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Speaker 1: Pushkin previously on Deep Cover.

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Speaker 2: Bob Cooley fled Chicago in November of nineteen eighty nine.

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Speaker 2: Bob's life as he knew it was over. He had

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Speaker 2: rejected the witness protection program and instead opted to improvise.

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Speaker 2: He took on a new identity and planned to hide

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Speaker 2: out Meanwhile, back in Chicago, Bob's efforts resulted in charges

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Speaker 2: against at least two dozen men, lawyers, judges, cops, and politicians.

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Speaker 2: Chief among them was Pat Marcy, who effectively ran the

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Speaker 2: first ward, the Mob's political stronghold.

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Speaker 3: So this is like a not just a cascade, it's

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Speaker 3: an earthquake on Chicago politics. This is a staggering revelation

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Speaker 3: involving a lawyer. Virtually no one outside of a circle

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Speaker 3: of real insiders knew at all.

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Speaker 2: Bob's days as a covert operative may have been over,

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Speaker 2: but he still had work to do. He would be

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Speaker 2: the prosecution's star witness in a series of trials. This

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Speaker 2: was the final stage of Operation Gambad, the goal break

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Speaker 2: the chokehold the Mob had on Chicago. There's a little

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Speaker 2: story Bob told me that kind of sums up what

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Speaker 2: his life was like after he fled Chicago and It's

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Speaker 2: about of all things furniture.

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Speaker 4: I started off I first, when I first left town.

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Speaker 4: I started off with all my own furniture and all

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Speaker 4: the rest of it.

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Speaker 2: And all the rest of it, you know, like a

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Speaker 2: toaster and a can opener and a TV. Not just that. Initially,

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Speaker 2: Bob built a little nest for himself. After bouncing around

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Speaker 2: from east to west, he settled down in Richmond, Virginia

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Speaker 2: and started getting all domestic.

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Speaker 4: I had met a girl who had moved in with me.

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Speaker 4: She thought maybe we'd get married, but that wasn't my idea.

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Speaker 4: But she had just moved in with me about a

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Speaker 4: week before, and I went to Chicago for a trial.

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Speaker 2: That was the rhythm of Bob's life. Now, hide out,

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Speaker 2: keep a low profile, and then every so often, hop

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Speaker 2: on a plane back to the Chicago area, show up

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Speaker 2: in court, take the witness stand, and then poof vanish again.

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Speaker 2: All told, Bob would end up testifying in nine trials. Anyway,

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Speaker 2: After one of his court appearances, Bob is ready to

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Speaker 2: head home back to Richmond, where his girlfriend is waiting

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Speaker 2: for him. But first Bob needs to stop by an

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Speaker 2: FBI office just to check in.

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Speaker 4: They had six agents standing there with machine guns and

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Speaker 4: with vests on, and they told me to put a

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Speaker 4: vest on. And they said, you can't go back home.

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Speaker 4: And I said why. They said, supposedly somebody was on

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Speaker 4: the way out there to kill me.

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Speaker 2: Bob tries to digest all of this. I mean, things

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Speaker 2: were going pretty well for him back in Richmond, but

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Speaker 2: apparently it was time to move again.

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Speaker 4: I said, well, I've got some stuff i'd like to get,

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Speaker 4: you know, back home, at my house. And so the

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Speaker 4: next day I flew into Richmond. A couple of agents

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Speaker 4: met me there. We went to the house and my

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Speaker 4: girlfriend I forgot her name now, wasn't home. She was

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Speaker 4: at work, and I just packed up a bunch of

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Speaker 4: stuff and left her a note. You know, I got

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Speaker 4: to leave. Something came up. I'm not coming back. You know,

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Speaker 4: everything here is yours.

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Speaker 2: And that was that the end of one of Bob

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Speaker 2: Cooley's many lives. So he started over in North Carolina,

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Speaker 2: where he stayed until there was another scare and he

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Speaker 2: had to flee again. It had been twenty years since

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Speaker 2: Bob first got involved with the Mob. Ever since then,

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Speaker 2: he had been haunted by his relationship with its political czar,

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Speaker 2: Pat Marcy and one of its hit men, Harry Elmann.

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Speaker 2: Now they would both be prosecuted. This was the reckoning,

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Speaker 2: the moment when Bob would have to stare them down

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Speaker 2: in court, tell the world what they'd done, and explain

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Speaker 2: his own role in it all. This would happen in

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Speaker 2: two separate trials that took place in the nineteen nineties.

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Speaker 2: These trials would in many ways to find the success

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Speaker 2: or failure of Bob's mission, and through it all, Bob's

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Speaker 2: main challenge was to stay alive so he could finish

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Speaker 2: what he started. I'm Jay Colburn and this is Deep

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Speaker 2: Cover mob Land, our final episode the witness. Before Pat

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Speaker 2: Marcy was indicted, prosecutors invited him to their off for

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Speaker 2: a little visit. Tom Durkin was there for that meeting.

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Speaker 2: Today he's a federal judge, but at the time he

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Speaker 2: was an assistant US attorney.

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Speaker 5: Pat Marcy came in with his lawyer. The attorney explained

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Speaker 5: what the charges would be.

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Speaker 2: Marcy was older now, he was in his seventies and

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Speaker 2: not in the best of health, and he was in

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Speaker 2: hot water. Marcy was about to be charged on multiple counts,

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Speaker 2: including racketeering, bribery, and extortion. The prosecutors wanted to see

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Speaker 2: if Marcy might cooperate.

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Speaker 5: And I distinctly remember Pat Marcy saying good luck to

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Speaker 5: you and standing up and walking out.

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Speaker 2: In other words, go to hell. So Tom and the

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Speaker 2: other prosecutors had to build their case, and they had

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Speaker 2: a lot to work with. For starters, they had all

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Speaker 2: those secret recordings that Bob had made, which they could

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Speaker 2: play for the jury. These would prove that Marcy had

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Speaker 2: orchestrated bribes. Sure, sometimes Marcy spoke in code, but that's

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Speaker 2: where Bob would come into play. He could get on

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Speaker 2: the witness stand and offer context, almost like a translator,

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Speaker 2: decoding mob speak. The prosecutors also wanted to prove that

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Speaker 2: Marcy had arranged to fix court cases in the more

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Speaker 2: distant past before Bob had flipped, like that notorious murder

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Speaker 2: case back in the seventies involving the reputed hitman Harry Elaman.

