Speaker 1: Pushkin Jake Alpern here Before we get started, I wanted
Speaker 1: you to know that deep Cover Season two will be
Speaker 1: dropping weekly on Mondays, but the full season is available
Speaker 1: right now ad free for Pushkin Plus subscribers. That's all
Speaker 1: ten episodes right away. Fine Pushkin Plus on the deep
Speaker 1: Cover show page in Apple Podcasts, or at Pushkin dot Fm.
Speaker 1: Here's the first thing I need to tell you about
Speaker 1: Robert Coolly. Officially, legally, he no longer exists. He's a ghost.
Speaker 1: For all intents and purposes, the man named Bob Cooley
Speaker 1: died decades but in reality, Bob, he's still very much alive.
Speaker 1: So your neighbors have no idea who you are. Oh no,
Speaker 1: certainly not. Does that work out for the best? No,
Speaker 1: no big thing either way. It's not a big thing
Speaker 1: either way. It's just that you know, and they wouldn't
Speaker 1: believe it. If you know, if I told my story,
Speaker 1: people wouldn't normally believe it. That's Bob. I've been interviewing
Speaker 1: him for the past year, mainly by zoom, but recently
Speaker 1: I visited him in person. He lives in this small
Speaker 1: ranch house at the edge of a vast desert somewhere
Speaker 1: in the American Southwest. I can't tell you the name
Speaker 1: of the town or even the state where he lives.
Speaker 1: And that's for Bob's own safety, all right. I got
Speaker 1: more on the floor than that kind in here. Bob's
Speaker 1: now in his late seventies. He has thick glasses and
Speaker 1: a strong jaw dotted with gray's stubble. When we met,
Speaker 1: he was wearing an old La Dodgers cap and a
Speaker 1: T shirt that said Parental Advisory Explicit Content, like the
Speaker 1: labels they used to put on CDs. The house where
Speaker 1: Bob lives isn't his. He just rents a room in it.
Speaker 1: I'll show you in my room beside his bed, the
Speaker 1: floor is cluttered with vats of V eight vegetable juice
Speaker 1: and cylinders of pringles. Sort of looks like he's preparing
Speaker 1: for a hurricane. Obviously, it's a very small room, but
Speaker 1: it's got a bed that's for I sleep well. So
Speaker 1: are all your worldly possessions in this room? Oh? Yeah,
Speaker 1: that's it. It wasn't always like this for Bob. Back
Speaker 1: before he vanished, before we ran for it, Bob lived
Speaker 1: a very different life. He was a big time lawyer
Speaker 1: in Chicago. I used to run around with thousands of
Speaker 1: dollars in my pocket and pick up everybody's checks and whatever.
Speaker 1: I would buy the most expensive thing, thinking it was
Speaker 1: the best. Bob drove around in a gleaming convertible, wore
Speaker 1: a hefty gold chain, partied at the nightclubs on Rush Street,
Speaker 1: gambled with the bookies, and dined out with the city's judges.
Speaker 1: But that was then. Today he survives on Social Security
Speaker 1: and lives in this tiny room at the edge of
Speaker 1: the desert, basically in hiding. Did you do you have
Speaker 1: any of your old IDs that you had under your
Speaker 1: fake names? Oh? Yeah, can you show them to me?
Speaker 1: Bob leads me over to his closet and pulls out
Speaker 1: a big stack of IDs and credit cards. It looks
Speaker 1: like what you might find at the Lost and Found
Speaker 1: at a ballpark. The name varies on each of these,
Speaker 1: but the face is the same, just a little older.
Speaker 1: Each time. Bob points at one id, an old driver's license.
Speaker 1: He died about ten years ago. That's you, that's a
Speaker 1: different one. Why did he die ten years ago? He
Speaker 1: had Apparently he must have had an unfortunate an accent
Speaker 1: or something. He suddenly disappeared from the face of the earth.
Speaker 1: Here's another that's a fourth name. What happens to this guy? Yeah,
Speaker 1: he had an accident too. A lot of these guys
Speaker 1: had some very bad accents. And that's how it goes
Speaker 1: with Bob. He assumes one identity for a few years,
Speaker 1: pretending to be some guy in some random town, until
Speaker 1: Bob feels that itch like he's not safe. Then that
Speaker 1: guy dies, the id gets tossed in this pile, and
Speaker 1: Bob becomes someone else. And let me assure you, there
Speaker 1: is a reason for all of this paranoia, very good reason,
Speaker 1: a backstory that explains it all, a saga. Really. Back
Speaker 1: in his heyday, when Bob Cooley was still Bob Cooley,
Speaker 1: he was the man in Chicago. People were downtown knew
Speaker 1: him as a high priced criminal defense lawyer, but to
Speaker 1: the city's gangsters, to the mob, he was much more
Speaker 1: than this. He was their guy, their insurance policy. Sure
Speaker 1: he could argue a case well enough, but if need be,
Speaker 1: he could also fix a case, place the right bribe
Speaker 1: with just the right judge, and get precisely the right verdict.
