Speaker 1: Pushkin previously on Deep Cover.
Speaker 2: Bob Cooley fled Chicago in November of nineteen eighty nine.
Speaker 2: Bob's life as he knew it was over. He had
Speaker 2: rejected the witness protection program and instead opted to improvise.
Speaker 2: He took on a new identity and planned to hide
Speaker 2: out Meanwhile, back in Chicago, Bob's efforts resulted in charges
Speaker 2: against at least two dozen men, lawyers, judges, cops, and politicians.
Speaker 2: Chief among them was Pat Marcy, who effectively ran the
Speaker 2: first ward, the Mob's political stronghold.
Speaker 3: So this is like a not just a cascade, it's
Speaker 3: an earthquake on Chicago politics. This is a staggering revelation
Speaker 3: involving a lawyer. Virtually no one outside of a circle
Speaker 3: of real insiders knew at all.
Speaker 2: Bob's days as a covert operative may have been over,
Speaker 2: but he still had work to do. He would be
Speaker 2: the prosecution's star witness in a series of trials. This
Speaker 2: was the final stage of Operation Gambad, the goal break
Speaker 2: the chokehold the Mob had on Chicago. There's a little
Speaker 2: story Bob told me that kind of sums up what
Speaker 2: his life was like after he fled Chicago and It's
Speaker 2: about of all things furniture.
Speaker 4: I started off I first, when I first left town.
Speaker 4: I started off with all my own furniture and all
Speaker 4: the rest of it.
Speaker 2: And all the rest of it, you know, like a
Speaker 2: toaster and a can opener and a TV. Not just that. Initially,
Speaker 2: Bob built a little nest for himself. After bouncing around
Speaker 2: from east to west, he settled down in Richmond, Virginia
Speaker 2: and started getting all domestic.
Speaker 4: I had met a girl who had moved in with me.
Speaker 4: She thought maybe we'd get married, but that wasn't my idea.
Speaker 4: But she had just moved in with me about a
Speaker 4: week before, and I went to Chicago for a trial.
Speaker 2: That was the rhythm of Bob's life. Now, hide out,
Speaker 2: keep a low profile, and then every so often, hop
Speaker 2: on a plane back to the Chicago area, show up
Speaker 2: in court, take the witness stand, and then poof vanish again.
Speaker 2: All told, Bob would end up testifying in nine trials. Anyway,
Speaker 2: After one of his court appearances, Bob is ready to
Speaker 2: head home back to Richmond, where his girlfriend is waiting
Speaker 2: for him. But first Bob needs to stop by an
Speaker 2: FBI office just to check in.
Speaker 4: They had six agents standing there with machine guns and
Speaker 4: with vests on, and they told me to put a
Speaker 4: vest on. And they said, you can't go back home.
Speaker 4: And I said why. They said, supposedly somebody was on
Speaker 4: the way out there to kill me.
Speaker 2: Bob tries to digest all of this. I mean, things
Speaker 2: were going pretty well for him back in Richmond, but
Speaker 2: apparently it was time to move again.
Speaker 4: I said, well, I've got some stuff i'd like to get,
Speaker 4: you know, back home, at my house. And so the
Speaker 4: next day I flew into Richmond. A couple of agents
Speaker 4: met me there. We went to the house and my
Speaker 4: girlfriend I forgot her name now, wasn't home. She was
Speaker 4: at work, and I just packed up a bunch of
Speaker 4: stuff and left her a note. You know, I got
Speaker 4: to leave. Something came up. I'm not coming back. You know,
Speaker 4: everything here is yours.
Speaker 2: And that was that the end of one of Bob
Speaker 2: Cooley's many lives. So he started over in North Carolina,
Speaker 2: where he stayed until there was another scare and he
Speaker 2: had to flee again. It had been twenty years since
Speaker 2: Bob first got involved with the Mob. Ever since then,
Speaker 2: he had been haunted by his relationship with its political czar,
Speaker 2: Pat Marcy and one of its hit men, Harry Elmann.
Speaker 2: Now they would both be prosecuted. This was the reckoning,
Speaker 2: the moment when Bob would have to stare them down
Speaker 2: in court, tell the world what they'd done, and explain
Speaker 2: his own role in it all. This would happen in
Speaker 2: two separate trials that took place in the nineteen nineties.
Speaker 2: These trials would in many ways to find the success
Speaker 2: or failure of Bob's mission, and through it all, Bob's
Speaker 2: main challenge was to stay alive so he could finish
Speaker 2: what he started. I'm Jay Colburn and this is Deep
Speaker 2: Cover mob Land, our final episode the witness. Before Pat
Speaker 2: Marcy was indicted, prosecutors invited him to their off for
Speaker 2: a little visit. Tom Durkin was there for that meeting.
Speaker 2: Today he's a federal judge, but at the time he
Speaker 2: was an assistant US attorney.
Speaker 5: Pat Marcy came in with his lawyer. The attorney explained
Speaker 5: what the charges would be.
Speaker 2: Marcy was older now, he was in his seventies and
Speaker 2: not in the best of health, and he was in
Speaker 2: hot water. Marcy was about to be charged on multiple counts,
Speaker 2: including racketeering, bribery, and extortion. The prosecutors wanted to see
Speaker 2: if Marcy might cooperate.
Speaker 5: And I distinctly remember Pat Marcy saying good luck to
Speaker 5: you and standing up and walking out.
