Episode 1: The Walk-In

For all intents and purposes, the man named Bob Cooley died decades but in reality, Bob, he's still very much alive. So your neighbors have no idea who you are. Oh no, certainly not. Does that work out for the best? No, no big thing either way. It's not a big thing either way. It's just that you know, and they wouldn't believe it. If you know, if I told my story, people wouldn't normally believe it. That's Bob. I've been interviewing him for the past year, mainly by zoom, but recently

I visited him in person. He lives in this small ranch house at the edge of a vast desert somewhere in the American Southwest. I can't tell you the name of the town or even the state where he lives. And that's for Bob's own safety, all right. I got more on the floor than that kind in here. Bob's now in his late seventies. He has thick glasses and

a strong jaw dotted with gray's stubble. When we met, he was wearing an old La Dodgers cap and a T shirt that said Parental Advisory Explicit Content, like the labels they used to put on CDs. The house where Bob lives isn't his. He just rents a room in it. I'll show you in my room beside his bed, the floor is cluttered with vats of V eight vegetable juice and cylinders of pringles. Sort of looks like he's preparing for a hurricane. Obviously, it's a very small room, but

it's got a bed that's for I sleep well. So are all your worldly possessions in this room? Oh? Yeah, that's it. It wasn't always like this for Bob. Back before he vanished, before we ran for it, Bob lived a very different life. He was a big time lawyer in Chicago. I used to run around with thousands of dollars in my pocket and pick up everybody's checks and whatever. I would buy the most expensive thing, thinking it was

the best. Bob drove around in a gleaming convertible, wore a hefty gold chain, partied at the nightclubs on Rush Street, gambled with the bookies, and dined out with the city's judges. But that was then. Today he survives on Social Security and lives in this tiny room at the edge of the desert, basically in hiding. Did you do you have any of your old IDs that you had under your fake names? Oh? Yeah, can you show them to me? Bob leads me over to his closet and pulls out

a big stack of IDs and credit cards. It looks like what you might find at the Lost and Found at a ballpark. The name varies on each of these, but the face is the same, just a little older. Each time. Bob points at one id, an old driver's license. He died about ten years ago. That's you, that's a different one. Why did he die ten years ago? He had Apparently he must have had an unfortunate an accent or something. He suddenly disappeared from the face of the earth.

Here's another that's a fourth name. What happens to this guy? Yeah, he had an accident too. A lot of these guys had some very bad accents. And that's how it goes with Bob. He assumes one identity for a few years, pretending to be some guy in some random town, until Bob feels that itch like he's not safe. Then that guy dies, the id gets tossed in this pile, and Bob becomes someone else. And let me assure you, there is a reason for all of this paranoia, very good reason,

a backstory that explains it all, a saga. Really. Back in his heyday, when Bob Cooley was still Bob Cooley, he was the man in Chicago. People were downtown knew him as a high priced criminal defense lawyer, but to the city's gangsters, to the mob, he was much more than this. He was their guy, their insurance policy. Sure he could argue a case well enough, but if need be, he could also fix a case, place the right bribe with just the right judge, and get precisely the right verdict.

He was like a get out of jail free card, only his services weren't free. And Bob he was more than just a hired hand. He was part of an elite cadre of men. They were backed by the Mob or the Chicago Outfit as it's known. They basically ran the city of Chicago. Their powerbase was the First Ward, one of the city's most powerful districts. It was a political machine run by gangsters. They had complete control over the Sheriff's Department, the Attorney General's office, the police department,

all the courts. They controlled absolutely everything. So mobsters realized if they did anything, they had absolute protection for it. Bob Cooley did the bidding of the First Ward and the Outfit for almost a decade, until one day in the spring of nineteen eighty six when he decided to betray them. He just walked into a prosecutor's office and started talking. I regret having walked into that man's office like I did, probably the worst regret of my life.

