment of truth not just for the Logan family or even for Operation Gambat, but for everyone in Chicago who'd witnessed untold decades of judicial corruption. The credibility of the judicial system itself seemed to be on the line, because in the end, laws and judges and courthouses don't mean a
damn thing if no one has faith in them. As the trial got underway, the prosecution called its witnesses to the stand, many of the same people who testified twenty years earlier. It was a bit like the reunion of an old TV show, with the same actors and a few new twists. There was the neighbor who said he'd witnessed the murder, the accomplice who said he'd helped Harry plan the whole thing. And there were new witnesses too, including Bob Cooley. Bob says he showed up with his own security detail.
Well, I guess it was like the mayor or the rising coming in. They were so worried about my security because of obviously this was going to be a case that would be making history.
It's a very big deal.
Investigative reporter Carol Marine covered the trial. She also remembers all the fanfare surrounding Bob.
They're surrounded by agents. They're in bulletproof vests. They're guarding you.
They've got automatic weapons everywhere.
Yes, you are the center of the universe.
When he finally took the stand, Bob told the courtroom how in the past he'd been a fixer for Pat Marcy and the first ward he was in effect a tool of the outfit who'd been asked to protect when of their most valuable assets, Harry the hook Alaman. Bob explained how in the original trial he'd bribed the judge, Frank Wilson, and how later after the not guilty verdict came out, the judge had told him, you destroyed me. Carol was there in the courtroom for this moment.
You know, Bob Cooley does not demonstrate much emotion at all. He's got a pretty flat affect. But there was a point in his testimony talking about really almost forcing Frank Wilson to take the money in a men's bathroom. I mean, he choked with emotion and had to kind of swallow hard and.
Keep talking.
Because he knew that he was one of the instruments of Frank Wilson's demise. He couldn't have been other. Yes, the outfit ruined Frank Wilson. Yes, Frank Wilson ruined Frank Wilson, But ultimately all of the players in the surround sound of that were responsible for the death of Frank Wilson.
Afterwards, Harry's lawyer had a chance to cross examine Bob. His strategy from the start was to discredit him, to dredge up Bob's checkered past. He asked Bob if during his days as a cop he'd ever been paid off. Yes, said Bob, He'd taken so called street money that typically meant tips or payoffs from businesses, you know, like bars that want to cozy up with the cops. The defense lawyer kept hammering away at Bob, portraying him as a
shifty and shadowy character. In response, Bob was remarkably candid. He didn't make elaborate arguments or justifications. He just kind of took it on the chin. At one point, he said, quote, I'm not making any excuses for what I did. I did what I did, but it was an easy way to get to the top during that time, and I took the easy route.
This guy is trying to make me out to be somebody who's you know, who's a crooked cough passing out bribes.
Because I guess what he's trying to do is the classic I'm going to turnish your reputation and credibility. But the whole purpose of you appearing today as as a guy who fixes cases in places bribes.
It's given me credibility in that sense.
The whole process was tricky for Bob. He wanted to be seen as the guy who'd cleaned up Chicago, but in order to do that, he had to admit publicly to all the most questionable and unsavory things that he'd ever done. The danger was that these admissions would define who Bob really was because everyone was trying to make up their minds about Bob. In his closing statement, the prosecutor told the jury quote, I'm telling you you have to like Bob Cooley. You don't have to like him,
but you know what. Bob Cooley faced what he was. As the jury finished its deliberations, onlookers packed into the gallery to hear the verdict. Johanna Santanello was there with the other members of a Logan family, hoping that maybe finally there'd be justice for Billy. The jurors came into the courtroom and then the verdict was announced for the.
Murder of William Logan guilty, and it was like, oh my god, it's happening. All these years they waited my aunt and my uncle and my mom to hear that guilty, and it was finally like a burden was lifted off of them. Of course, their brother could never be replaced, no matter, you know, but to see him actually have to pay for what he did meant the world to them.
So, according to the Chicago Tribune, when the verdict was announced, Harry Alamann didn't flinch. He simply blinked his eyes and stared straight ahead. Harry was eventually sentenced to one hundred to three hundred years in prison. He died behind bars after the trial. As reporters clamored for quotes and comments, one prosecutor proclaimed, quote, this will close the books on an ugly era in Cook County. It's a great day for American justice. The one person who was conspicuously absent
at that moment was Bob Cooley. After testifying, Bob flew off to another undisclosed destination, vanishing once again even so Bob's presence loomed large in the courtroom that day. After all, he was the man who'd both started and finished this saga, the fixer who bribed the judge in the first trial and then exposed his own trickery at the second trial. He was a rat or a hero, depending on who you asked. But one thing was clear. Bob's work in
Chicago is now done. He hadn't expected to survive this process, but he had. In fact, he was just fifty five years old. So now what what kind of life could he really expect? And had it all been worth it?