Speaker 1: He was like a get out of jail free card,
Speaker 1: only his services weren't free. And Bob he was more
Speaker 1: than just a hired hand. He was part of an
Speaker 1: elite cadre of men. They were backed by the Mob
Speaker 1: or the Chicago Outfit as it's known. They basically ran
Speaker 1: the city of Chicago. Their powerbase was the First Ward,
Speaker 1: one of the city's most powerful districts. It was a
Speaker 1: political machine run by gangsters. They had complete control over
Speaker 1: the Sheriff's Department, the Attorney General's office, the police department,
Speaker 1: all the courts. They controlled absolutely everything. So mobsters realized
Speaker 1: if they did anything, they had absolute protection for it.
Speaker 1: Bob Cooley did the bidding of the First Ward and
Speaker 1: the Outfit for almost a decade, until one day in
Speaker 1: the spring of nineteen eighty six when he decided to
Speaker 1: betray them. He just walked into a prosecutor's office and
Speaker 1: started talking. I regret having walked into that man's office
Speaker 1: like I did, probably the worst regret of my life.
Speaker 1: But nothing I can do about that. I jumped off
Speaker 1: the building. It's a decision that, even now, thirty five
Speaker 1: years later, still baffles people. Why did he do it?
Speaker 1: People are still arguing about this, not just that there
Speaker 1: are court cases going on right now where they're discussing
Speaker 1: what Bob did. And how old were you when the
Speaker 1: shooting which resulted in your incarceration. Crew was eighteen years old.
Speaker 1: There are guys in prison hoping to get out by
Speaker 1: invoking Bob's name and the secrets he revealed. Bob's legacy
Speaker 1: is still shrouded in controversy. But here's one thing that
Speaker 1: most people can agree on. After Bob Cooley flipped, the
Speaker 1: city of Chicago was never quite the same. I'm Jake
Speaker 1: Halbern and this is Deep Cover, Season two, mob Land,
Speaker 1: Episode one, The Walking. So I've been fascinated by mob
Speaker 1: stories ever since I was a kid. I must have
Speaker 1: watched The Untouchables about one hundred times. Maybe you've seen it.
Speaker 1: It's set in nineteen thirty Chicago. Robert de Niro plays
Speaker 1: al Capone, the villain, and Kevin Costner plays Elliott Ness,
Speaker 1: the clean cut law man. You know, this is generally
Speaker 1: how it goes with these films. It's the old Cops
Speaker 1: and Robbers theme. Two sides at war with one another.
Speaker 1: Fuck you got nothing, Yeah, because you've got nothing. You
Speaker 1: got nothing at caught, you not got the bookkeeper, you
Speaker 1: got nothing. From the outset, it was clear to me
Speaker 1: that Bob Cooley's story didn't fit neatly into this genre.
Speaker 1: From the moment that Bob walked into that prosecutor's office
Speaker 1: that day offered to betray the mob, he was essentially
Speaker 1: at war with himself, and in Bob's heyday, back in
Speaker 1: the seventies and eighties, the Chicago Mob was still plenty powerful.