Speaker 2: In other words, go to hell. So Tom and the
Speaker 2: other prosecutors had to build their case, and they had
Speaker 2: a lot to work with. For starters, they had all
Speaker 2: those secret recordings that Bob had made, which they could
Speaker 2: play for the jury. These would prove that Marcy had
Speaker 2: orchestrated bribes. Sure, sometimes Marcy spoke in code, but that's
Speaker 2: where Bob would come into play. He could get on
Speaker 2: the witness stand and offer context, almost like a translator,
Speaker 2: decoding mob speak. The prosecutors also wanted to prove that
Speaker 2: Marcy had arranged to fix court cases in the more
Speaker 2: distant past before Bob had flipped, like that notorious murder
Speaker 2: case back in the seventies involving the reputed hitman Harry Elaman.
Speaker 2: The Feds wanted to prove that Marcy had schemed to
Speaker 2: fix that case, that he was the one who'd recruited
Speaker 2: Bob Cooley to bribe the judge. But proving this would
Speaker 2: be much harder. Sure, Bob could testify, but there were
Speaker 2: no secret recordings to back him up. So who could
Speaker 2: corroborate Bob's story. The judge on the case, Frank Wilson,
Speaker 2: was now dead. He had taken his own life, and
Speaker 2: that left only one person, Catherine Fleming. If you recall
Speaker 2: in nineteen seventy seven, the year of the Harry Elamann trial,
Speaker 2: she was Bob's secretary and lover, but she knew little
Speaker 2: about his shady dealings.
Speaker 6: I wasn't looking to figure it out because it was
Speaker 6: none of my business.
Speaker 2: But Catherine was with Bob at the restaurant when he
Speaker 2: made the payoff to Judge Wilson. She didn't see the
Speaker 2: actual payoff or even know about it at the time,
Speaker 2: but afterwards the judge had told her, you look like
Speaker 2: a nice girl, stay away from him. Tom Durkin, the prosecutor,
Speaker 2: felt that if he could persuade Catherine to testify, she
Speaker 2: could be the lynchpin. Everything she witnessed indicated that Bob
Speaker 2: was telling the truth. Catherine agreed to cooperate, but her
Speaker 2: family was unhappy, especially her mom.
Speaker 6: Oh, she went nuts. She had a fit, lots of screaming.
Speaker 6: She demanded that I'd not testify, that it had nothing
Speaker 6: to do with me, that Bob was wrong to do this, wrong,
Speaker 6: to involve me. She felt that he was a horrible person.
Speaker 6: She felt that everyone was you me, and the mafia
Speaker 6: would kill me.
Speaker 2: Even so, Catherine felt she had to do something.
Speaker 6: I thought that it's very wrong for judges to get
Speaker 6: paid off so that hitman can continue to murder people,
Speaker 6: and nobody wants to testify because their mothers scream at
Speaker 6: them that you're going to get murdered. And I wanted
Speaker 6: to do the right thing.
Speaker 2: Catherine's testimony would be a huge boost for Tom Dirkin
Speaker 2: and the prosecution, especially because she had no reason to lie.
Speaker 2: She was just a regular civilian, a bystander caught up
Speaker 2: in a tangled scheme of corruption, and by testifying she
Speaker 2: would in effect be taking on the mob. In short,
Speaker 2: she bolstered Bob's credibility big time.
Speaker 5: It was remarkable corroboration from a witness who had no
Speaker 5: motive to lie. I thought that was the best piece
Speaker 5: of corroboration I've ever had in any case I ever prosecuted.
Speaker 2: So that was that the prosecution's case was coming together.
Speaker 2: They had Bob, they had his secret recordings, and they
Speaker 2: had Catherine Fleming, the stalwart secretary who would not be intimidated.
Speaker 2: The trial of Pat Marcy kicked off on December fourteenth,
Speaker 2: nineteen ninety two, almost exactly three years after Bob Cooley
Speaker 2: fled Chicago, and on trial alongside him as co defendant,
Speaker 2: was one of Marcy's associates, the first word Alderman Fred Roady.
Speaker 2: In his opening statement, Marcy's defense lawyer Ed Jensen told
Speaker 2: the jury quote, Robert Cooley is a liar who will
Speaker 2: say or do anything to convict Pat Marcy. He's an
Speaker 2: envious man who has spent his whole life lying and cheating,
Speaker 2: and he has decided to put these talents to work
Speaker 2: for the government. So that was the game plan. Smear
Speaker 2: Bob before he even took the stand. Make Bob Cooley
Speaker 2: look like the rat of all time. Eventually, Bob arrived
Speaker 2: at the courthouse to testify, and for the first time
Speaker 2: in year, he came face to face with Pat Marcy.
Speaker 4: I was brought into the courtroom. I was put up
Speaker 4: in the chair. I'm sitting up there in the witness chair.
Speaker 4: I see Pat over there and he's glaring at.
Speaker 2: Me, Bob says. Marcy's lawyer approached him. The two men
Speaker 2: knew each other brushing shoulders in the city's courts.
Speaker 4: Jensen comes walking up to me while the jury is
Speaker 4: being brought in and he says, how are you doing, Bob?
Speaker 4: You know you look good? Everything okay, I get the
Speaker 4: fuck out of here.
Speaker 2: Bob was a witness for the prosecution, so they got
Speaker 2: him first for the direct questioning. Tom Dirkin, the prosecutor,
Speaker 2: asked Bob to tell his story, the whole saga of
Speaker 2: how he got mixed up with the mob in the
Speaker 2: first place, how he met Pat Marcy, and what Marcy
Speaker 2: asked him to do. Bob was calm and collected, clarifying
Speaker 2: the smallest of details. As a former criminal defense lawyer,
Speaker 2: Bob knew exactactly what he needed to do. Tom says
Speaker 2: Bob's performance as a witness was one of the best
Speaker 2: he ever saw.
Speaker 5: Every question I had was answered directly by him. The
Speaker 5: evidence we were able to play the tapes. We put
Speaker 5: up pictures of the main players as he was talking
Speaker 5: about people.