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Speaker 2: The Feds wanted to prove that Marcy had schemed to

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Speaker 2: fix that case, that he was the one who'd recruited

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Speaker 2: Bob Cooley to bribe the judge. But proving this would

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Speaker 2: be much harder. Sure, Bob could testify, but there were

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Speaker 2: no secret recordings to back him up. So who could

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Speaker 2: corroborate Bob's story. The judge on the case, Frank Wilson,

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Speaker 2: was now dead. He had taken his own life, and

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Speaker 2: that left only one person, Catherine Fleming. If you recall

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Speaker 2: in nineteen seventy seven, the year of the Harry Elamann trial,

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Speaker 2: she was Bob's secretary and lover, but she knew little

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Speaker 2: about his shady dealings.

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Speaker 6: I wasn't looking to figure it out because it was

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Speaker 6: none of my business.

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Speaker 2: But Catherine was with Bob at the restaurant when he

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Speaker 2: made the payoff to Judge Wilson. She didn't see the

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Speaker 2: actual payoff or even know about it at the time,

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Speaker 2: but afterwards the judge had told her, you look like

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Speaker 2: a nice girl, stay away from him. Tom Durkin, the prosecutor,

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Speaker 2: felt that if he could persuade Catherine to testify, she

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Speaker 2: could be the lynchpin. Everything she witnessed indicated that Bob

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Speaker 2: was telling the truth. Catherine agreed to cooperate, but her

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Speaker 2: family was unhappy, especially her mom.

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Speaker 6: Oh, she went nuts. She had a fit, lots of screaming.

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Speaker 6: She demanded that I'd not testify, that it had nothing

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Speaker 6: to do with me, that Bob was wrong to do this, wrong,

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Speaker 6: to involve me. She felt that he was a horrible person.

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Speaker 6: She felt that everyone was you me, and the mafia

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Speaker 6: would kill me.

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Speaker 2: Even so, Catherine felt she had to do something.

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Speaker 6: I thought that it's very wrong for judges to get

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Speaker 6: paid off so that hitman can continue to murder people,

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Speaker 6: and nobody wants to testify because their mothers scream at

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Speaker 6: them that you're going to get murdered. And I wanted

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Speaker 6: to do the right thing.

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Speaker 2: Catherine's testimony would be a huge boost for Tom Dirkin

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Speaker 2: and the prosecution, especially because she had no reason to lie.

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Speaker 2: She was just a regular civilian, a bystander caught up

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Speaker 2: in a tangled scheme of corruption, and by testifying she

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Speaker 2: would in effect be taking on the mob. In short,

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Speaker 2: she bolstered Bob's credibility big time.

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Speaker 5: It was remarkable corroboration from a witness who had no

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Speaker 5: motive to lie. I thought that was the best piece

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Speaker 5: of corroboration I've ever had in any case I ever prosecuted.

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Speaker 2: So that was that the prosecution's case was coming together.

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Speaker 2: They had Bob, they had his secret recordings, and they

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Speaker 2: had Catherine Fleming, the stalwart secretary who would not be intimidated.

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Speaker 2: The trial of Pat Marcy kicked off on December fourteenth,

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Speaker 2: nineteen ninety two, almost exactly three years after Bob Cooley

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Speaker 2: fled Chicago, and on trial alongside him as co defendant,

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Speaker 2: was one of Marcy's associates, the first word Alderman Fred Roady.

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Speaker 2: In his opening statement, Marcy's defense lawyer Ed Jensen told

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Speaker 2: the jury quote, Robert Cooley is a liar who will

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Speaker 2: say or do anything to convict Pat Marcy. He's an

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Speaker 2: envious man who has spent his whole life lying and cheating,

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Speaker 2: and he has decided to put these talents to work

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Speaker 2: for the government. So that was the game plan. Smear

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Speaker 2: Bob before he even took the stand. Make Bob Cooley

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Speaker 2: look like the rat of all time. Eventually, Bob arrived

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Speaker 2: at the courthouse to testify, and for the first time

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Speaker 2: in year, he came face to face with Pat Marcy.

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Speaker 4: I was brought into the courtroom. I was put up

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Speaker 4: in the chair. I'm sitting up there in the witness chair.

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Speaker 4: I see Pat over there and he's glaring at.

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Speaker 2: Me, Bob says. Marcy's lawyer approached him. The two men

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Speaker 2: knew each other brushing shoulders in the city's courts.

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Speaker 4: Jensen comes walking up to me while the jury is

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Speaker 4: being brought in and he says, how are you doing, Bob?

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Speaker 4: You know you look good? Everything okay, I get the

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Speaker 4: fuck out of here.

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Speaker 2: Bob was a witness for the prosecution, so they got

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Speaker 2: him first for the direct questioning. Tom Dirkin, the prosecutor,

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Speaker 2: asked Bob to tell his story, the whole saga of

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Speaker 2: how he got mixed up with the mob in the

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Speaker 2: first place, how he met Pat Marcy, and what Marcy

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Speaker 2: asked him to do. Bob was calm and collected, clarifying

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Speaker 2: the smallest of details. As a former criminal defense lawyer,

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Speaker 2: Bob knew exactactly what he needed to do. Tom says

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Speaker 2: Bob's performance as a witness was one of the best

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Speaker 2: he ever saw.

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Speaker 5: Every question I had was answered directly by him. The

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Speaker 5: evidence we were able to play the tapes. We put

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Speaker 5: up pictures of the main players as he was talking

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Speaker 5: about people.

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Speaker 2: All the while Pat Marcy sat there as if none

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Speaker 2: of this had anything to do with him.

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Speaker 5: You couldn't get any emotion out of him. He wasn't

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Speaker 5: grimacing or rolling his eyes or muttering under his breath

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Speaker 5: or anything like that. He's very stony faced.

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Speaker 2: Bob says he also remembers Marcy's cold, hard gaze.

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Speaker 4: Pat Marcy is staring at me. When he's staring at me,

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Speaker 4: I give him a wink. I give him a wink

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Speaker 4: and a smile, and he starts coughing. He started coughing

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Speaker 4: and wheezing, almost uncontrollably.

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Speaker 2: As all this is happening. Tom has his back to Marcy,

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Speaker 2: so we can't see him, but he remembers hearing coughing

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Speaker 2: in the moment. Tom didn't think much of it, but

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Speaker 2: turns out it was an omen of what was to come.

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Speaker 2: A day or so later, Marcy's lawyers announced that he'd

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Speaker 2: had a heart attack.