Speaker 1: I heard stories about this from a whole bunch of people,
Speaker 1: but one of them in particular stands out. A woman
Speaker 1: named Marie Dyson told it to me. She'll eventually play
Speaker 1: an important role in our story, but right now, all
Speaker 1: you need to know is that back in the early eighties,
Speaker 1: Marie was a young FBI agent based in Chicago, and
Speaker 1: one day she got a little tutorial on how Chicago
Speaker 1: really worked. A guy laid it all out for her,
Speaker 1: and that lesson, she says, it came from a mob
Speaker 1: hit man who at the time was in custody. I
Speaker 1: remember he had real pretty eyes, and I thought, oh,
Speaker 1: this guy's smooth as silk. You know again, I'm sitting
Speaker 1: there thinking, you know, at any point in time, he
Speaker 1: can come across this table and I'm a goner. This
Speaker 1: guy had killed many, many, many people, and he just
Speaker 1: looked at me like what is your problem. You know,
Speaker 1: this is the way we do it. And I can
Speaker 1: do anything I want to do because I have an
Speaker 1: attorney that will pay any judge take care of every
Speaker 1: case I have, so I can kill anybody I want
Speaker 1: to kill. He was breaking. You know. This is the
Speaker 1: way it works, This is how it operates. This is
Speaker 1: how we get things done. The hitman said he had
Speaker 1: this attorney who could pay any judge to get him
Speaker 1: out of any jam. This hitman wasn't talking about Bob
Speaker 1: Cooley explicitly, but he could have been, because that's precisely
Speaker 1: the kind of thing that Bob did, and did very well,
Speaker 1: that is, until he switched sides and then vanished. I
Speaker 1: should tell you I'm not the first reporter to chat
Speaker 1: with Bob. Over the years. He's done a few interviews
Speaker 1: and even written a memoir. Every once in a while,
Speaker 1: Bob Cooley just kind of pops up in Virginia or
Speaker 1: Colorado or some town in the Southwest and then vanishes again,
Speaker 1: like some kind of mystical prairie dog. Some people told
Speaker 1: me that he'd gone into the witness protection program, but
Speaker 1: that wasn't true. Bob was just really good at disappearing.
Speaker 1: This meeting is being recorded. Okay. I first connected with
Speaker 1: Bob about a year ago. In fact, before Bob and
Speaker 1: I could really get started, we had I guess you'd
Speaker 1: call it some technical difficulties. There was a dog at
Speaker 1: his house and it just would not stop barking. Hey, Bob,
Speaker 1: I'm sorry to interrupt, but is there anything we can
Speaker 1: think about with the dog, because I worry if the
Speaker 1: dog keeps up, I'm not going to be able to
Speaker 1: use some of the tape. Is there any way to
Speaker 1: get him in a different part of the house or
Speaker 1: anything like that. He wasn't being serious. Bob actually loves animals.
Speaker 1: He lives with five dogs, two cats, and he loves
Speaker 1: feeding birds to pass the time. In any case, Bob
Speaker 1: took the dog outside. We continued, and pretty soon he
Speaker 1: was telling me about that day back in March of
Speaker 1: nineteen eighty six when he made his big decision to
Speaker 1: switch sides and betray the Mob. It was a Saturday.
Speaker 1: He was out for a stroll in downtown Chicago, right
Speaker 1: by the Federal Courthouse. Yes, I remember it. I was
Speaker 1: going to get a sandwich in something. I have no
Speaker 1: idea what it was. Something just said to me, I'm
Speaker 1: going to go up there, and let's go up there
Speaker 1: and let's see who is up there. There was nobody around.
Speaker 1: When he says up there, he means the eighth floor
Speaker 1: of the Federal Courthouse that was the home of the
Speaker 1: Organized Crime Strike Force, the prosecutors who went after the mob.
Speaker 1: Bob says he walked in on an impulse, just saw
Speaker 1: the empty building and thought, do this. I went in
Speaker 1: there and went upstairs to the strike for us and
Speaker 1: you know, knock on the door, and I go in,
Speaker 1: and you know, I'd like to talk to somebody here.
Speaker 1: And that somebody was a government attorney named Gary Shapiro,
Speaker 1: and he introduced himself. You know, I'm the head of
Speaker 1: the Strike for us, and I'm sure he was shocked.
Speaker 1: You know, I'm sure he knew who I was. You know,
Speaker 1: prior to that, I didn't know Bob Cooley from a
Speaker 1: man in the moon. So when I first saw him,
Speaker 1: I had no idea what to expect. As a prosecutor
Speaker 1: charged exclusively with going after the mob, Gary had a really,
Speaker 1: really hard job. It was nearly impossible to get anyone
Speaker 1: to testify against the city's gangsters. Gary says that some
Speaker 1: years seemed like there was a mob killing almost every week.
Speaker 1: In fact, Gary's first big case involving the mob fell
Speaker 1: apart when his star witness was murdered on the eve
Speaker 1: of trial. In any case, when Bob first walked into
Speaker 1: his office, Gary was intrigued but not exactly impressed. Well,
Speaker 1: I hope Bob doesn't take this personally, but he's a schlub.
Speaker 1: Bob is you know he's not. He's not impressive in
Speaker 1: terms of the way he presents himself. I don't remember
Speaker 1: if he was wearing his you know, his turtleneck and
Speaker 1: gold chains, but he probably was. Turns out this was
Speaker 1: actually a point of pride for Bob. Everybody had to
Speaker 1: wear a tie in Chicago, every lawyer, I should say,
Speaker 1: every lawyer except me. This super casual look was like
Speaker 1: Bob's dress code. No fancy suit, no tie, just a
Speaker 1: gold chain. This was all part of his branding, bling casual.