But nothing I can do about that. I jumped off the building. It's a decision that, even now, thirty five years later, still baffles people. Why did he do it? People are still arguing about this, not just that there are court cases going on right now where they're discussing what Bob did. And how old were you when the shooting which resulted in your incarceration. Crew was eighteen years old. There are guys in prison hoping to get out by

invoking Bob's name and the secrets he revealed. Bob's legacy is still shrouded in controversy. But here's one thing that most people can agree on. After Bob Cooley flipped, the city of Chicago was never quite the same. I'm Jake Halbern and this is Deep Cover, Season two, mob Land, Episode one, The Walking. So I've been fascinated by mob stories ever since I was a kid. I must have watched The Untouchables about one hundred times. Maybe you've seen it.

It's set in nineteen thirty Chicago. Robert de Niro plays al Capone, the villain, and Kevin Costner plays Elliott Ness, the clean cut law man. You know, this is generally how it goes with these films. It's the old Cops and Robbers theme. Two sides at war with one another. Fuck you got nothing, Yeah, because you've got nothing. You got nothing at caught, you not got the bookkeeper, you got nothing. From the outset, it was clear to me that Bob Cooley's story didn't fit neatly into this genre.

From the moment that Bob walked into that prosecutor's office that day offered to betray the mob, he was essentially at war with himself, and in Bob's heyday, back in the seventies and eighties, the Chicago Mob was still plenty powerful. I heard stories about this from a whole bunch of people, but one of them in particular stands out. A woman

named Marie Dyson told it to me. She'll eventually play an important role in our story, but right now, all you need to know is that back in the early eighties, Marie was a young FBI agent based in Chicago, and one day she got a little tutorial on how Chicago really worked. A guy laid it all out for her, and that lesson, she says, it came from a mob hit man who at the time was in custody. I remember he had real pretty eyes, and I thought, oh,

this guy's smooth as silk. You know again, I'm sitting there thinking, you know, at any point in time, he can come across this table and I'm a goner. This guy had killed many, many, many people, and he just looked at me like what is your problem. You know, this is the way we do it. And I can do anything I want to do because I have an attorney that will pay any judge take care of every case I have, so I can kill anybody I want to kill. He was breaking. You know. This is the

way it works, This is how it operates. This is how we get things done. The hitman said he had this attorney who could pay any judge to get him out of any jam. This hitman wasn't talking about Bob Cooley explicitly, but he could have been, because that's precisely the kind of thing that Bob did, and did very well, that is, until he switched sides and then vanished. I should tell you I'm not the first reporter to chat with Bob. Over the years. He's done a few interviews

and even written a memoir. Every once in a while, Bob Cooley just kind of pops up in Virginia or Colorado or some town in the Southwest and then vanishes again, like some kind of mystical prairie dog. Some people told me that he'd gone into the witness protection program, but that wasn't true. Bob was just really good at disappearing. This meeting is being recorded. Okay. I first connected with Bob about a year ago. In fact, before Bob and I could really get started, we had I guess you'd

call it some technical difficulties. There was a dog at his house and it just would not stop barking. Hey, Bob, I'm sorry to interrupt, but is there anything we can think about with the dog, because I worry if the dog keeps up, I'm not going to be able to use some of the tape. Is there any way to get him in a different part of the house or anything like that. He wasn't being serious. Bob actually loves animals. He lives with five dogs, two cats, and he loves

feeding birds to pass the time. In any case, Bob took the dog outside. We continued, and pretty soon he was telling me about that day back in March of nineteen eighty six when he made his big decision to switch sides and betray the Mob. It was a Saturday. He was out for a stroll in downtown Chicago, right by the Federal Courthouse. Yes, I remember it. I was going to get a sandwich in something. I have no idea what it was. Something just said to me, I'm going to go up there, and let's go up there

and let's see who is up there. There was nobody around. When he says up there, he means the eighth floor of the Federal Courthouse that was the home of the Organized Crime Strike Force, the prosecutors who went after the mob. Bob says he walked in on an impulse, just saw the empty building and thought, do this. I went in there and went upstairs to the strike for us and you know, knock on the door, and I go in, and you know, I'd like to talk to somebody here.