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Speaker 7: Tonight, Pat Marcy is in critical condition in the cardiac

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Speaker 7: care unit of West Suburban Hospital in oak Park. Despite

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Speaker 7: defense objections that the seventy nine year old Marcy should

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Speaker 7: not be tried at all due to poor health.

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Speaker 2: The plan was to prosecute Marcy again when his health improved,

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Speaker 2: but it never did. The case against Marcy ended in

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Speaker 2: a mistrial. A short while later, Marcy died. Now you

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Speaker 2: might think that Bob would be devastated by this. I

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Speaker 2: mean he risked his own life and spent the last

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Speaker 2: three years on the run, all in the hopes of

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Speaker 2: nailing this guy and sending him to prison. And now this,

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Speaker 2: but that's not the way that Bob saw it. Bob,

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Speaker 2: in classic Bob fashion, credit for Marcy's death. Wait, are

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Speaker 2: you saying that you think you caused him the heart attack?

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Speaker 4: I have no doubt in my mind. I have no

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Speaker 4: doubt in my mind. But I was gonna say, because

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Speaker 4: this man had so much hatred towards me in this system.

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Speaker 2: The truth is, there's no real proof that Marcy had

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Speaker 2: a heart attack right there in the courtroom while Bob

220
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Speaker 2: was winking at him. But as Bob tells it in

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Speaker 2: his mythology, that's how it all played out. In other words,

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Speaker 2: he won, though arguably Marcy lived by his own rules

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Speaker 2: to the right bold age of seventy nine and checked

224
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Speaker 2: out just in time. I asked Tom, the prosecutor, if

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Speaker 2: he felt that Marcy had basically escaped justice.

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Speaker 5: He didn't escape justice. He was indicted. He was held

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Speaker 5: up to the public as a person who had fixed

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Speaker 5: murder cases. He was on trial in a courtroom in

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Speaker 5: front of a jury. A lot of the secrets of

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Speaker 5: his life were exposed. So he didn't escape justice. Did

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Speaker 5: he escape going to jail, sure, but at what price

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Speaker 5: he died?

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Speaker 2: Pat Marcy's death was a mortal blow to the First Ward.

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Speaker 2: Marcy was more than just the boss in so many ways.

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Speaker 2: He was the first Ward. He'd been there for decades,

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Speaker 2: and his connections, his know how, and the fear that

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Speaker 2: he conjured it all died with him. No one could

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Speaker 2: really fill his shoes, and the other possible candidates, well,

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Speaker 2: they went down with him. Fred Roady was convicted on

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Speaker 2: multiple counts of racketeering and extortion. He was sentenced to

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Speaker 2: four years in prison. As for John Diarco Junior, the

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Speaker 2: poet and state senator, his case also went to trial.

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Speaker 2: He was convicted of extortion and sentenced to three years

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Speaker 2: in prison. In the years since Marcie's death, the political

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Speaker 2: boundaries of Chicago's war Words have been redrawn and then

246
00:16:11,436 --> 00:16:15,996
Speaker 2: redrawn again, and the old First Ward, in both shape

247
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Speaker 2: and power, is no more. Bob may rightly claim credit

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Speaker 2: for the downfall of the First Ward, but his most

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Speaker 2: defining moment would come in another trial where he would

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Speaker 2: face off with the hit man Harry Alaman and try

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Speaker 2: to atone for his own original sin. More on that

252
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Speaker 2: after the break, after the trial of Pat Marcy and

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Speaker 2: Fred Roady, much of Bob's story became public, and one

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Speaker 2: of the biggest revelations was this Bob had bribed a

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Speaker 2: judge and helped Harry Alamann, the hit man, go freely.

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Speaker 2: That but Catherine Fleming, Bob's secretary, had provided some corroboration,

257
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Speaker 2: And this, among other things, raised the question would prosecutors

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Speaker 2: go after Harry again some twenty years later. Mind you,

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Speaker 2: doing this wouldn't be easy. Harry had a very powerful

260
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Speaker 2: ally on his side. And I don't mean the mob.

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Speaker 2: I'm talking about the Fifth Amendment of the US Constitution.

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Speaker 2: It said that no one could be placed in double jeopardy,

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Speaker 2: meaning you can't be prosecuted for the same crime twice.

264
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Speaker 2: But turns out state prosecutors came up with a clever workaround.

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Speaker 2: They argued that because the original trial appeared to have

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Speaker 2: been fixed, well, then Harry had never really been in

267
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Speaker 2: jeopardy in the first place. Hattie. This question was actually

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Speaker 2: appealed all the way up to the US Supreme Court.

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Speaker 2: In the end, the decision was Harry could be retried.

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Speaker 8: Now.

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Speaker 2: To give you a quick refresher. The first trial of

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00:18:06,236 --> 00:18:10,116
Speaker 2: Harry Alamann occurred back in nineteen seventy six. There were

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Speaker 2: two eyewitnesses, both of whom identified Harry as the killer.

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Speaker 2: The public and Chicago media were shocked by the not

275
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Speaker 2: guilty verdict, but no one was more deeply impacted than

276
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Speaker 2: the family of the victim, Billy Logan. Billy's niece, Johanna

277
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Speaker 2: Santanello says her relatives were haunted for years by what

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Speaker 2: had happened.

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Speaker 9: They have nothing but this memory of how they last

280
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Speaker 9: seen their family member laying on a street full of

281
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Speaker 9: bull of the hole's moaning.

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Speaker 2: They wondered how exactly that trial had ended in an acquittal,

283
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Speaker 2: and they held on to the hope that somehow justice

284
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Speaker 2: still might be served. And then finally, in nineteen ninety seven,

285
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Speaker 2: two decades later, Harry was put back on trial, thanks

286
00:18:59,396 --> 00:19:02,076
Speaker 2: in part to Bob Cooley and the fact that he

287
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Speaker 2: would testify. But the whole thing left Johannah feeling worried.

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Speaker 9: Because I just felt, what if he walks again, you know,

289
00:19:12,676 --> 00:19:15,996
Speaker 9: how would my family handle that or could they handle

290
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Speaker 9: any more of this?