Caam driving down a desert highway here? And so you got to make him turn left, turn.
In a mile. Well is.
Dusty and bleak out here. After almost a year of talking to Bob on the phone, I went to see him in the obscure little corner of the world where he now lives.
You got to make a left up here. Oh, oh, yeah, somewhere. I think I'm about to miss out here. It is here, It is okay, Wow, it's.
Easy to miss.
Bob lives in a modest house at the edge of the desert.
Here.
He has a small bedroom which he calls his cubby hole. His bedroom floor is stacked with cylinders of pringles and jugs of V eight vegetable juice that Bob buys in bulk to save money. The place looks like what it is, a hideout.
Hi are you Rosie?
Bob has a roommate, a woman named Rosie. When I visited, she was wearing a house dress with brightly colored, psychedelic looking flowers. She's actually the one who owns this house. Bob told me that he's lived with her on and off for roughly a decade.
She said, I'm pretty much of a recluse. She said, I keep to myself or whatever. And I said, you know, well, I think i'd like to move in. She had no idea who I was.
Rosie told me that she knew the broad strokes of Bob's life, but never asked about the details.
We don't talk.
Wait, how come you never talk your roommate.
He lives his life. I live my life minus with the dogs back there, and his is in here, so that's it. He comes in the kitchen. I'm not in the kitchen. He does all the cooking. I don't do any cooking.
But aren't you curious?
Like he used to work for the MOB as a lawyer.
Does that make you want to know more?
No?
No, no, I don't.
That's me.
No, I don't need to know.
So in some ways, Rosie is the perfect housemate for Bob. She doesn't pry, though I should point out they did, in fact talk. They argued more or less constantly during the time that I was there, not small things like whether the living room needed dusting or how the pillows were situated on the couch. Rosie told me that Bob had messed them up.
I'm kind of embarrassed, though I hope he doesn't take a picture of that.
Kidding, you're embarrassed, Give me a break.
You guys are a regular odd couple. I gotta tell.
You we are we if we would be married, I polly killed him by now.
Just to get the insurance right.
Absolutely.
Eventually, I suggested that Bob and I get out of the house get some space. So we hopped in my rental car, and as we drove we chatted. He told me how lonely he was in the years after he first left Chicago.
As I'm driving around, I'm so jealous of people. Look, I say, somebody with somebody in the car with them, and I'm jealous. I mean, it's really hard to explain this.
I'm curious, like, here you are, You're in this town, you're at this roommate live with you for eight years and knows nothing about you've got. You said, you've got no friends in this town. I mean, are you good with that?
Are you at peace with that?
Or are you at the moment at the moment, yes, you know no, As I said, what are you gonna? What am I gonna do? I can't feel sorry for myself. It's such a decision I made, and I suspected it would be bad, never as bad as I'd got in terms of, you know, fighting off the loneliness for a long period of time.
As we continued driving, Bob pointed out a few of the local landmarks, restaurants and the like that he told me he was so strapped for cash that he hadn't really dined out in years. Bob also showed me the office of his lawyer, who recently helped him file for bankruptcy. Bob told me that he'd been living off credit cards for a while, but then the monthly payments got so high that they ate up what little money he made from Social Security, so declaring bankruptcy, it had been kind
of a relief over the past twenty five years. It hasn't always been like this for Bob. He says that when he initially left Chicago, he had some money in savings, but Bob, ever the gambler, had made some risky bets on the stock market and lost almost all of it. Bob also co wrote a memoir with a journalist, Hillel Levin. He made some money off the book, but that was back in two thousand and four, and in the years since then, he's been kind of scraping by. It's ironic really.
As a kid, Bob loathed the feeling of being poor. Remember he hated that his mother had to comb the shelves looking for dented cans so she could ask for a discount. This, as much as anything, fueled his ambitions to become wealthy, to become no tie gold chain Bob a guy who walked around town with thousands of dollars in his pockets and now here he was all these years later, clipping coupons and buying V eight and pringles
in bulk to make his money. Last in the Hollywoo version, of this story, the Bob character would likely have ended up on the beach somewhere, maybe down in the Caymans, but that's obviously not how it panned out for him. And this got me thinking, what was the ending that Bob deserved, you know, given everything that he'd done. I mean, it was complicated. Bob was the guy who induced his friend into taking a bribe that ruined him, a guy who helped a murderer walk free, a guy who prevented
a female cop who'd been beaten from getting justice. But this was also the guy who tried to right these wrongs. He'd shown tremendous courage. Bob made a stand against the mob and expose systematic corruption, and the impact he had in the city of Chicago, it's indisputable. Here's Carol Marine, the investigative journalist.