And that somebody was a government attorney named Gary Shapiro, and he introduced himself. You know, I'm the head of the Strike for us, and I'm sure he was shocked. You know, I'm sure he knew who I was. You know, prior to that, I didn't know Bob Cooley from a man in the moon. So when I first saw him, I had no idea what to expect. As a prosecutor charged exclusively with going after the mob, Gary had a really, really hard job. It was nearly impossible to get anyone

to testify against the city's gangsters. Gary says that some years seemed like there was a mob killing almost every week. In fact, Gary's first big case involving the mob fell apart when his star witness was murdered on the eve of trial. In any case, when Bob first walked into his office, Gary was intrigued but not exactly impressed. Well, I hope Bob doesn't take this personally, but he's a schlub. Bob is you know he's not. He's not impressive in

terms of the way he presents himself. I don't remember if he was wearing his you know, his turtleneck and gold chains, but he probably was. Turns out this was actually a point of pride for Bob. Everybody had to wear a tie in Chicago, every lawyer, I should say, every lawyer except me. This super casual look was like Bob's dress code. No fancy suit, no tie, just a gold chain. This was all part of his branding, bling casual. I guess you could call it Gary Shapiro. He didn't

know what to make of this. He's kind of shambling and he doesn't speak like a lawyer. You'd never think Bob Cooley was an attorney, and that's kind of way he present he himself. He was just this guy who came into my office completely unimpressive, and sat down and started telling me about the root of all evil, which

was gambling. Illegal gambling. That's what Bob had come in to talk about initially, anyhow, and he seemed to know an awful lot about how it all worked, how the lion's share of the mob's profits came from illegal gambling, and this money funded all kinds of illegal activity, including public corruption. And look, we're not talking about a petty bribe here and there. Back in the nineteen eighties, Chicago

was one of the most corrupt cities in America. Gary was a mob specialist, so he knew a lot of this already. He mainly just sat and listened and Bob he went on to explain that he himself was a big gambler and he was really good at it, but he'd seen what happened to the guys who lost, how

those guys basically became slaves to the mob. You had certain paper would have a gambling debt, Judges, politicians, others who would gamble and lose a lot of money, and they were in fear of being killed or being beaten or whatever by the mob. And that's how the mob would wind up recruiting a lot of people. That's what I was talking to him about. Bob would tell Gary that he knew the mob intimately, that he was connected to corrupt elected officials, judges, and Alderman, even a state senator.

Bob claimed to be at the center of all this and he was tired of it that he wanted to clean up the whole system. Now here's the really weird part. Bob was offering his services, but he didn't ask for anything in return. In fact, he says he made just one request. Bob wanted to confirm that he himself was not currently under investigation. Why, Bob claimed it was to protect his own reputation so he'd be credible if he became a witness for the FEDS. I would never cooperate

or burn somebody taking help myself. I never would do that. I detested stool pigeons and people that you would sell out their friends and whatever to help themselves. I would never have done that. Bob says he didn't want anyone to say years from now that he was out to save his own skin. Gary, meanwhile, wasn't sure about what had just landed in his lap. He was a prosecutor. When he worked with informants, it was always after the cops or the FBI had vetted them. That was the

proper order of things. For some reason, Bob had come directly to Gary. Why wasn't so clear, But there had to be a reason, right. The meeting ended as it began, rather mysteriously. Gary basically said, we'll be back in touch, and then Bob stood up and walked out the door. So there was Gary in his short sleeves Saturday, kind of wondering what the hell just happened. It was intriguing, for sure, but something seemed fishing. From my perspective, Bob

was too good to be true. And so all of your antennae are out and you're worried about you know, why have the gods delivered this gift to me? There's got to be something wrong with this. I had profound questions about his motivation, and I get it. I felt the exact same way when Bob told me this story, And from Gary's perspective, there were a few things about this whole encounter that were more than a little puzzling. Obviously, Bob knew the dangers of talking to the FEDS, so

why would Bob take the risk? I mean, he didn't seem to be on the run from the mob, and he didn't seem to be in trouble with the law either. So was Bob for real? I thought the more realistic possibility that this was another job who had a Messiah clomplex. And yet, I mean, I'm not going to turn down the Messiah. I'm not going to say no to the Messiah. Bob walked out of Gary's office under the streets of downtown Chicago and began to take stock of the situation.