291
00:19:20,396 --> 00:19:24,196
Speaker 2: In many ways, this retrial was a culmination, a moment

292
00:19:24,196 --> 00:19:27,516
Speaker 2: of truth not just for the Logan family or even

293
00:19:27,556 --> 00:19:31,756
Speaker 2: for Operation Gambat, but for everyone in Chicago who'd witnessed

294
00:19:31,876 --> 00:19:37,236
Speaker 2: untold decades of judicial corruption. The credibility of the judicial

295
00:19:37,276 --> 00:19:40,236
Speaker 2: system itself seemed to be on the line, because in

296
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Speaker 2: the end, laws and judges and courthouses don't mean a

297
00:19:44,436 --> 00:19:52,396
Speaker 2: damn thing if no one has faith in them. As

298
00:19:52,396 --> 00:19:55,876
Speaker 2: the trial got underway, the prosecution called its witnesses to

299
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Speaker 2: the stand, many of the same people who testified twenty

300
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Speaker 2: years earlier. It was a bit like the reunion of

301
00:20:01,796 --> 00:20:04,836
Speaker 2: an old TV show, with the same actors and a

302
00:20:04,836 --> 00:20:08,036
Speaker 2: few new twists. There was the neighbor who said he'd

303
00:20:08,076 --> 00:20:11,276
Speaker 2: witnessed the murder, the accomplice who said he'd helped Harry

304
00:20:11,316 --> 00:20:14,156
Speaker 2: plan the whole thing. And there were new witnesses too,

305
00:20:14,596 --> 00:20:18,156
Speaker 2: including Bob Cooley. Bob says he showed up with his

306
00:20:18,196 --> 00:20:19,596
Speaker 2: own security detail.

307
00:20:19,876 --> 00:20:23,036
Speaker 4: Well, I guess it was like the mayor or the

308
00:20:23,276 --> 00:20:26,956
Speaker 4: rising coming in. They were so worried about my security

309
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Speaker 4: because of obviously this was going to be a case

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Speaker 4: that would be making history.

311
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Speaker 10: It's a very big deal.

312
00:20:34,796 --> 00:20:39,396
Speaker 2: Investigative reporter Carol Marine covered the trial. She also remembers

313
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Speaker 2: all the fanfare surrounding Bob.

314
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Speaker 10: They're surrounded by agents. They're in bulletproof vests. They're guarding you.

315
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Speaker 3: They've got automatic weapons everywhere.

316
00:20:51,676 --> 00:20:56,316
Speaker 10: Yes, you are the center of the universe.

317
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Speaker 2: When he finally took the stand, Bob told the courtroom

318
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Speaker 2: how in the past he'd been a fixer for Pat

319
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Speaker 2: Marcy and the first ward he was in effect a

320
00:21:06,556 --> 00:21:09,036
Speaker 2: tool of the outfit who'd been asked to protect when

321
00:21:09,196 --> 00:21:14,116
Speaker 2: of their most valuable assets, Harry the hook Alaman. Bob

322
00:21:14,156 --> 00:21:17,636
Speaker 2: explained how in the original trial he'd bribed the judge,

323
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Speaker 2: Frank Wilson, and how later after the not guilty verdict

324
00:21:21,516 --> 00:21:25,316
Speaker 2: came out, the judge had told him, you destroyed me.

325
00:21:27,596 --> 00:21:29,796
Speaker 2: Carol was there in the courtroom for this moment.

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Speaker 3: You know, Bob Cooley does not demonstrate much emotion at all.

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Speaker 3: He's got a pretty flat affect. But there was a

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Speaker 3: point in his testimony talking about really almost forcing Frank

329
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Speaker 3: Wilson to take the money in a men's bathroom. I mean,

330
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Speaker 3: he choked with emotion and had to kind of swallow

331
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Speaker 3: hard and.

332
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Speaker 10: Keep talking.

333
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Speaker 3: Because he knew that he was one of the instruments

334
00:22:01,356 --> 00:22:06,876
Speaker 3: of Frank Wilson's demise. He couldn't have been other. Yes,

335
00:22:06,996 --> 00:22:12,596
Speaker 3: the outfit ruined Frank Wilson. Yes, Frank Wilson ruined Frank Wilson,

336
00:22:13,316 --> 00:22:17,516
Speaker 3: But ultimately all of the players in the surround sound

337
00:22:17,676 --> 00:22:22,796
Speaker 3: of that were responsible for the death of Frank Wilson.

338
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Speaker 2: Afterwards, Harry's lawyer had a chance to cross examine Bob.

339
00:22:31,716 --> 00:22:35,236
Speaker 2: His strategy from the start was to discredit him, to

340
00:22:35,316 --> 00:22:39,116
Speaker 2: dredge up Bob's checkered past. He asked Bob if during

341
00:22:39,116 --> 00:22:42,876
Speaker 2: his days as a cop he'd ever been paid off. Yes,

342
00:22:42,916 --> 00:22:46,596
Speaker 2: said Bob, He'd taken so called street money that typically

343
00:22:46,676 --> 00:22:50,196
Speaker 2: meant tips or payoffs from businesses, you know, like bars

344
00:22:50,196 --> 00:22:53,116
Speaker 2: that want to cozy up with the cops. The defense

345
00:22:53,196 --> 00:22:56,396
Speaker 2: lawyer kept hammering away at Bob, portraying him as a

346
00:22:56,436 --> 00:23:01,556
Speaker 2: shifty and shadowy character. In response, Bob was remarkably candid.

347
00:23:01,956 --> 00:23:06,316
Speaker 2: He didn't make elaborate arguments or justifications. He just kind

348
00:23:06,316 --> 00:23:09,556
Speaker 2: of took it on the chin. At one point, he said, quote,

349
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Speaker 2: I'm not making any excuses for what I did. I

350
00:23:13,316 --> 00:23:15,316
Speaker 2: did what I did, but it was an easy way

351
00:23:15,316 --> 00:23:17,836
Speaker 2: to get to the top during that time, and I

352
00:23:17,916 --> 00:23:18,876
Speaker 2: took the easy route.

353
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Speaker 4: This guy is trying to make me out to be

354
00:23:21,236 --> 00:23:25,196
Speaker 4: somebody who's you know, who's a crooked cough passing out bribes.

355
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Speaker 11: Because I guess what he's trying to do is the

356
00:23:26,916 --> 00:23:29,676
Speaker 11: classic I'm going to turnish your reputation and credibility. But

357
00:23:29,716 --> 00:23:32,916
Speaker 11: the whole purpose of you appearing today as as a

358
00:23:32,956 --> 00:23:36,156
Speaker 11: guy who fixes cases in places bribes.

359
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Speaker 4: It's given me credibility in that sense.