Speaker 1: I guess you could call it Gary Shapiro. He didn't
Speaker 1: know what to make of this. He's kind of shambling
Speaker 1: and he doesn't speak like a lawyer. You'd never think
Speaker 1: Bob Cooley was an attorney, and that's kind of way
Speaker 1: he present he himself. He was just this guy who
Speaker 1: came into my office completely unimpressive, and sat down and
Speaker 1: started telling me about the root of all evil, which
Speaker 1: was gambling. Illegal gambling. That's what Bob had come in
Speaker 1: to talk about initially, anyhow, and he seemed to know
Speaker 1: an awful lot about how it all worked, how the
Speaker 1: lion's share of the mob's profits came from illegal gambling,
Speaker 1: and this money funded all kinds of illegal activity, including
Speaker 1: public corruption. And look, we're not talking about a petty
Speaker 1: bribe here and there. Back in the nineteen eighties, Chicago
Speaker 1: was one of the most corrupt cities in America. Gary
Speaker 1: was a mob specialist, so he knew a lot of
Speaker 1: this already. He mainly just sat and listened and Bob
Speaker 1: he went on to explain that he himself was a
Speaker 1: big gambler and he was really good at it, but
Speaker 1: he'd seen what happened to the guys who lost, how
Speaker 1: those guys basically became slaves to the mob. You had
Speaker 1: certain paper would have a gambling debt, Judges, politicians, others
Speaker 1: who would gamble and lose a lot of money, and
Speaker 1: they were in fear of being killed or being beaten
Speaker 1: or whatever by the mob. And that's how the mob
Speaker 1: would wind up recruiting a lot of people. That's what
Speaker 1: I was talking to him about. Bob would tell Gary
Speaker 1: that he knew the mob intimately, that he was connected
Speaker 1: to corrupt elected officials, judges, and Alderman, even a state senator.
Speaker 1: Bob claimed to be at the center of all this
Speaker 1: and he was tired of it that he wanted to
Speaker 1: clean up the whole system. Now here's the really weird part.
Speaker 1: Bob was offering his services, but he didn't ask for
Speaker 1: anything in return. In fact, he says he made just
Speaker 1: one request. Bob wanted to confirm that he himself was
Speaker 1: not currently under investigation. Why, Bob claimed it was to
Speaker 1: protect his own reputation so he'd be credible if he
Speaker 1: became a witness for the FEDS. I would never cooperate
Speaker 1: or burn somebody taking help myself. I never would do that.
Speaker 1: I detested stool pigeons and people that you would sell
Speaker 1: out their friends and whatever to help themselves. I would
Speaker 1: never have done that. Bob says he didn't want anyone
Speaker 1: to say years from now that he was out to
Speaker 1: save his own skin. Gary, meanwhile, wasn't sure about what
Speaker 1: had just landed in his lap. He was a prosecutor.
Speaker 1: When he worked with informants, it was always after the
Speaker 1: cops or the FBI had vetted them. That was the
Speaker 1: proper order of things. For some reason, Bob had come
Speaker 1: directly to Gary. Why wasn't so clear, But there had
Speaker 1: to be a reason, right. The meeting ended as it began,
Speaker 1: rather mysteriously. Gary basically said, we'll be back in touch,
Speaker 1: and then Bob stood up and walked out the door.
Speaker 1: So there was Gary in his short sleeves Saturday, kind
Speaker 1: of wondering what the hell just happened. It was intriguing,
Speaker 1: for sure, but something seemed fishing. From my perspective, Bob
Speaker 1: was too good to be true. And so all of
Speaker 1: your antennae are out and you're worried about you know,
Speaker 1: why have the gods delivered this gift to me? There's
Speaker 1: got to be something wrong with this. I had profound
Speaker 1: questions about his motivation, and I get it. I felt
Speaker 1: the exact same way when Bob told me this story,
Speaker 1: And from Gary's perspective, there were a few things about
Speaker 1: this whole encounter that were more than a little puzzling. Obviously,
Speaker 1: Bob knew the dangers of talking to the FEDS, so
Speaker 1: why would Bob take the risk? I mean, he didn't
Speaker 1: seem to be on the run from the mob, and
Speaker 1: he didn't seem to be in trouble with the law either.