Speaker 2: All the while Pat Marcy sat there as if none
Speaker 2: of this had anything to do with him.
Speaker 5: You couldn't get any emotion out of him. He wasn't
Speaker 5: grimacing or rolling his eyes or muttering under his breath
Speaker 5: or anything like that. He's very stony faced.
Speaker 2: Bob says he also remembers Marcy's cold, hard gaze.
Speaker 4: Pat Marcy is staring at me. When he's staring at me,
Speaker 4: I give him a wink. I give him a wink
Speaker 4: and a smile, and he starts coughing. He started coughing
Speaker 4: and wheezing, almost uncontrollably.
Speaker 2: As all this is happening. Tom has his back to Marcy,
Speaker 2: so we can't see him, but he remembers hearing coughing
Speaker 2: in the moment. Tom didn't think much of it, but
Speaker 2: turns out it was an omen of what was to come.
Speaker 2: A day or so later, Marcy's lawyers announced that he'd
Speaker 2: had a heart attack.
Speaker 7: Tonight, Pat Marcy is in critical condition in the cardiac
Speaker 7: care unit of West Suburban Hospital in oak Park. Despite
Speaker 7: defense objections that the seventy nine year old Marcy should
Speaker 7: not be tried at all due to poor health.
Speaker 2: The plan was to prosecute Marcy again when his health improved,
Speaker 2: but it never did. The case against Marcy ended in
Speaker 2: a mistrial. A short while later, Marcy died. Now you
Speaker 2: might think that Bob would be devastated by this. I
Speaker 2: mean he risked his own life and spent the last
Speaker 2: three years on the run, all in the hopes of
Speaker 2: nailing this guy and sending him to prison. And now this,
Speaker 2: but that's not the way that Bob saw it. Bob,
Speaker 2: in classic Bob fashion, credit for Marcy's death. Wait, are
Speaker 2: you saying that you think you caused him the heart attack?
Speaker 4: I have no doubt in my mind. I have no
Speaker 4: doubt in my mind. But I was gonna say, because
Speaker 4: this man had so much hatred towards me in this system.
Speaker 2: The truth is, there's no real proof that Marcy had
Speaker 2: a heart attack right there in the courtroom while Bob
Speaker 2: was winking at him. But as Bob tells it in
Speaker 2: his mythology, that's how it all played out. In other words,
Speaker 2: he won, though arguably Marcy lived by his own rules
Speaker 2: to the right bold age of seventy nine and checked
Speaker 2: out just in time. I asked Tom, the prosecutor, if
Speaker 2: he felt that Marcy had basically escaped justice.
Speaker 5: He didn't escape justice. He was indicted. He was held
Speaker 5: up to the public as a person who had fixed
Speaker 5: murder cases. He was on trial in a courtroom in
Speaker 5: front of a jury. A lot of the secrets of
Speaker 5: his life were exposed. So he didn't escape justice. Did
Speaker 5: he escape going to jail, sure, but at what price
Speaker 5: he died?
Speaker 2: Pat Marcy's death was a mortal blow to the First Ward.
Speaker 2: Marcy was more than just the boss in so many ways.
Speaker 2: He was the first Ward. He'd been there for decades,
Speaker 2: and his connections, his know how, and the fear that
Speaker 2: he conjured it all died with him. No one could
Speaker 2: really fill his shoes, and the other possible candidates, well,
Speaker 2: they went down with him. Fred Roady was convicted on
Speaker 2: multiple counts of racketeering and extortion. He was sentenced to
Speaker 2: four years in prison. As for John Diarco Junior, the
Speaker 2: poet and state senator, his case also went to trial.
Speaker 2: He was convicted of extortion and sentenced to three years
Speaker 2: in prison. In the years since Marcie's death, the political
Speaker 2: boundaries of Chicago's war Words have been redrawn and then
Speaker 2: redrawn again, and the old First Ward, in both shape
Speaker 2: and power, is no more. Bob may rightly claim credit
Speaker 2: for the downfall of the First Ward, but his most
Speaker 2: defining moment would come in another trial where he would
Speaker 2: face off with the hit man Harry Alaman and try
Speaker 2: to atone for his own original sin. More on that
Speaker 2: after the break, after the trial of Pat Marcy and
Speaker 2: Fred Roady, much of Bob's story became public, and one
Speaker 2: of the biggest revelations was this Bob had bribed a
Speaker 2: judge and helped Harry Alamann, the hit man, go freely.
Speaker 2: That but Catherine Fleming, Bob's secretary, had provided some corroboration,
Speaker 2: And this, among other things, raised the question would prosecutors
Speaker 2: go after Harry again some twenty years later. Mind you,
Speaker 2: doing this wouldn't be easy. Harry had a very powerful
Speaker 2: ally on his side. And I don't mean the mob.
Speaker 2: I'm talking about the Fifth Amendment of the US Constitution.
Speaker 2: It said that no one could be placed in double jeopardy,
Speaker 2: meaning you can't be prosecuted for the same crime twice.
Speaker 2: But turns out state prosecutors came up with a clever workaround.
Speaker 2: They argued that because the original trial appeared to have
Speaker 2: been fixed, well, then Harry had never really been in
Speaker 2: jeopardy in the first place. Hattie. This question was actually
Speaker 2: appealed all the way up to the US Supreme Court.
Speaker 2: In the end, the decision was Harry could be retried.
Speaker 8: Now.
Speaker 2: To give you a quick refresher. The first trial of
Speaker 2: Harry Alamann occurred back in nineteen seventy six. There were
Speaker 2: two eyewitnesses, both of whom identified Harry as the killer.