360
00:23:38,916 --> 00:23:42,476
Speaker 2: The whole process was tricky for Bob. He wanted to

361
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Speaker 2: be seen as the guy who'd cleaned up Chicago, but

362
00:23:46,356 --> 00:23:49,356
Speaker 2: in order to do that, he had to admit publicly

363
00:23:49,436 --> 00:23:52,756
Speaker 2: to all the most questionable and unsavory things that he'd

364
00:23:52,796 --> 00:23:57,356
Speaker 2: ever done. The danger was that these admissions would define

365
00:23:57,436 --> 00:24:01,796
Speaker 2: who Bob really was because everyone was trying to make

366
00:24:01,876 --> 00:24:06,036
Speaker 2: up their minds about Bob. In his closing statement, the

367
00:24:06,036 --> 00:24:10,196
Speaker 2: prosecutor told the jury quote, I'm telling you you have

368
00:24:10,276 --> 00:24:13,036
Speaker 2: to like Bob Cooley. You don't have to like him,

369
00:24:13,196 --> 00:24:16,516
Speaker 2: but you know what. Bob Cooley faced what he was.

370
00:24:19,476 --> 00:24:23,396
Speaker 2: As the jury finished its deliberations, onlookers packed into the

371
00:24:23,436 --> 00:24:27,596
Speaker 2: gallery to hear the verdict. Johanna Santanello was there with

372
00:24:27,636 --> 00:24:31,556
Speaker 2: the other members of a Logan family, hoping that maybe

373
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Speaker 2: finally there'd be justice for Billy. The jurors came into

374
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Speaker 2: the courtroom and then the verdict was announced for the.

375
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Speaker 9: Murder of William Logan guilty, and it was like, oh

376
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Speaker 9: my god, it's happening. All these years they waited my

377
00:24:53,436 --> 00:24:58,876
Speaker 9: aunt and my uncle and my mom to hear that guilty,

378
00:24:59,836 --> 00:25:05,036
Speaker 9: and it was finally like a burden was lifted off

379
00:25:05,036 --> 00:25:10,236
Speaker 9: of them. Of course, their brother could never be replaced,

380
00:25:10,716 --> 00:25:15,716
Speaker 9: no matter, you know, but to see him actually have

381
00:25:15,836 --> 00:25:20,756
Speaker 9: to pay for what he did meant the world to them.

382
00:25:20,796 --> 00:25:35,356
Speaker 2: So, according to the Chicago Tribune, when the verdict was announced,

383
00:25:35,596 --> 00:25:39,756
Speaker 2: Harry Alamann didn't flinch. He simply blinked his eyes and

384
00:25:39,796 --> 00:25:44,356
Speaker 2: stared straight ahead. Harry was eventually sentenced to one hundred

385
00:25:44,356 --> 00:25:51,556
Speaker 2: to three hundred years in prison. He died behind bars

386
00:25:53,356 --> 00:25:57,036
Speaker 2: after the trial. As reporters clamored for quotes and comments,

387
00:25:57,236 --> 00:26:01,716
Speaker 2: one prosecutor proclaimed, quote, this will close the books on

388
00:26:01,756 --> 00:26:04,916
Speaker 2: an ugly era in Cook County. It's a great day

389
00:26:04,996 --> 00:26:17,516
Speaker 2: for American justice. The one person who was conspicuously absent

390
00:26:17,556 --> 00:26:22,276
Speaker 2: at that moment was Bob Cooley. After testifying, Bob flew

391
00:26:22,276 --> 00:26:28,236
Speaker 2: off to another undisclosed destination, vanishing once again even so

392
00:26:28,636 --> 00:26:32,476
Speaker 2: Bob's presence loomed large in the courtroom that day. After all,

393
00:26:32,676 --> 00:26:35,596
Speaker 2: he was the man who'd both started and finished this saga,

394
00:26:36,036 --> 00:26:38,556
Speaker 2: the fixer who bribed the judge in the first trial

395
00:26:38,876 --> 00:26:41,556
Speaker 2: and then exposed his own trickery at the second trial.

396
00:26:42,396 --> 00:26:45,236
Speaker 2: He was a rat or a hero, depending on who

397
00:26:45,276 --> 00:26:50,836
Speaker 2: you asked. But one thing was clear. Bob's work in

398
00:26:50,916 --> 00:26:55,196
Speaker 2: Chicago is now done. He hadn't expected to survive this process,

399
00:26:55,716 --> 00:26:58,516
Speaker 2: but he had. In fact, he was just fifty five

400
00:26:58,636 --> 00:27:02,796
Speaker 2: years old. So now what what kind of life could

401
00:27:02,836 --> 00:27:06,236
Speaker 2: he really expect? And had it all been worth it?

402
00:27:24,916 --> 00:27:30,676
Speaker 12: Caam driving down a desert highway here? And so you

403
00:27:30,756 --> 00:27:33,036
Speaker 12: got to make him turn left, turn.

404
00:27:33,796 --> 00:27:38,996
Speaker 4: In a mile. Well is.

405
00:27:41,116 --> 00:27:46,956
Speaker 2: Dusty and bleak out here. After almost a year of

406
00:27:46,996 --> 00:27:49,636
Speaker 2: talking to Bob on the phone, I went to see

407
00:27:49,716 --> 00:27:52,636
Speaker 2: him in the obscure little corner of the world where

408
00:27:52,676 --> 00:27:53,436
Speaker 2: he now lives.

409
00:27:55,636 --> 00:27:59,796
Speaker 8: You got to make a left up here. Oh, oh, yeah, somewhere.

410
00:27:59,996 --> 00:28:02,156
Speaker 8: I think I'm about to miss out here. It is here,

411
00:28:02,156 --> 00:28:06,996
Speaker 8: It is okay, Wow, it's.

412
00:28:06,876 --> 00:28:07,436
Speaker 12: Easy to miss.

413
00:28:08,916 --> 00:28:11,076
Speaker 2: Bob lives in a modest house at the edge of

414
00:28:11,076 --> 00:28:11,596
Speaker 2: the desert.

415
00:28:12,196 --> 00:28:12,396
Speaker 4: Here.

416
00:28:12,436 --> 00:28:15,196
Speaker 2: He has a small bedroom which he calls his cubby hole.

417
00:28:15,756 --> 00:28:18,836
Speaker 2: His bedroom floor is stacked with cylinders of pringles and

418
00:28:18,956 --> 00:28:21,956
Speaker 2: jugs of V eight vegetable juice that Bob buys in

419
00:28:22,076 --> 00:28:25,636
Speaker 2: bulk to save money. The place looks like what it is,

420
00:28:25,956 --> 00:28:26,556
Speaker 2: a hideout.