Speaker 1: So was Bob for real? I thought the more realistic
Speaker 1: possibility that this was another job who had a Messiah clomplex.
Speaker 1: And yet, I mean, I'm not going to turn down
Speaker 1: the Messiah. I'm not going to say no to the Messiah.
Speaker 1: Bob walked out of Gary's office under the streets of
Speaker 1: downtown Chicago and began to take stock of the situation.
Speaker 1: Once I made the step, I could not undo that.
Speaker 1: And you know, as I said, in an hour, after
Speaker 1: a minute, probably after I started talking to Gary, I
Speaker 1: regretted doing what I did. I regretted coming in there.
Speaker 1: I was mad at myself again, and you know again,
Speaker 1: couldn't understand why I did it. You know, I just couldn't.
Speaker 1: He felt like he'd thrown it all away. Everything he'd
Speaker 1: worked for. Bob had started off as a cop walking
Speaker 1: the beat, scraped his way through law school, slowly built
Speaker 1: up a successful practice as a criminal defense lawyer. He
Speaker 1: was known throughout the city no tie, gold chain Bob.
Speaker 1: He drove around in a big Chrysler that looked a
Speaker 1: bit like a Limo. For a few years, he owned
Speaker 1: a health club and was also part owner of an
Speaker 1: Italian restaurant called Greco's. He'd worked hard to gain the
Speaker 1: confidence of many powerful men, from respected judges to mob captains,
Speaker 1: so why risk all of that now? Suddenly it seemed
Speaker 1: rash crazy. Even Bob began to hope that maybe Gary
Speaker 1: Shapiro would see it this way too. I'm hoping this
Speaker 1: guy thought I was some kind of a nut and
Speaker 1: I wasn't going to call him. I was not going
Speaker 1: to call him or talk to him, or stop in
Speaker 1: to see him. And I'm hoping that nobody comes, you know,
Speaker 1: nobody comes to see me. And I'm even thinking, initially, well,
Speaker 1: if somebody comes, I'm gonna tell him. I changed my mind.
Speaker 1: Bob just hoped that Gary didn't talk to anyone with
Speaker 1: loose lips. The trick now was acting normal, just go
Speaker 1: about with my life and hoping that I wouldn't suddenly
Speaker 1: have somebody come up and shoot me in the back
Speaker 1: of the head. The one person who may have picked
Speaker 1: up on Bob's jitters was Judy d'angelus, Bob's secretary slash
Speaker 1: paralegal slash office manager. She was in her twenties, young
Speaker 1: and wide eyed. Judy she knew Bob about as well
Speaker 1: as anyone did. We were friends. I mean, I was
Speaker 1: never a girlfriend of his. I think I was the
Speaker 1: only secretary to say. And he'll admit that. Judy and
Speaker 1: Bob had a kind of instant synergy. Bob says that
Speaker 1: he trusted her from the moment he first met her.
Speaker 1: I met Judy when she was in a grocery store,
Speaker 1: just in talking to her like a very sharp girl.
Speaker 1: So I suggested, you would you want to come to
Speaker 1: work for me? And you know, oh yeah, sure, I'd
Speaker 1: love it. Whatever I mean. She had obviously no experience
Speaker 1: in the legal field, nothing like that, and I put
Speaker 1: her in charge of my whole office. Wait, what made
Speaker 1: you think, Like you met this random woman at a
Speaker 1: grocery store, Like, what makes you what made you think
Speaker 1: that she would be the right to run your whole office?
Speaker 1: I have no idea take, I don't know why, it
Speaker 1: just it just came to me. Judy knew that Bob
Speaker 1: was a big gambler. Bob bet on sports games mainly.
Speaker 1: He used a bunch of different bookies and these guys
Speaker 1: you had to pay or work out some kind of
Speaker 1: arrangement because almost all of them were backed by the mob,
Speaker 1: so you didn't want to get too deep in the hole.
Speaker 1: But for Bob, gambling was a way of life. I
Speaker 1: think he loved the the actual act of gambling and
Speaker 1: you know, getting it right. I think Bob will tell
Speaker 1: you the same thing that he was not motivated by me,
Speaker 1: but boy, if he had it, he spent it, and
Speaker 1: then if he didn't have it, he'd go out and
Speaker 1: find more. This is part of what made Bob such
Speaker 1: an exciting guy to know. He was a whirlwind of activity,
Speaker 1: and sometimes Judy loved getting swept up in it all.