Bob was one of the most consequential witnesses that ever took the stand in a federal organized crime trial or probably almost any trial. He did this city and this state a great service. He risked his life. He did something that no one else had done. He penetrated the first Ward and he took down its power brokers. It was tremendously important in fighting public corruption.
Of course, Chicago still has its challenges. In twenty nineteen, the city's longest serving aldermen, a guy named Ed Burke, was indicted on fourteen counts of racketeering, extortion, and bribery. Burke went down because another city alderman betrayed him. That guy wore a wire for two years and made a series of secret recordings. It was a long con. Seemed like he took a page right out of Bob Cooley's playbook.
Operation Gambat may now seem like ancient history, something that happened way back in the eighties, but the ripple effects are still being felt to this day. There's this concept in the law known as camouflaging bias. The idea is a judge takes a bribe in one case and then to avoid suspicion, punishes the hell out of other defendants so it looks like the judge is tough on crime. Then years later the defendant cries foul, says, hey, that wasn't fair. I got hit with this huge sentence because
this corrupt judge was covering his tracks. And that's what's happening in Chicago right now. Prisoners arguing that they too were victims of the corruption that Bob exposed, And so the story goes on. Some members of Bob's family really appreciate what he did for the city of Chicago. His brother Joe, who was an assistant US attorney, told me that he was proud of Bob's legacy, and his brother Dennis told me he gradually came to respect what Bob
had done. But it's been trickier with some of Bob's other siblings.
I mean, and I have a sister and another brother who want nothing to do with me. They want absolutely nothing to do with me. Why do you think that is because they believe what they saw that I'm some kind of a rat. I mean, why else would it be.
I spoke with both of the siblings Bob's referring to here, Tim and Diane. Both of them conveyed to me in so many words that they cared about Bob, but they'd never really been close with him. That even as a kid, Bob had been unscrupulous, hot headed, and full of himself. I talked about this at length with Tim Cooley. If you recall, Tim is the yoga instructor who lives in Vermont.
I don't know.
You know, why is Bob Bob?
You know I I've been thinking about it and and this may sound weird, but I don't know if Bob has ever felt loved. I've never known a loving relationship that he's been in. Actually, you know, he's had a lot of sex, I'm sure, but I don't think he's ever been in love. He's never had a relationship that I've ever been aware of, And so it's like he's looking for he's looking to fill that lack in some other ways.
Tim offered me a take on his brother that was neither rat nor hero, but something else altogether.
I'm afraid that.
That what matters most of all is just that he's known, that he's known, and the goodness is almost irrelevant. I'm sorry to say. The most important thing is that, look, I am a big man. Look I am somebody. I can do really horrible things, I can do good things. I'm somebody.
When I relayed all of this back to Bob, word for word, to my great surprise, Bob shrugged his shoulders and said he's right in a sense. In the year that I spent talking with Bob, he was always upbeat and quick to laugh. Part of this is just Bob's nature, but I think he was also kind of selling me on his story, as if to say, look at me, I live quite a life, didn't I? And he had.
But when I visited Bob in person and saw his cubby hole and the roommate who didn't really know him or cared to know him, I got a different feeling entirely. Bob's bravada was gone, and in its place was an air of defeat and almost disbelief, as if he couldn't quite fathom that this is how things had turned out. I asked Bob if there was any part of him that regretted what he'd done, if he could go back in time, would he have done it differently? Not flipped at all?
Absolutely, I mean absolutely. The day I put on that wire it was all over. I knew it was all over. I knew that, you know, my life could never be, But I never dreamed it would be as bad as God. I'm no better rop than some of those beggars out there in the street, and I'd better not even think about it, because again, it is the way it is. So I mean to say, I wish I could have changed that are you kidding me.
I mean, I'm trying to understand how you think about your own life. If the defining thing in your life is the thing you wish you hadn't done.
You've seen my life now. Think about that. You've seen my life now, and you can't understand how I wished I hadn't done that. That makes no sense.
Well, I understand it. It's not that I don't understand it.
I just.
Trying to wrap my head around it, that's all.
But you know, again, I don't know. I'm just saying that. There's no question in my mind. I'd be an idiot to say, gee, I'm glad that I, you know, destroyed myself, and that's what I wound up doing. I destroyed. Bob Cooley is no longer. This is not Bob Cooley name wise or even otherwise. What do you mean they left?
Bob Cooley was that person back there in Chicago that everybody came to when they had trouble and was able to help all kinds of people and be able to do whatever he damned pleased, never worried about getting arrested or getting parking tickets or anything whatever I wanted.
What is Bob Cooley.