Speaker 2: The public and Chicago media were shocked by the not
Speaker 2: guilty verdict, but no one was more deeply impacted than
Speaker 2: the family of the victim, Billy Logan. Billy's niece, Johanna
Speaker 2: Santanello says her relatives were haunted for years by what
Speaker 2: had happened.
Speaker 9: They have nothing but this memory of how they last
Speaker 9: seen their family member laying on a street full of
Speaker 9: bull of the hole's moaning.
Speaker 2: They wondered how exactly that trial had ended in an acquittal,
Speaker 2: and they held on to the hope that somehow justice
Speaker 2: still might be served. And then finally, in nineteen ninety seven,
Speaker 2: two decades later, Harry was put back on trial, thanks
Speaker 2: in part to Bob Cooley and the fact that he
Speaker 2: would testify. But the whole thing left Johannah feeling worried.
Speaker 9: Because I just felt, what if he walks again, you know,
Speaker 9: how would my family handle that or could they handle
Speaker 9: any more of this?
Speaker 2: In many ways, this retrial was a culmination, a moment
Speaker 2: of truth not just for the Logan family or even
Speaker 2: for Operation Gambat, but for everyone in Chicago who'd witnessed
Speaker 2: untold decades of judicial corruption. The credibility of the judicial
Speaker 2: system itself seemed to be on the line, because in
Speaker 2: the end, laws and judges and courthouses don't mean a
Speaker 2: damn thing if no one has faith in them. As
Speaker 2: the trial got underway, the prosecution called its witnesses to
Speaker 2: the stand, many of the same people who testified twenty
Speaker 2: years earlier. It was a bit like the reunion of
Speaker 2: an old TV show, with the same actors and a
Speaker 2: few new twists. There was the neighbor who said he'd
Speaker 2: witnessed the murder, the accomplice who said he'd helped Harry
Speaker 2: plan the whole thing. And there were new witnesses too,
Speaker 2: including Bob Cooley. Bob says he showed up with his
Speaker 2: own security detail.
Speaker 4: Well, I guess it was like the mayor or the
Speaker 4: rising coming in. They were so worried about my security
Speaker 4: because of obviously this was going to be a case
Speaker 4: that would be making history.
Speaker 10: It's a very big deal.
Speaker 2: Investigative reporter Carol Marine covered the trial. She also remembers
Speaker 2: all the fanfare surrounding Bob.
Speaker 10: They're surrounded by agents. They're in bulletproof vests. They're guarding you.
Speaker 3: They've got automatic weapons everywhere.
Speaker 10: Yes, you are the center of the universe.
Speaker 2: When he finally took the stand, Bob told the courtroom
Speaker 2: how in the past he'd been a fixer for Pat
Speaker 2: Marcy and the first ward he was in effect a
Speaker 2: tool of the outfit who'd been asked to protect when
Speaker 2: of their most valuable assets, Harry the hook Alaman. Bob
Speaker 2: explained how in the original trial he'd bribed the judge,
Speaker 2: Frank Wilson, and how later after the not guilty verdict
Speaker 2: came out, the judge had told him, you destroyed me.
Speaker 2: Carol was there in the courtroom for this moment.
Speaker 3: You know, Bob Cooley does not demonstrate much emotion at all.
Speaker 3: He's got a pretty flat affect. But there was a
Speaker 3: point in his testimony talking about really almost forcing Frank
Speaker 3: Wilson to take the money in a men's bathroom. I mean,
Speaker 3: he choked with emotion and had to kind of swallow
Speaker 3: hard and.
Speaker 10: Keep talking.
Speaker 3: Because he knew that he was one of the instruments
Speaker 3: of Frank Wilson's demise. He couldn't have been other. Yes,
Speaker 3: the outfit ruined Frank Wilson. Yes, Frank Wilson ruined Frank Wilson,
Speaker 3: But ultimately all of the players in the surround sound
Speaker 3: of that were responsible for the death of Frank Wilson.
Speaker 2: Afterwards, Harry's lawyer had a chance to cross examine Bob.
Speaker 2: His strategy from the start was to discredit him, to
Speaker 2: dredge up Bob's checkered past. He asked Bob if during
Speaker 2: his days as a cop he'd ever been paid off. Yes,
Speaker 2: said Bob, He'd taken so called street money that typically
Speaker 2: meant tips or payoffs from businesses, you know, like bars
Speaker 2: that want to cozy up with the cops. The defense
Speaker 2: lawyer kept hammering away at Bob, portraying him as a
Speaker 2: shifty and shadowy character. In response, Bob was remarkably candid.
Speaker 2: He didn't make elaborate arguments or justifications. He just kind
Speaker 2: of took it on the chin. At one point, he said, quote,
Speaker 2: I'm not making any excuses for what I did. I
Speaker 2: did what I did, but it was an easy way
Speaker 2: to get to the top during that time, and I
Speaker 2: took the easy route.
Speaker 4: This guy is trying to make me out to be
Speaker 4: somebody who's you know, who's a crooked cough passing out bribes.
Speaker 11: Because I guess what he's trying to do is the
Speaker 11: classic I'm going to turnish your reputation and credibility. But
Speaker 11: the whole purpose of you appearing today as as a
Speaker 11: guy who fixes cases in places bribes.
Speaker 4: It's given me credibility in that sense.
Speaker 2: The whole process was tricky for Bob. He wanted to
Speaker 2: be seen as the guy who'd cleaned up Chicago, but
Speaker 2: in order to do that, he had to admit publicly
Speaker 2: to all the most questionable and unsavory things that he'd
Speaker 2: ever done. The danger was that these admissions would define
Speaker 2: who Bob really was because everyone was trying to make
Speaker 2: up their minds about Bob. In his closing statement, the
Speaker 2: prosecutor told the jury quote, I'm telling you you have
Speaker 2: to like Bob Cooley. You don't have to like him,
Speaker 2: but you know what. Bob Cooley faced what he was.