421
00:28:27,036 --> 00:28:29,596
Speaker 11: Hi are you Rosie?

422
00:28:31,276 --> 00:28:35,116
Speaker 2: Bob has a roommate, a woman named Rosie. When I visited,

423
00:28:35,316 --> 00:28:38,676
Speaker 2: she was wearing a house dress with brightly colored, psychedelic

424
00:28:38,716 --> 00:28:42,556
Speaker 2: looking flowers. She's actually the one who owns this house.

425
00:28:43,316 --> 00:28:45,756
Speaker 2: Bob told me that he's lived with her on and

426
00:28:45,796 --> 00:28:47,676
Speaker 2: off for roughly a decade.

427
00:28:48,076 --> 00:28:50,436
Speaker 4: She said, I'm pretty much of a recluse. She said,

428
00:28:50,476 --> 00:28:54,196
Speaker 4: I keep to myself or whatever. And I said, you know, well,

429
00:28:54,276 --> 00:28:56,036
Speaker 4: I think i'd like to move in. She had no

430
00:28:56,116 --> 00:28:57,116
Speaker 4: idea who I was.

431
00:28:57,956 --> 00:29:00,476
Speaker 2: Rosie told me that she knew the broad strokes of

432
00:29:00,516 --> 00:29:03,836
Speaker 2: Bob's life, but never asked about the details.

433
00:29:04,436 --> 00:29:05,156
Speaker 13: We don't talk.

434
00:29:06,916 --> 00:29:09,076
Speaker 2: Wait, how come you never talk your roommate.

435
00:29:10,236 --> 00:29:13,916
Speaker 13: He lives his life. I live my life minus with

436
00:29:14,036 --> 00:29:17,356
Speaker 13: the dogs back there, and his is in here, so

437
00:29:18,476 --> 00:29:21,556
Speaker 13: that's it. He comes in the kitchen. I'm not in

438
00:29:21,636 --> 00:29:24,196
Speaker 13: the kitchen. He does all the cooking. I don't do

439
00:29:24,316 --> 00:29:24,996
Speaker 13: any cooking.

440
00:29:25,396 --> 00:29:26,516
Speaker 11: But aren't you curious?

441
00:29:26,556 --> 00:29:29,036
Speaker 2: Like he used to work for the MOB as a lawyer.

442
00:29:29,076 --> 00:29:30,476
Speaker 12: Does that make you want to know more?

443
00:29:30,636 --> 00:29:31,356
Speaker 10: No?

444
00:29:31,356 --> 00:29:34,836
Speaker 13: No, no, I don't.

445
00:29:35,956 --> 00:29:36,356
Speaker 10: That's me.

446
00:29:37,676 --> 00:29:39,756
Speaker 13: No, I don't need to know.

447
00:29:40,796 --> 00:29:44,476
Speaker 2: So in some ways, Rosie is the perfect housemate for Bob.

448
00:29:45,036 --> 00:29:48,436
Speaker 2: She doesn't pry, though I should point out they did,

449
00:29:48,516 --> 00:29:52,116
Speaker 2: in fact talk. They argued more or less constantly during

450
00:29:52,116 --> 00:29:54,796
Speaker 2: the time that I was there, not small things like

451
00:29:54,996 --> 00:29:57,996
Speaker 2: whether the living room needed dusting or how the pillows

452
00:29:57,996 --> 00:30:00,756
Speaker 2: were situated on the couch. Rosie told me that Bob

453
00:30:00,796 --> 00:30:01,596
Speaker 2: had messed them up.

454
00:30:01,996 --> 00:30:04,076
Speaker 4: I'm kind of embarrassed, though I hope he doesn't take

455
00:30:04,076 --> 00:30:04,676
Speaker 4: a picture of that.

456
00:30:05,196 --> 00:30:07,956
Speaker 13: Kidding, you're embarrassed, Give me a break.

457
00:30:11,596 --> 00:30:13,876
Speaker 12: You guys are a regular odd couple. I gotta tell.

458
00:30:13,756 --> 00:30:18,316
Speaker 13: You we are we if we would be married, I

459
00:30:18,396 --> 00:30:19,876
Speaker 13: polly killed him by now.

460
00:30:20,676 --> 00:30:21,956
Speaker 4: Just to get the insurance right.

461
00:30:22,476 --> 00:30:23,316
Speaker 10: Absolutely.

462
00:30:24,156 --> 00:30:26,876
Speaker 2: Eventually, I suggested that Bob and I get out of

463
00:30:26,876 --> 00:30:30,276
Speaker 2: the house get some space. So we hopped in my

464
00:30:30,316 --> 00:30:34,316
Speaker 2: rental car, and as we drove we chatted. He told

465
00:30:34,316 --> 00:30:36,556
Speaker 2: me how lonely he was in the years after he

466
00:30:36,596 --> 00:30:37,636
Speaker 2: first left Chicago.

467
00:30:38,036 --> 00:30:41,716
Speaker 4: As I'm driving around, I'm so jealous of people. Look,

468
00:30:41,836 --> 00:30:43,876
Speaker 4: I say, somebody with somebody in the car with them,

469
00:30:43,876 --> 00:30:46,876
Speaker 4: and I'm jealous. I mean, it's really hard to explain this.

470
00:30:47,516 --> 00:30:50,236
Speaker 14: I'm curious, like, here you are, You're in this town,

471
00:30:50,356 --> 00:30:52,876
Speaker 14: you're at this roommate live with you for eight years

472
00:30:52,916 --> 00:30:54,996
Speaker 14: and knows nothing about you've got. You said, you've got

473
00:30:55,076 --> 00:30:58,076
Speaker 14: no friends in this town. I mean, are you good

474
00:30:58,116 --> 00:30:58,316
Speaker 14: with that?

475
00:30:58,396 --> 00:30:59,276
Speaker 2: Are you at peace with that?

476
00:30:59,436 --> 00:31:01,756
Speaker 4: Or are you at the moment at the moment, yes,

477
00:31:01,916 --> 00:31:05,916
Speaker 4: you know no, As I said, what are you gonna?

478
00:31:05,956 --> 00:31:10,196
Speaker 4: What am I gonna do? I can't feel sorry for myself.

479
00:31:10,196 --> 00:31:14,596
Speaker 4: It's such a decision I made, and I suspected it

480
00:31:14,636 --> 00:31:18,196
Speaker 4: would be bad, never as bad as I'd got in

481
00:31:18,316 --> 00:31:20,756
Speaker 4: terms of, you know, fighting off the loneliness for a

482
00:31:20,756 --> 00:31:21,676
Speaker 4: long period of time.