Now just just to you know, somebody waiting to die. That pretty much sums it all up right now at this stage. I mean, they you kidding me? What is it? He's nobody, he's nothing.
Hearing him talk like this, I had to wonder once again why Bob had flipped in the first place. What had he been hoping for. There were so many different theories, and Bob himself kind of waffled on this question, offering different explanations on different days. It was to clean up the city, it was to heed the advice of his dying father. He was to stand up to Pat Marcy, who was a bully. And it's true Bob did not
like being pushed around. But my feeling about all of these was yeah, maybe, but they seemed like partial explanations at best. The theory I heard the most was that Bob owed to the mob. That's what was in all the papers at the time. But I don't really buy it. I mean, think about the timeline. Bob flipped back in nineteen eighty six, he fled town in nineteen eighty nine.
So put yourself in Bob's shoes if you were truly worried about owing money to the mob, and you were spooped that some goons were going to break your legs were worse, Why would you flip and then stick around town for the next three and a half years. You wouldn't. It's true Bob was a gambler, and I think that
this does in fact explain what he did. I kept thinking back to what Bob told me on the very first day that we talked, that he'd been walking down the street to get a Deli sandwich, he'd seen the Prosecutor's office and just walked in on an impulse. And now I could see it. Here's Bob the gambler, because walking into that office was, in some ways the biggest gamble of all. He was wagering his life. He was betting that he could almost magically save himself and perhaps
the city of Chicago while he was at it. Not a sensible bet, a real long shot, you might say, which is probably exactly why he did it. One day, toward the end of my visit with Bob, we had lunch together at the little place where I was staying. I ordered her some pizza, which we didn't finish, and I was about to throw the leftover slices out when Bob stopped me, no save those. He told me he wanted to feed the wildlife.
Why do you like to do it?
Because I've been doing it all my life pretty much. I like to feed the animals.
Why.
I'll be rewarded down the road for it.
It's always something for something.
I like you. I like animals. You know, I feel bad when I see him out there. You know they might be going hungry. It's always been my nature. I just do it.
We took the scraps of pizza and drove over to one of Bob's favorite spots. It was at the edge of a parking lot next to a strip mall. He came here often. This is kind of a random spot.
Why do you pick this spot?
We're like, we're at a over You'll see them all over here over on the other side. There, they've got a fast food restaurant, two fast food restaurants, and that's where the birds seem to migrate.
I stood there and watched as the birds flocked around him, swirling and chirping. For a moment, he seemed genuinely content. The whole scene reminded me of how back when he was still in Chicago, wearing a wire. He used to feed the baby raccoons with no ulterior motives, just a pure and simple act, a real rarity, because nothing in Bob's life was ever simple.
Your herds are up there at the corner, looks like yeah.
No, they for some reason, they always fly away and then they come back. But you'll get them cross the way over here and they'll come back and get it. The braver ones get fed the most. There's some of them coming up above.
Deep Cover is produced by Jacob Smith and Amy Gaines and edited by Karen Chakerji. Our senior editor is Jen Guera. Original music and the deep Cover theme was composed by Luis Garra, with performances by Luise Audrian Terrasas, Alan Fajardo, Mi Longoria, and Jimmy Messer. Flawn Williams is our engineer. Our art this season was drawn by Cheryl Cook and designed by Sean Carney. Mia Lobel is our executive producer.
Special thanks to Heather Fain, John Schnarz, Carly Migliori, Maya Caning, Christina Sullivan, Eric Sandler, Mary Beth Smith, Brant Haynes, Maggie Taylor, Nicole Morano, Megan Larson, Morgan Ratner, Royston Deserve, Lucy Sullivan, Edith Russello, Riley Sullivan, Jen Sanchez, Jason Gambrell, Martin Gonzalez, and Jacob Weisberg. Additional special thanks to Jill Gillette, Travis Dunlap, Maggie de Poy, Bill Hogan, David Grossman, Mike Shephard, Jim Wagner,
Denny Cherrillo, Lisa Chase Patterson, and Michael Deutsch. Also Christian McNally, Isabel Vasquez, Jesse de Bartolomeo, Jane Miliotis, Sarah Kraditch, and the National Archives at CHU Chicago. I'm Jake Halbert. If you like this season of deep Cover, then you should really check out our first season, The Drug Wars, which tells the story of an FBI agent who goes under cover with a biker gang and uncovers a series of clues that leads to a war, I mean, a full
scale invasion. Also check out Pushkin's other true crime podcasts, Lost Hills and Bad Women. These shows and more are available ad free for Pushkin Plus subscribers. To find more Pushkin podcasts, listen on the iHeartRadio app, Apple Podcasts, or wherever you listen to podcasts,