Speaker 2: As the jury finished its deliberations, onlookers packed into the
Speaker 2: gallery to hear the verdict. Johanna Santanello was there with
Speaker 2: the other members of a Logan family, hoping that maybe
Speaker 2: finally there'd be justice for Billy. The jurors came into
Speaker 2: the courtroom and then the verdict was announced for the.
Speaker 9: Murder of William Logan guilty, and it was like, oh
Speaker 9: my god, it's happening. All these years they waited my
Speaker 9: aunt and my uncle and my mom to hear that guilty,
Speaker 9: and it was finally like a burden was lifted off
Speaker 9: of them. Of course, their brother could never be replaced,
Speaker 9: no matter, you know, but to see him actually have
Speaker 9: to pay for what he did meant the world to them.
Speaker 2: So, according to the Chicago Tribune, when the verdict was announced,
Speaker 2: Harry Alamann didn't flinch. He simply blinked his eyes and
Speaker 2: stared straight ahead. Harry was eventually sentenced to one hundred
Speaker 2: to three hundred years in prison. He died behind bars
Speaker 2: after the trial. As reporters clamored for quotes and comments,
Speaker 2: one prosecutor proclaimed, quote, this will close the books on
Speaker 2: an ugly era in Cook County. It's a great day
Speaker 2: for American justice. The one person who was conspicuously absent
Speaker 2: at that moment was Bob Cooley. After testifying, Bob flew
Speaker 2: off to another undisclosed destination, vanishing once again even so
Speaker 2: Bob's presence loomed large in the courtroom that day. After all,
Speaker 2: he was the man who'd both started and finished this saga,
Speaker 2: the fixer who bribed the judge in the first trial
Speaker 2: and then exposed his own trickery at the second trial.
Speaker 2: He was a rat or a hero, depending on who
Speaker 2: you asked. But one thing was clear. Bob's work in
Speaker 2: Chicago is now done. He hadn't expected to survive this process,
Speaker 2: but he had. In fact, he was just fifty five
Speaker 2: years old. So now what what kind of life could
Speaker 2: he really expect? And had it all been worth it?
Speaker 12: Caam driving down a desert highway here? And so you
Speaker 12: got to make him turn left, turn.
Speaker 4: In a mile. Well is.
Speaker 2: Dusty and bleak out here. After almost a year of
Speaker 2: talking to Bob on the phone, I went to see
Speaker 2: him in the obscure little corner of the world where
Speaker 2: he now lives.
Speaker 8: You got to make a left up here. Oh, oh, yeah, somewhere.
Speaker 8: I think I'm about to miss out here. It is here,
Speaker 8: It is okay, Wow, it's.
Speaker 12: Easy to miss.
Speaker 2: Bob lives in a modest house at the edge of
Speaker 2: the desert.
Speaker 4: Here.
Speaker 2: He has a small bedroom which he calls his cubby hole.
Speaker 2: His bedroom floor is stacked with cylinders of pringles and
Speaker 2: jugs of V eight vegetable juice that Bob buys in
Speaker 2: bulk to save money. The place looks like what it is,
Speaker 2: a hideout.
Speaker 11: Hi are you Rosie?
Speaker 2: Bob has a roommate, a woman named Rosie. When I visited,
Speaker 2: she was wearing a house dress with brightly colored, psychedelic
Speaker 2: looking flowers. She's actually the one who owns this house.
Speaker 2: Bob told me that he's lived with her on and
Speaker 2: off for roughly a decade.
Speaker 4: She said, I'm pretty much of a recluse. She said,
Speaker 4: I keep to myself or whatever. And I said, you know, well,
Speaker 4: I think i'd like to move in. She had no
Speaker 4: idea who I was.
Speaker 2: Rosie told me that she knew the broad strokes of
Speaker 2: Bob's life, but never asked about the details.
Speaker 13: We don't talk.
Speaker 2: Wait, how come you never talk your roommate.
Speaker 13: He lives his life. I live my life minus with
Speaker 13: the dogs back there, and his is in here, so
Speaker 13: that's it. He comes in the kitchen. I'm not in
Speaker 13: the kitchen. He does all the cooking. I don't do
Speaker 13: any cooking.
Speaker 11: But aren't you curious?
Speaker 2: Like he used to work for the MOB as a lawyer.
Speaker 12: Does that make you want to know more?
Speaker 10: No?
Speaker 13: No, no, I don't.
Speaker 10: That's me.
Speaker 13: No, I don't need to know.
Speaker 2: So in some ways, Rosie is the perfect housemate for Bob.
Speaker 2: She doesn't pry, though I should point out they did,
Speaker 2: in fact talk. They argued more or less constantly during
Speaker 2: the time that I was there, not small things like
Speaker 2: whether the living room needed dusting or how the pillows
Speaker 2: were situated on the couch. Rosie told me that Bob
Speaker 2: had messed them up.
Speaker 4: I'm kind of embarrassed, though I hope he doesn't take
Speaker 4: a picture of that.
Speaker 13: Kidding, you're embarrassed, Give me a break.
Speaker 12: You guys are a regular odd couple. I gotta tell.
Speaker 13: You we are we if we would be married, I
Speaker 13: polly killed him by now.
Speaker 4: Just to get the insurance right.
Speaker 10: Absolutely.
Speaker 2: Eventually, I suggested that Bob and I get out of
Speaker 2: the house get some space. So we hopped in my
Speaker 2: rental car, and as we drove we chatted. He told
Speaker 2: me how lonely he was in the years after he
Speaker 2: first left Chicago.