483
00:31:22,796 --> 00:31:25,436
Speaker 2: As we continued driving, Bob pointed out a few of

484
00:31:25,436 --> 00:31:28,996
Speaker 2: the local landmarks, restaurants and the like that he told

485
00:31:28,996 --> 00:31:31,916
Speaker 2: me he was so strapped for cash that he hadn't

486
00:31:31,916 --> 00:31:35,276
Speaker 2: really dined out in years. Bob also showed me the

487
00:31:35,316 --> 00:31:38,636
Speaker 2: office of his lawyer, who recently helped him file for bankruptcy.

488
00:31:39,316 --> 00:31:41,276
Speaker 2: Bob told me that he'd been living off credit cards

489
00:31:41,276 --> 00:31:44,316
Speaker 2: for a while, but then the monthly payments got so

490
00:31:44,516 --> 00:31:46,796
Speaker 2: high that they ate up what little money he made

491
00:31:46,796 --> 00:31:52,156
Speaker 2: from Social Security, so declaring bankruptcy, it had been kind

492
00:31:52,196 --> 00:31:58,836
Speaker 2: of a relief over the past twenty five years. It

493
00:31:58,876 --> 00:32:01,916
Speaker 2: hasn't always been like this for Bob. He says that

494
00:32:01,956 --> 00:32:05,316
Speaker 2: when he initially left Chicago, he had some money in savings,

495
00:32:05,876 --> 00:32:09,676
Speaker 2: but Bob, ever the gambler, had made some risky bets

496
00:32:09,716 --> 00:32:12,716
Speaker 2: on the stock market and lost almost all of it.

497
00:32:13,716 --> 00:32:16,916
Speaker 2: Bob also co wrote a memoir with a journalist, Hillel Levin.

498
00:32:17,476 --> 00:32:20,476
Speaker 2: He made some money off the book, but that was

499
00:32:20,516 --> 00:32:23,716
Speaker 2: back in two thousand and four, and in the years

500
00:32:23,756 --> 00:32:29,436
Speaker 2: since then, he's been kind of scraping by. It's ironic really.

501
00:32:29,996 --> 00:32:33,196
Speaker 2: As a kid, Bob loathed the feeling of being poor.

502
00:32:33,756 --> 00:32:36,396
Speaker 2: Remember he hated that his mother had to comb the

503
00:32:36,436 --> 00:32:39,476
Speaker 2: shelves looking for dented cans so she could ask for

504
00:32:39,516 --> 00:32:43,916
Speaker 2: a discount. This, as much as anything, fueled his ambitions

505
00:32:43,956 --> 00:32:47,876
Speaker 2: to become wealthy, to become no tie gold chain Bob

506
00:32:48,396 --> 00:32:51,196
Speaker 2: a guy who walked around town with thousands of dollars

507
00:32:51,196 --> 00:32:57,276
Speaker 2: in his pockets and now here he was all these

508
00:32:57,396 --> 00:33:01,956
Speaker 2: years later, clipping coupons and buying V eight and pringles

509
00:33:01,996 --> 00:33:09,676
Speaker 2: in bulk to make his money. Last in the Hollywoo version,

510
00:33:09,716 --> 00:33:13,396
Speaker 2: of this story, the Bob character would likely have ended

511
00:33:13,476 --> 00:33:16,476
Speaker 2: up on the beach somewhere, maybe down in the Caymans,

512
00:33:17,156 --> 00:33:20,356
Speaker 2: but that's obviously not how it panned out for him.

513
00:33:20,796 --> 00:33:23,596
Speaker 2: And this got me thinking, what was the ending that

514
00:33:23,636 --> 00:33:28,436
Speaker 2: Bob deserved, you know, given everything that he'd done. I mean,

515
00:33:28,596 --> 00:33:32,316
Speaker 2: it was complicated. Bob was the guy who induced his

516
00:33:32,516 --> 00:33:36,436
Speaker 2: friend into taking a bribe that ruined him, a guy

517
00:33:36,436 --> 00:33:39,796
Speaker 2: who helped a murderer walk free, a guy who prevented

518
00:33:39,796 --> 00:33:43,876
Speaker 2: a female cop who'd been beaten from getting justice. But

519
00:33:44,516 --> 00:33:47,356
Speaker 2: this was also the guy who tried to right these wrongs.

520
00:33:47,956 --> 00:33:51,756
Speaker 2: He'd shown tremendous courage. Bob made a stand against the

521
00:33:51,796 --> 00:33:55,956
Speaker 2: mob and expose systematic corruption, and the impact he had

522
00:33:55,956 --> 00:34:00,476
Speaker 2: in the city of Chicago, it's indisputable. Here's Carol Marine,

523
00:34:00,556 --> 00:34:01,876
Speaker 2: the investigative journalist.

524
00:34:02,236 --> 00:34:05,676
Speaker 3: Bob was one of the most consequential witnesses that ever

525
00:34:05,756 --> 00:34:10,276
Speaker 3: took the stand in a federal organized crime trial or

526
00:34:10,556 --> 00:34:15,996
Speaker 3: probably almost any trial. He did this city and this

527
00:34:16,156 --> 00:34:21,956
Speaker 3: state a great service. He risked his life. He did

528
00:34:22,036 --> 00:34:26,676
Speaker 3: something that no one else had done. He penetrated the

529
00:34:26,716 --> 00:34:31,676
Speaker 3: first Ward and he took down its power brokers. It

530
00:34:31,756 --> 00:34:35,716
Speaker 3: was tremendously important in fighting public corruption.

531
00:34:36,596 --> 00:34:41,156
Speaker 2: Of course, Chicago still has its challenges. In twenty nineteen,

532
00:34:41,556 --> 00:34:45,396
Speaker 2: the city's longest serving aldermen, a guy named Ed Burke,

533
00:34:45,876 --> 00:34:50,556
Speaker 2: was indicted on fourteen counts of racketeering, extortion, and bribery.

534
00:34:51,516 --> 00:34:55,636
Speaker 2: Burke went down because another city alderman betrayed him. That

535
00:34:55,716 --> 00:34:58,516
Speaker 2: guy wore a wire for two years and made a

536
00:34:58,556 --> 00:35:03,356
Speaker 2: series of secret recordings. It was a long con. Seemed

537
00:35:03,396 --> 00:35:06,756
Speaker 2: like he took a page right out of Bob Cooley's playbook.