Once I made the step, I could not undo that. And you know, as I said, in an hour, after a minute, probably after I started talking to Gary, I regretted doing what I did. I regretted coming in there. I was mad at myself again, and you know again, couldn't understand why I did it. You know, I just couldn't. He felt like he'd thrown it all away. Everything he'd worked for. Bob had started off as a cop walking the beat, scraped his way through law school, slowly built

up a successful practice as a criminal defense lawyer. He was known throughout the city no tie, gold chain Bob. He drove around in a big Chrysler that looked a bit like a Limo. For a few years, he owned a health club and was also part owner of an Italian restaurant called Greco's. He'd worked hard to gain the confidence of many powerful men, from respected judges to mob captains, so why risk all of that now? Suddenly it seemed rash crazy. Even Bob began to hope that maybe Gary

Shapiro would see it this way too. I'm hoping this guy thought I was some kind of a nut and I wasn't going to call him. I was not going to call him or talk to him, or stop in to see him. And I'm hoping that nobody comes, you know, nobody comes to see me. And I'm even thinking, initially, well, if somebody comes, I'm gonna tell him. I changed my mind. Bob just hoped that Gary didn't talk to anyone with

loose lips. The trick now was acting normal, just go about with my life and hoping that I wouldn't suddenly have somebody come up and shoot me in the back of the head. The one person who may have picked up on Bob's jitters was Judy d'angelus, Bob's secretary slash paralegal slash office manager. She was in her twenties, young and wide eyed. Judy she knew Bob about as well as anyone did. We were friends. I mean, I was never a girlfriend of his. I think I was the

only secretary to say. And he'll admit that. Judy and Bob had a kind of instant synergy. Bob says that he trusted her from the moment he first met her. I met Judy when she was in a grocery store, just in talking to her like a very sharp girl. So I suggested, you would you want to come to work for me? And you know, oh yeah, sure, I'd love it. Whatever I mean. She had obviously no experience in the legal field, nothing like that, and I put

her in charge of my whole office. Wait, what made you think, Like you met this random woman at a grocery store, Like, what makes you what made you think that she would be the right to run your whole office? I have no idea take, I don't know why, it just it just came to me. Judy knew that Bob was a big gambler. Bob bet on sports games mainly.

He used a bunch of different bookies and these guys you had to pay or work out some kind of arrangement because almost all of them were backed by the mob, so you didn't want to get too deep in the hole. But for Bob, gambling was a way of life. I think he loved the the actual act of gambling and you know, getting it right. I think Bob will tell you the same thing that he was not motivated by me, but boy, if he had it, he spent it, and then if he didn't have it, he'd go out and

find more. This is part of what made Bob such an exciting guy to know. He was a whirlwind of activity, and sometimes Judy loved getting swept up in it all. So did her then boyfriend now husband. They both told me Bob treated them like family. He would buy them dinner, take them out for nights on the town, get their parking tickets fixed. Bob was like their mobbed up fairy godfather, sprinkling magic dust wherever they went. But there were other

moments when they caught glimpses of Bob's darker dealings. They didn't ask too many questions, but they understood the lurking dangers and this particular week, even though Judy didn't know all the details of what was going on with Bob, she knew enough to worry. I was spiritful for Bob's life. I would come into the office in the morning, and if he didn't call me right away, I didn't know if he was in a trunk somewhere dead. And I

was careful about his gambling. I used to spend hours and hours checking different things, checking odds, checking numbers, checking power ratings, checking all these things. I didn't do it that week. That week, he means, the week he visited Gary, the week his life started to unravel. That week, he says, he dispensed with his usual precautions, gambled recklessly, placed several impulsive bets, and ultimately lost man. I had three or four of the worst days of my life gambling. Everything

I'm doing is wrong. I'm losing I'm losing this, I'm losing that. And by now later in the week, I realized I go like one hundred and it was like one hundred ten, one hundred and twenty thousand dollars. You you kind of lost your cool a little bit, Oh, no question about it. Bob's concerns about his debts were compounded by his gnawing feeling that he hadn't seen the last of Gary Shapiro, that by walking into Gary's office, he'd put something much bigger into motion, thinking what did