Speaker 1: So did her then boyfriend now husband. They both told
Speaker 1: me Bob treated them like family. He would buy them dinner,
Speaker 1: take them out for nights on the town, get their
Speaker 1: parking tickets fixed. Bob was like their mobbed up fairy godfather,
Speaker 1: sprinkling magic dust wherever they went. But there were other
Speaker 1: moments when they caught glimpses of Bob's darker dealings. They
Speaker 1: didn't ask too many questions, but they understood the lurking
Speaker 1: dangers and this particular week, even though Judy didn't know
Speaker 1: all the details of what was going on with Bob,
Speaker 1: she knew enough to worry. I was spiritful for Bob's life.
Speaker 1: I would come into the office in the morning, and
Speaker 1: if he didn't call me right away, I didn't know
Speaker 1: if he was in a trunk somewhere dead. And I
Speaker 1: was careful about his gambling. I used to spend hours
Speaker 1: and hours checking different things, checking odds, checking numbers, checking
Speaker 1: power ratings, checking all these things. I didn't do it
Speaker 1: that week. That week, he means, the week he visited Gary,
Speaker 1: the week his life started to unravel. That week, he says,
Speaker 1: he dispensed with his usual precautions, gambled recklessly, placed several
Speaker 1: impulsive bets, and ultimately lost man. I had three or
Speaker 1: four of the worst days of my life gambling. Everything
Speaker 1: I'm doing is wrong. I'm losing I'm losing this, I'm
Speaker 1: losing that. And by now later in the week, I
Speaker 1: realized I go like one hundred and it was like
Speaker 1: one hundred ten, one hundred and twenty thousand dollars. You
Speaker 1: you kind of lost your cool a little bit, Oh,
Speaker 1: no question about it. Bob's concerns about his debts were
Speaker 1: compounded by his gnawing feeling that he hadn't seen the
Speaker 1: last of Gary Shapiro, that by walking into Gary's office,
Speaker 1: he'd put something much bigger into motion, thinking what did
Speaker 1: I do? You know? What did I do? And again
Speaker 1: I was hoping against hope that okay, that'll be the
Speaker 1: end of it. But I knew that wasn't going to
Speaker 1: be the case. I mean, I knew I'd be getting
Speaker 1: a visit. I didn't know when, but I knew I'd
Speaker 1: be getting a visit. Then one morning it happened. I
Speaker 1: walked into the office and that Judy was behind the desks,
Speaker 1: and Judy said to me, I think there's some FBI
Speaker 1: agents here to see you. In the moment she said
Speaker 1: that I knew exactly what it was. It was the
Speaker 1: thing he'd been dreading, the very thing he himself had
Speaker 1: set in motion coming right back at him for FBI
Speaker 1: agents on his doorstep, and they had questions. One of
Speaker 1: the FBI agents to visit Bob that day was Marie Dyson.
Speaker 1: Marie was in some ways an unlikely agent. She joined
Speaker 1: the bureau kind of on a whim after her dad
Speaker 1: suggested that she apply, and that began the process. And
Speaker 1: then I went to Quantico like everybody else for four
Speaker 1: months training, had no idea what I was getting myself into.
Speaker 1: Marie didn't want to mess this up. She was a
Speaker 1: young woman, a real rarity in the bureau. Around the
Speaker 1: time that she joined, only two percent of FBI agents
Speaker 1: were women, and Marie she felt that, Wow, you've entered
Speaker 1: a man's world. You know, we can make mistakes, we
Speaker 1: can screw up. Everybody laughs about it, but y'all don't
Speaker 1: have that luxury. You know you cannot make a mistake.
Speaker 1: And I will speak personally for myself, but I think
Speaker 1: I kind of felt like, well, we need to prove
Speaker 1: ourselves that we can do the job. She was sent
Speaker 1: to Chicago in nineteen eighty one, where she was assigned
Speaker 1: to the public Corruption squad, and she quickly learned the
Speaker 1: mob playbook. The evidence is going to get tainted or
Speaker 1: thrown away. Any eyewitnesses will take care of them, you know,
Speaker 1: they'll be eradicated, and then the judge will be taken
Speaker 1: care of. And it was a way of life, It's
Speaker 1: how it operated. The mob was teflon. So Marie shows
Speaker 1: up at Bob's office with three other agents, all of
Speaker 1: them guys. We walked in and set in Bob's office,
Speaker 1: and he was not very happy about this. And he
Speaker 1: looked around and he said, you all look like FBI
Speaker 1: agents except for the girl. And he always said that
Speaker 1: he would say that, you know, thereafter, because I don't
Speaker 1: know what an FBI agent female was supposed to look like.