Speaker 4: As I'm driving around, I'm so jealous of people. Look,
Speaker 4: I say, somebody with somebody in the car with them,
Speaker 4: and I'm jealous. I mean, it's really hard to explain this.
Speaker 14: I'm curious, like, here you are, You're in this town,
Speaker 14: you're at this roommate live with you for eight years
Speaker 14: and knows nothing about you've got. You said, you've got
Speaker 14: no friends in this town. I mean, are you good
Speaker 14: with that?
Speaker 2: Are you at peace with that?
Speaker 4: Or are you at the moment at the moment, yes,
Speaker 4: you know no, As I said, what are you gonna?
Speaker 4: What am I gonna do? I can't feel sorry for myself.
Speaker 4: It's such a decision I made, and I suspected it
Speaker 4: would be bad, never as bad as I'd got in
Speaker 4: terms of, you know, fighting off the loneliness for a
Speaker 4: long period of time.
Speaker 2: As we continued driving, Bob pointed out a few of
Speaker 2: the local landmarks, restaurants and the like that he told
Speaker 2: me he was so strapped for cash that he hadn't
Speaker 2: really dined out in years. Bob also showed me the
Speaker 2: office of his lawyer, who recently helped him file for bankruptcy.
Speaker 2: Bob told me that he'd been living off credit cards
Speaker 2: for a while, but then the monthly payments got so
Speaker 2: high that they ate up what little money he made
Speaker 2: from Social Security, so declaring bankruptcy, it had been kind
Speaker 2: of a relief over the past twenty five years. It
Speaker 2: hasn't always been like this for Bob. He says that
Speaker 2: when he initially left Chicago, he had some money in savings,
Speaker 2: but Bob, ever the gambler, had made some risky bets
Speaker 2: on the stock market and lost almost all of it.
Speaker 2: Bob also co wrote a memoir with a journalist, Hillel Levin.
Speaker 2: He made some money off the book, but that was
Speaker 2: back in two thousand and four, and in the years
Speaker 2: since then, he's been kind of scraping by. It's ironic really.
Speaker 2: As a kid, Bob loathed the feeling of being poor.
Speaker 2: Remember he hated that his mother had to comb the
Speaker 2: shelves looking for dented cans so she could ask for
Speaker 2: a discount. This, as much as anything, fueled his ambitions
Speaker 2: to become wealthy, to become no tie gold chain Bob
Speaker 2: a guy who walked around town with thousands of dollars
Speaker 2: in his pockets and now here he was all these
Speaker 2: years later, clipping coupons and buying V eight and pringles
Speaker 2: in bulk to make his money. Last in the Hollywoo version,
Speaker 2: of this story, the Bob character would likely have ended
Speaker 2: up on the beach somewhere, maybe down in the Caymans,
Speaker 2: but that's obviously not how it panned out for him.
Speaker 2: And this got me thinking, what was the ending that
Speaker 2: Bob deserved, you know, given everything that he'd done. I mean,
Speaker 2: it was complicated. Bob was the guy who induced his
Speaker 2: friend into taking a bribe that ruined him, a guy
Speaker 2: who helped a murderer walk free, a guy who prevented
Speaker 2: a female cop who'd been beaten from getting justice. But
Speaker 2: this was also the guy who tried to right these wrongs.
Speaker 2: He'd shown tremendous courage. Bob made a stand against the
Speaker 2: mob and expose systematic corruption, and the impact he had
Speaker 2: in the city of Chicago, it's indisputable. Here's Carol Marine,
Speaker 2: the investigative journalist.
Speaker 3: Bob was one of the most consequential witnesses that ever
Speaker 3: took the stand in a federal organized crime trial or
Speaker 3: probably almost any trial. He did this city and this
Speaker 3: state a great service. He risked his life. He did
Speaker 3: something that no one else had done. He penetrated the
Speaker 3: first Ward and he took down its power brokers. It
Speaker 3: was tremendously important in fighting public corruption.
Speaker 2: Of course, Chicago still has its challenges. In twenty nineteen,
Speaker 2: the city's longest serving aldermen, a guy named Ed Burke,
Speaker 2: was indicted on fourteen counts of racketeering, extortion, and bribery.
Speaker 2: Burke went down because another city alderman betrayed him. That
Speaker 2: guy wore a wire for two years and made a
Speaker 2: series of secret recordings. It was a long con. Seemed
Speaker 2: like he took a page right out of Bob Cooley's playbook.
Speaker 2: Operation Gambat may now seem like ancient history, something that
Speaker 2: happened way back in the eighties, but the ripple effects
Speaker 2: are still being felt to this day. There's this concept
Speaker 2: in the law known as camouflaging bias. The idea is
Speaker 2: a judge takes a bribe in one case and then
Speaker 2: to avoid suspicion, punishes the hell out of other defendants
Speaker 2: so it looks like the judge is tough on crime.
Speaker 2: Then years later the defendant cries foul, says, hey, that
Speaker 2: wasn't fair. I got hit with this huge sentence because
Speaker 2: this corrupt judge was covering his tracks. And that's what's
Speaker 2: happening in Chicago right now. Prisoners arguing that they too
Speaker 2: were victims of the corruption that Bob exposed, And so
Speaker 2: the story goes on. Some members of Bob's family really
Speaker 2: appreciate what he did for the city of Chicago. His
Speaker 2: brother Joe, who was an assistant US attorney, told me
Speaker 2: that he was proud of Bob's legacy, and his brother
Speaker 2: Dennis told me he gradually came to respect what Bob
Speaker 2: had done. But it's been trickier with some of Bob's
Speaker 2: other siblings.