I do? You know? What did I do? And again I was hoping against hope that okay, that'll be the end of it. But I knew that wasn't going to be the case. I mean, I knew I'd be getting a visit. I didn't know when, but I knew I'd be getting a visit. Then one morning it happened. I walked into the office and that Judy was behind the desks, and Judy said to me, I think there's some FBI agents here to see you. In the moment she said

that I knew exactly what it was. It was the thing he'd been dreading, the very thing he himself had set in motion coming right back at him for FBI agents on his doorstep, and they had questions. One of the FBI agents to visit Bob that day was Marie Dyson. Marie was in some ways an unlikely agent. She joined the bureau kind of on a whim after her dad

suggested that she apply, and that began the process. And then I went to Quantico like everybody else for four months training, had no idea what I was getting myself into. Marie didn't want to mess this up. She was a young woman, a real rarity in the bureau. Around the time that she joined, only two percent of FBI agents were women, and Marie she felt that, Wow, you've entered a man's world. You know, we can make mistakes, we can screw up. Everybody laughs about it, but y'all don't

have that luxury. You know you cannot make a mistake. And I will speak personally for myself, but I think I kind of felt like, well, we need to prove ourselves that we can do the job. She was sent to Chicago in nineteen eighty one, where she was assigned to the public Corruption squad, and she quickly learned the mob playbook. The evidence is going to get tainted or thrown away. Any eyewitnesses will take care of them, you know, they'll be eradicated, and then the judge will be taken

care of. And it was a way of life, It's how it operated. The mob was teflon. So Marie shows up at Bob's office with three other agents, all of them guys. We walked in and set in Bob's office, and he was not very happy about this. And he looked around and he said, you all look like FBI agents except for the girl. And he always said that he would say that, you know, thereafter, because I don't know what an FBI agent female was supposed to look like.

But he didn't think I look like one, which seemed to relieve him a little bit. Marie and these other agents had managed to piece together some limited info on who Bob was. They knew, for example, that he wasn't the target of any ongoing investigations, so he was in no imminent legal trouble, which raised the question why had Bob come in? It was not commonplace. It was very suspicious. That's how we looked at it in the beginning. Marie's colleague,

Steve Bowen, shared her skepticism. He was there that day too. Marie and Steve were pretty close. They actually drove to work together. Yeah, they were carpool buddies. Steve was a former cop from Indianapolis who had entered the FBI at thirty five, which was the cutoff for joining, and that must have made him just about the oldest rookie in the bureau. So in a way, Steven streetwise, but in other important ways he was very green. I've only been

an agent two years. I've got no Chicago Mob background. I don't know who the players are. They dropped names that would mean absolutely netting to me. He might have been green, but he knew enough to realize just how rare it was to have a guy like Bob Cooley show up and offer to help. Started kidding me unheard of. It just doesn't happen for someone just to walk in out of the blue. Why is he doing this? I mean, he's literally putting his life on the line, and I honestly,

I think it caught everybody with their pants down. We didn't know how to handle it at first, and that's really why Steve and Marie visited Bob that day to get a handle on things. You've got an attorney that we really wan't familiar with. We didn't know how high up in the mob he was, if he was at all, So we just had to start setting up meetings with him and talk to him and trying to get a feel for what he's doing, where is coming from, what's wrong with him? If anything? Is he a plan? Is

he a double age. What is he? You couldn't really figure out a guy like Bob and just one sitting or even three for that matter. So this was actually the first of many meetings that Steve and Marie had with Bob. They had to vet him, much the way the CIA would have to vet a Soviet defector who just walked in off the street. And Bob he understood this Steve and those others for a long time after I came in, I knew they didn't believe me, and I knew that they were waiting. You know, they felt

there something wrong. But you know what was I to say? I mean, I knew that just based on certain reactions from them, and the best of it. After that first meeting at Bob's office, they met elsewhere at a hotel where no one would see what they were up to, and gradually, over a series of meetings, Bob started talking, and once he did, he didn't stop. Bob could give us judges, lawyers, police officers, court personnel, politicians, He could