Speaker 1: But he didn't think I look like one, which seemed
Speaker 1: to relieve him a little bit. Marie and these other
Speaker 1: agents had managed to piece together some limited info on
Speaker 1: who Bob was. They knew, for example, that he wasn't
Speaker 1: the target of any ongoing investigations, so he was in
Speaker 1: no imminent legal trouble, which raised the question why had
Speaker 1: Bob come in? It was not commonplace. It was very suspicious.
Speaker 1: That's how we looked at it in the beginning. Marie's colleague,
Speaker 1: Steve Bowen, shared her skepticism. He was there that day too.
Speaker 1: Marie and Steve were pretty close. They actually drove to
Speaker 1: work together. Yeah, they were carpool buddies. Steve was a
Speaker 1: former cop from Indianapolis who had entered the FBI at
Speaker 1: thirty five, which was the cutoff for joining, and that
Speaker 1: must have made him just about the oldest rookie in
Speaker 1: the bureau. So in a way, Steven streetwise, but in
Speaker 1: other important ways he was very green. I've only been
Speaker 1: an agent two years. I've got no Chicago Mob background.
Speaker 1: I don't know who the players are. They dropped names
Speaker 1: that would mean absolutely netting to me. He might have
Speaker 1: been green, but he knew enough to realize just how
Speaker 1: rare it was to have a guy like Bob Cooley
Speaker 1: show up and offer to help. Started kidding me unheard of.
Speaker 1: It just doesn't happen for someone just to walk in
Speaker 1: out of the blue. Why is he doing this? I mean,
Speaker 1: he's literally putting his life on the line, and I honestly,
Speaker 1: I think it caught everybody with their pants down. We
Speaker 1: didn't know how to handle it at first, and that's
Speaker 1: really why Steve and Marie visited Bob that day to
Speaker 1: get a handle on things. You've got an attorney that
Speaker 1: we really wan't familiar with. We didn't know how high
Speaker 1: up in the mob he was, if he was at all,
Speaker 1: So we just had to start setting up meetings with
Speaker 1: him and talk to him and trying to get a
Speaker 1: feel for what he's doing, where is coming from, what's
Speaker 1: wrong with him? If anything? Is he a plan? Is
Speaker 1: he a double age. What is he? You couldn't really
Speaker 1: figure out a guy like Bob and just one sitting
Speaker 1: or even three for that matter. So this was actually
Speaker 1: the first of many meetings that Steve and Marie had
Speaker 1: with Bob. They had to vet him, much the way
Speaker 1: the CIA would have to vet a Soviet defector who
Speaker 1: just walked in off the street. And Bob he understood
Speaker 1: this Steve and those others for a long time after
Speaker 1: I came in, I knew they didn't believe me, and
Speaker 1: I knew that they were waiting. You know, they felt
Speaker 1: there something wrong. But you know what was I to say?
Speaker 1: I mean, I knew that just based on certain reactions
Speaker 1: from them, and the best of it. After that first
Speaker 1: meeting at Bob's office, they met elsewhere at a hotel
Speaker 1: where no one would see what they were up to,
Speaker 1: and gradually, over a series of meetings, Bob started talking,
Speaker 1: and once he did, he didn't stop. Bob could give
Speaker 1: us judges, lawyers, police officers, court personnel, politicians, He could
Speaker 1: give us those people. It was like, after having all
Speaker 1: those jitters, he just leaped into the deep end, no
Speaker 1: looking back. He started laying out the details of his
Speaker 1: story that he was a powerbroker for the city's notorious
Speaker 1: First Ward. Technically, the First Ward was just one of
Speaker 1: Chicago's fifty legislative districts, but it was one of the
Speaker 1: most powerful and rumored to be among the most corrupt.
Speaker 1: A political machine run by gangsters, and Bob claimed to
Speaker 1: be their lawyer, their fixer, a trusted confidant. We controlled
Speaker 1: the courts, We controlled the States Attorneys Office, We control
Speaker 1: the police Department. We controlled that absolutely everything. Okay, so
Speaker 1: he's bragging a bit. They didn't control absolutely everything, but
Speaker 1: they controlled an awful lot. Bob was and still is
Speaker 1: a natural storyteller, and he presented himself as the good guy,
Speaker 1: the hero who'd fallen in with the wrong crowd and
Speaker 1: now wanted to make amends. He had a whole mythology
Speaker 1: about himself. Most of it was to put himself in
Speaker 1: a good light and to protect himself. He was street savvy.