Speaker 4: I mean, and I have a sister and another brother
Speaker 4: who want nothing to do with me. They want absolutely
Speaker 4: nothing to do with me. Why do you think that
Speaker 4: is because they believe what they saw that I'm some
Speaker 4: kind of a rat. I mean, why else would it be.
Speaker 2: I spoke with both of the siblings Bob's referring to here,
Speaker 2: Tim and Diane. Both of them conveyed to me in
Speaker 2: so many words that they cared about Bob, but they'd
Speaker 2: never really been close with him. That even as a kid,
Speaker 2: Bob had been unscrupulous, hot headed, and full of himself.
Speaker 2: I talked about this at length with Tim Cooley. If
Speaker 2: you recall, Tim is the yoga instructor who lives in Vermont.
Speaker 15: I don't know.
Speaker 10: You know, why is Bob Bob?
Speaker 15: You know I I've been thinking about it and and
Speaker 15: this may sound weird, but I don't know if Bob
Speaker 15: has ever felt loved. I've never known a loving relationship
Speaker 15: that he's been in. Actually, you know, he's had a
Speaker 15: lot of sex, I'm sure, but I don't think he's
Speaker 15: ever been in love. He's never had a relationship that
Speaker 15: I've ever been aware of, And so it's like he's
Speaker 15: looking for he's looking to fill that lack in some
Speaker 15: other ways.
Speaker 2: Tim offered me a take on his brother that was
Speaker 2: neither rat nor hero, but something else altogether.
Speaker 10: I'm afraid that.
Speaker 15: That what matters most of all is just that he's known,
Speaker 15: that he's known, and the goodness is almost irrelevant. I'm
Speaker 15: sorry to say. The most important thing is that, look,
Speaker 15: I am a big man. Look I am somebody. I
Speaker 15: can do really horrible things, I can do good things.
Speaker 15: I'm somebody.
Speaker 2: When I relayed all of this back to Bob, word
Speaker 2: for word, to my great surprise, Bob shrugged his shoulders
Speaker 2: and said he's right in a sense. In the year
Speaker 2: that I spent talking with Bob, he was always upbeat
Speaker 2: and quick to laugh. Part of this is just Bob's nature,
Speaker 2: but I think he was also kind of selling me
Speaker 2: on his story, as if to say, look at me,
Speaker 2: I live quite a life, didn't I? And he had.
Speaker 2: But when I visited Bob in person and saw his
Speaker 2: cubby hole and the roommate who didn't really know him
Speaker 2: or cared to know him, I got a different feeling entirely.
Speaker 2: Bob's bravada was gone, and in its place was an
Speaker 2: air of defeat and almost disbelief, as if he couldn't
Speaker 2: quite fathom that this is how things had turned out.
Speaker 2: I asked Bob if there was any part of him
Speaker 2: that regretted what he'd done, if he could go back
Speaker 2: in time, would he have done it differently? Not flipped
Speaker 2: at all?
Speaker 4: Absolutely, I mean absolutely. The day I put on that
Speaker 4: wire it was all over. I knew it was all over.
Speaker 4: I knew that, you know, my life could never be,
Speaker 4: But I never dreamed it would be as bad as God.
Speaker 4: I'm no better rop than some of those beggars out
Speaker 4: there in the street, and I'd better not even think
Speaker 4: about it, because again, it is the way it is.
Speaker 4: So I mean to say, I wish I could have
Speaker 4: changed that are you kidding me.
Speaker 12: I mean, I'm trying to understand how you think about
Speaker 12: your own life. If the defining thing in your life
Speaker 12: is the thing you wish you hadn't done.
Speaker 4: You've seen my life now. Think about that. You've seen
Speaker 4: my life now, and you can't understand how I wished
Speaker 4: I hadn't done that. That makes no sense.
Speaker 12: Well, I understand it. It's not that I don't understand it.
Speaker 4: I just.
Speaker 12: Trying to wrap my head around it, that's all.
Speaker 4: But you know, again, I don't know. I'm just saying that.
Speaker 4: There's no question in my mind. I'd be an idiot
Speaker 4: to say, gee, I'm glad that I, you know, destroyed myself,
Speaker 4: and that's what I wound up doing. I destroyed. Bob
Speaker 4: Cooley is no longer. This is not Bob Cooley name
Speaker 4: wise or even otherwise. What do you mean they left?
Speaker 4: Bob Cooley was that person back there in Chicago that
Speaker 4: everybody came to when they had trouble and was able
Speaker 4: to help all kinds of people and be able to
Speaker 4: do whatever he damned pleased, never worried about getting arrested
Speaker 4: or getting parking tickets or anything whatever I wanted.
Speaker 12: What is Bob Cooley.
Speaker 4: Now just just to you know, somebody waiting to die.
Speaker 4: That pretty much sums it all up right now at
Speaker 4: this stage. I mean, they you kidding me? What is it?
Speaker 4: He's nobody, he's nothing.
Speaker 2: Hearing him talk like this, I had to wonder once
Speaker 2: again why Bob had flipped in the first place. What
Speaker 2: had he been hoping for. There were so many different theories,
Speaker 2: and Bob himself kind of waffled on this question, offering
Speaker 2: different explanations on different days. It was to clean up
Speaker 2: the city, it was to heed the advice of his
Speaker 2: dying father. He was to stand up to Pat Marcy,
Speaker 2: who was a bully. And it's true Bob did not
Speaker 2: like being pushed around. But my feeling about all of
Speaker 2: these was yeah, maybe, but they seemed like partial explanations
Speaker 2: at best. The theory I heard the most was that
Speaker 2: Bob owed to the mob. That's what was in all
Speaker 2: the papers at the time. But I don't really buy it.