give us those people. It was like, after having all those jitters, he just leaped into the deep end, no looking back. He started laying out the details of his story that he was a powerbroker for the city's notorious First Ward. Technically, the First Ward was just one of Chicago's fifty legislative districts, but it was one of the most powerful and rumored to be among the most corrupt. A political machine run by gangsters, and Bob claimed to

be their lawyer, their fixer, a trusted confidant. We controlled the courts, We controlled the States Attorneys Office, We control the police Department. We controlled that absolutely everything. Okay, so he's bragging a bit. They didn't control absolutely everything, but they controlled an awful lot. Bob was and still is a natural storyteller, and he presented himself as the good guy, the hero who'd fallen in with the wrong crowd and now wanted to make amends. He had a whole mythology

about himself. Most of it was to put himself in a good light and to protect himself. He was street savvy. He was a survivor. You understood that. I mean, you just can't be a real straight up on his guy and survived with this. Bob knew how to keep himself alive, and he could excuse me bullshit with the best. It all came down to the old bullshit meter. I asked Steve Bowen about this, Did you have a gut feeling

about him? No, and that's what was disturbing. I didn't see your tone is all this and you want nothing for it. You're not really looking for anything. You're looking for money. We tried to get a figure out. I mean, what do you want? What are you doing? He says, I'm just tired of it. I'm just I don't know what happened to change his mind to bring him forward, and to this day, I still don't. Bob did want one thing. He made one request. I had asked the agents,

I'm asking you to do me one favor. What's that If I get killed, you let everybody know. I wasn't doing it because out of fear of the mob or or as basically as a stool pigeon. I had come forward and I was doing the right thing to clean up the system. I asked a couple of the agents that, oh, certainly I was. I was scared stiff, but I had a mission. Was this was my mission. I've spent the last year digging deep into Bob's story, talking to people who knew him back in the day, which was a

whole cast of characters. Because Bob rubbed shoulders with just about everybody. Judges, politicians, bookies, gangsters, cops, and hitmen. They all confided in him. Bob was a keeper of their secrets. Secrets had implicated not just a few powerful men, but a whole shadowy realm, a black market of corruption where politicians were bought and justice was sold, where for the

right price, even murderers could walk free. Bob was privy to all of it, and he kept it under wraps until the spring of nineteen eighty six, when he started to talk up on season two of Deep Cover. For approximately five years, a Chicago lawyer has been a government informant, secretly recording conversations with some of this city's movers and shakers. The identity of this informant will come as a shock

to some powerful people. I can say with all certainty, I think he's a hero because he didn't have to do what he did, and he did it anyway. Well, I can see how people would think that, Yeah, because Cooley is very manipulate too. But he just sort of got away with murder and he said, don't ever tell us what to do. He said, nobody wears a wire in US and lives to talk about it. Deep Cover is produced by Jacob Smith and Amy Gaines and edited

by Karen Shakerji. Our senior editor is Jan Guera. Original music in our theme was composed by Louis Gara and Fawn Williams as our engineer. Our art this season was drawn by Cheryl Cook and designed by Sean Carney Mia

Lobell as our executive producer. Special thanks to Heather Fame, John Schnars, Carl Mcliori, Maya Caning, Christina Sullivan, Eric Sandler, Mary Beth Smith, Brant Haynes, Maggie Taylor, Nicole Morano, Megan Larson, Royston Baserve, Lucy Sullivan, Edith Russlo, Riley Sullivan, Jason Gambrell, Martin Gonzalez, and Jacob Weissberg. I'm Jake Halbern. Pleasure Us. If you want to learn more about Bob Cooley's story, you can check out his memoir, published in two thousand

and four. It's called When Corruption Was King. Bob co wrote it with Hill l Levin. Subscribe to pushkin Plus and you can binge the rest of the season right now. Adds free. Find pushkin Plus on the deep Cover Show page in Apple Podcasts or at pushkin dot fm. To find more Pushkin podcasts, listen on the iHeartRadio app, Apple Podcasts, or wherever you listen to podcasts.