Speaker 1: He was a survivor. You understood that. I mean, you
Speaker 1: just can't be a real straight up on his guy
Speaker 1: and survived with this. Bob knew how to keep himself alive,
Speaker 1: and he could excuse me bullshit with the best. It
Speaker 1: all came down to the old bullshit meter. I asked
Speaker 1: Steve Bowen about this, Did you have a gut feeling
Speaker 1: about him? No, and that's what was disturbing. I didn't
Speaker 1: see your tone is all this and you want nothing
Speaker 1: for it. You're not really looking for anything. You're looking
Speaker 1: for money. We tried to get a figure out. I mean,
Speaker 1: what do you want? What are you doing? He says,
Speaker 1: I'm just tired of it. I'm just I don't know
Speaker 1: what happened to change his mind to bring him forward,
Speaker 1: and to this day, I still don't. Bob did want
Speaker 1: one thing. He made one request. I had asked the agents,
Speaker 1: I'm asking you to do me one favor. What's that
Speaker 1: If I get killed, you let everybody know. I wasn't
Speaker 1: doing it because out of fear of the mob or
Speaker 1: or as basically as a stool pigeon. I had come
Speaker 1: forward and I was doing the right thing to clean
Speaker 1: up the system. I asked a couple of the agents that, oh,
Speaker 1: certainly I was. I was scared stiff, but I had
Speaker 1: a mission. Was this was my mission. I've spent the
Speaker 1: last year digging deep into Bob's story, talking to people
Speaker 1: who knew him back in the day, which was a
Speaker 1: whole cast of characters. Because Bob rubbed shoulders with just
Speaker 1: about everybody. Judges, politicians, bookies, gangsters, cops, and hitmen. They
Speaker 1: all confided in him. Bob was a keeper of their secrets.
Speaker 1: Secrets had implicated not just a few powerful men, but
Speaker 1: a whole shadowy realm, a black market of corruption where
Speaker 1: politicians were bought and justice was sold, where for the
Speaker 1: right price, even murderers could walk free. Bob was privy
Speaker 1: to all of it, and he kept it under wraps
Speaker 1: until the spring of nineteen eighty six, when he started
Speaker 1: to talk up on season two of Deep Cover. For
Speaker 1: approximately five years, a Chicago lawyer has been a government informant,
Speaker 1: secretly recording conversations with some of this city's movers and shakers.
Speaker 1: The identity of this informant will come as a shock
Speaker 1: to some powerful people. I can say with all certainty,
Speaker 1: I think he's a hero because he didn't have to
Speaker 1: do what he did, and he did it anyway. Well,
Speaker 1: I can see how people would think that, Yeah, because
Speaker 1: Cooley is very manipulate too. But he just sort of
Speaker 1: got away with murder and he said, don't ever tell
Speaker 1: us what to do. He said, nobody wears a wire
Speaker 1: in US and lives to talk about it. Deep Cover
Speaker 1: is produced by Jacob Smith and Amy Gaines and edited
Speaker 1: by Karen Shakerji. Our senior editor is Jan Guera. Original
Speaker 1: music in our theme was composed by Louis Gara and
Speaker 1: Fawn Williams as our engineer. Our art this season was
Speaker 1: drawn by Cheryl Cook and designed by Sean Carney Mia
Speaker 1: Lobell as our executive producer. Special thanks to Heather Fame,
Speaker 1: John Schnars, Carl Mcliori, Maya Caning, Christina Sullivan, Eric Sandler,
Speaker 1: Mary Beth Smith, Brant Haynes, Maggie Taylor, Nicole Morano, Megan Larson,
Speaker 1: Royston Baserve, Lucy Sullivan, Edith Russlo, Riley Sullivan, Jason Gambrell,
Speaker 1: Martin Gonzalez, and Jacob Weissberg. I'm Jake Halbern. Pleasure Us.
Speaker 1: If you want to learn more about Bob Cooley's story,
Speaker 1: you can check out his memoir, published in two thousand
Speaker 1: and four. It's called When Corruption Was King. Bob co
Speaker 1: wrote it with Hill l Levin. Subscribe to pushkin Plus
Speaker 1: and you can binge the rest of the season right now.
Speaker 1: Adds free. Find pushkin Plus on the deep Cover Show
Speaker 1: page in Apple Podcasts or at pushkin dot fm. To
Speaker 1: find more Pushkin podcasts, listen on the iHeartRadio app, Apple Podcasts,
Speaker 1: or wherever you listen to podcasts.