Speaker 2: I mean, think about the timeline. Bob flipped back in
Speaker 2: nineteen eighty six, he fled town in nineteen eighty nine.
Speaker 2: So put yourself in Bob's shoes if you were truly
Speaker 2: worried about owing money to the mob, and you were
Speaker 2: spooped that some goons were going to break your legs
Speaker 2: were worse, Why would you flip and then stick around
Speaker 2: town for the next three and a half years. You wouldn't.
Speaker 2: It's true Bob was a gambler, and I think that
Speaker 2: this does in fact explain what he did. I kept
Speaker 2: thinking back to what Bob told me on the very
Speaker 2: first day that we talked, that he'd been walking down
Speaker 2: the street to get a Deli sandwich, he'd seen the
Speaker 2: Prosecutor's office and just walked in on an impulse. And
Speaker 2: now I could see it. Here's Bob the gambler, because
Speaker 2: walking into that office was, in some ways the biggest
Speaker 2: gamble of all. He was wagering his life. He was
Speaker 2: betting that he could almost magically save himself and perhaps
Speaker 2: the city of Chicago while he was at it. Not
Speaker 2: a sensible bet, a real long shot, you might say,
Speaker 2: which is probably exactly why he did it. One day,
Speaker 2: toward the end of my visit with Bob, we had
Speaker 2: lunch together at the little place where I was staying.
Speaker 2: I ordered her some pizza, which we didn't finish, and
Speaker 2: I was about to throw the leftover slices out when
Speaker 2: Bob stopped me, no save those. He told me he
Speaker 2: wanted to feed the wildlife.
Speaker 12: Why do you like to do it?
Speaker 4: Because I've been doing it all my life pretty much.
Speaker 4: I like to feed the animals.
Speaker 10: Why.
Speaker 4: I'll be rewarded down the road for it.
Speaker 12: It's always something for something.
Speaker 4: I like you. I like animals. You know, I feel
Speaker 4: bad when I see him out there. You know they
Speaker 4: might be going hungry. It's always been my nature. I
Speaker 4: just do it.
Speaker 2: We took the scraps of pizza and drove over to
Speaker 2: one of Bob's favorite spots. It was at the edge
Speaker 2: of a parking lot next to a strip mall. He
Speaker 2: came here often. This is kind of a random spot.
Speaker 5: Why do you pick this spot?
Speaker 4: We're like, we're at a over You'll see them all
Speaker 4: over here over on the other side. There, they've got
Speaker 4: a fast food restaurant, two fast food restaurants, and that's
Speaker 4: where the birds seem to migrate.
Speaker 2: I stood there and watched as the birds flocked around him,
Speaker 2: swirling and chirping. For a moment, he seemed genuinely content.
Speaker 2: The whole scene reminded me of how back when he
Speaker 2: was still in Chicago, wearing a wire. He used to
Speaker 2: feed the baby raccoons with no ulterior motives, just a
Speaker 2: pure and simple act, a real rarity, because nothing in
Speaker 2: Bob's life was ever simple.
Speaker 12: Your herds are up there at the corner, looks like yeah.
Speaker 4: No, they for some reason, they always fly away and
Speaker 4: then they come back. But you'll get them cross the
Speaker 4: way over here and they'll come back and get it.
Speaker 4: The braver ones get fed the most. There's some of
Speaker 4: them coming up above.
Speaker 2: Deep Cover is produced by Jacob Smith and Amy Gaines
Speaker 2: and edited by Karen Chakerji. Our senior editor is Jen Guera.
Speaker 2: Original music and the deep Cover theme was composed by
Speaker 2: Luis Garra, with performances by Luise Audrian Terrasas, Alan Fajardo,
Speaker 2: Mi Longoria, and Jimmy Messer. Flawn Williams is our engineer.
Speaker 2: Our art this season was drawn by Cheryl Cook and
Speaker 2: designed by Sean Carney. Mia Lobel is our executive producer.
Speaker 2: Special thanks to Heather Fain, John Schnarz, Carly Migliori, Maya Caning,
Speaker 2: Christina Sullivan, Eric Sandler, Mary Beth Smith, Brant Haynes, Maggie Taylor,
Speaker 2: Nicole Morano, Megan Larson, Morgan Ratner, Royston Deserve, Lucy Sullivan,
Speaker 2: Edith Russello, Riley Sullivan, Jen Sanchez, Jason Gambrell, Martin Gonzalez,
Speaker 2: and Jacob Weisberg. Additional special thanks to Jill Gillette, Travis Dunlap,
Speaker 2: Maggie de Poy, Bill Hogan, David Grossman, Mike Shephard, Jim Wagner,
Speaker 2: Denny Cherrillo, Lisa Chase Patterson, and Michael Deutsch. Also Christian McNally,
Speaker 2: Isabel Vasquez, Jesse de Bartolomeo, Jane Miliotis, Sarah Kraditch, and
Speaker 2: the National Archives at CHU Chicago. I'm Jake Halbert. If
Speaker 2: you like this season of deep Cover, then you should
Speaker 2: really check out our first season, The Drug Wars, which
Speaker 2: tells the story of an FBI agent who goes under
Speaker 2: cover with a biker gang and uncovers a series of
Speaker 2: clues that leads to a war, I mean, a full
Speaker 2: scale invasion. Also check out Pushkin's other true crime podcasts,
Speaker 2: Lost Hills and Bad Women. These shows and more are
Speaker 2: available ad free for Pushkin Plus subscribers. To find more
Speaker 2: Pushkin podcasts, listen on the iHeartRadio app, Apple Podcasts, or
Speaker 2: wherever you listen to podcasts,