538
00:35:10,396 --> 00:35:13,876
Speaker 2: Operation Gambat may now seem like ancient history, something that

539
00:35:13,876 --> 00:35:17,196
Speaker 2: happened way back in the eighties, but the ripple effects

540
00:35:17,196 --> 00:35:20,756
Speaker 2: are still being felt to this day. There's this concept

541
00:35:20,796 --> 00:35:24,756
Speaker 2: in the law known as camouflaging bias. The idea is

542
00:35:24,876 --> 00:35:27,396
Speaker 2: a judge takes a bribe in one case and then

543
00:35:27,556 --> 00:35:30,916
Speaker 2: to avoid suspicion, punishes the hell out of other defendants

544
00:35:31,196 --> 00:35:33,716
Speaker 2: so it looks like the judge is tough on crime.

545
00:35:34,476 --> 00:35:38,036
Speaker 2: Then years later the defendant cries foul, says, hey, that

546
00:35:38,076 --> 00:35:40,996
Speaker 2: wasn't fair. I got hit with this huge sentence because

547
00:35:41,036 --> 00:35:44,996
Speaker 2: this corrupt judge was covering his tracks. And that's what's

548
00:35:45,036 --> 00:35:49,996
Speaker 2: happening in Chicago right now. Prisoners arguing that they too

549
00:35:50,156 --> 00:35:54,076
Speaker 2: were victims of the corruption that Bob exposed, And so

550
00:35:54,636 --> 00:36:02,276
Speaker 2: the story goes on. Some members of Bob's family really

551
00:36:02,356 --> 00:36:05,596
Speaker 2: appreciate what he did for the city of Chicago. His

552
00:36:05,716 --> 00:36:09,036
Speaker 2: brother Joe, who was an assistant US attorney, told me

553
00:36:09,196 --> 00:36:12,156
Speaker 2: that he was proud of Bob's legacy, and his brother

554
00:36:12,236 --> 00:36:15,436
Speaker 2: Dennis told me he gradually came to respect what Bob

555
00:36:15,476 --> 00:36:18,636
Speaker 2: had done. But it's been trickier with some of Bob's

556
00:36:18,676 --> 00:36:19,476
Speaker 2: other siblings.

557
00:36:20,076 --> 00:36:23,316
Speaker 4: I mean, and I have a sister and another brother

558
00:36:24,196 --> 00:36:26,716
Speaker 4: who want nothing to do with me. They want absolutely

559
00:36:26,756 --> 00:36:29,396
Speaker 4: nothing to do with me. Why do you think that

560
00:36:29,516 --> 00:36:32,356
Speaker 4: is because they believe what they saw that I'm some

561
00:36:32,476 --> 00:36:35,236
Speaker 4: kind of a rat. I mean, why else would it be.

562
00:36:35,996 --> 00:36:38,876
Speaker 2: I spoke with both of the siblings Bob's referring to here,

563
00:36:39,316 --> 00:36:42,796
Speaker 2: Tim and Diane. Both of them conveyed to me in

564
00:36:42,916 --> 00:36:46,556
Speaker 2: so many words that they cared about Bob, but they'd

565
00:36:46,596 --> 00:36:49,636
Speaker 2: never really been close with him. That even as a kid,

566
00:36:49,916 --> 00:36:53,356
Speaker 2: Bob had been unscrupulous, hot headed, and full of himself.

567
00:36:54,076 --> 00:36:57,356
Speaker 2: I talked about this at length with Tim Cooley. If

568
00:36:57,356 --> 00:37:00,836
Speaker 2: you recall, Tim is the yoga instructor who lives in Vermont.

569
00:37:01,636 --> 00:37:02,156
Speaker 15: I don't know.

570
00:37:02,516 --> 00:37:03,676
Speaker 10: You know, why is Bob Bob?

571
00:37:03,956 --> 00:37:09,596
Speaker 15: You know I I've been thinking about it and and

572
00:37:09,636 --> 00:37:13,636
Speaker 15: this may sound weird, but I don't know if Bob

573
00:37:13,676 --> 00:37:17,796
Speaker 15: has ever felt loved. I've never known a loving relationship

574
00:37:17,796 --> 00:37:21,756
Speaker 15: that he's been in. Actually, you know, he's had a

575
00:37:21,756 --> 00:37:25,076
Speaker 15: lot of sex, I'm sure, but I don't think he's

576
00:37:25,116 --> 00:37:29,276
Speaker 15: ever been in love. He's never had a relationship that

577
00:37:29,356 --> 00:37:33,156
Speaker 15: I've ever been aware of, And so it's like he's

578
00:37:33,196 --> 00:37:39,076
Speaker 15: looking for he's looking to fill that lack in some

579
00:37:39,196 --> 00:37:39,756
Speaker 15: other ways.

580
00:37:40,396 --> 00:37:43,276
Speaker 2: Tim offered me a take on his brother that was

581
00:37:43,396 --> 00:37:47,836
Speaker 2: neither rat nor hero, but something else altogether.

582
00:37:48,356 --> 00:37:49,036
Speaker 10: I'm afraid that.

583
00:37:50,876 --> 00:37:53,876
Speaker 15: That what matters most of all is just that he's known,

584
00:37:55,796 --> 00:38:02,236
Speaker 15: that he's known, and the goodness is almost irrelevant. I'm

585
00:38:02,276 --> 00:38:08,476
Speaker 15: sorry to say. The most important thing is that, look,

586
00:38:08,516 --> 00:38:14,356
Speaker 15: I am a big man. Look I am somebody. I

587
00:38:14,356 --> 00:38:17,636
Speaker 15: can do really horrible things, I can do good things.

588
00:38:18,236 --> 00:38:18,916
Speaker 15: I'm somebody.

589
00:38:20,436 --> 00:38:23,716
Speaker 2: When I relayed all of this back to Bob, word

590
00:38:23,836 --> 00:38:28,116
Speaker 2: for word, to my great surprise, Bob shrugged his shoulders

591
00:38:28,196 --> 00:38:35,156
Speaker 2: and said he's right in a sense. In the year

592
00:38:35,156 --> 00:38:38,756
Speaker 2: that I spent talking with Bob, he was always upbeat

593
00:38:38,796 --> 00:38:42,236
Speaker 2: and quick to laugh. Part of this is just Bob's nature,

594
00:38:42,636 --> 00:38:44,676
Speaker 2: but I think he was also kind of selling me

595
00:38:44,756 --> 00:38:47,556
Speaker 2: on his story, as if to say, look at me,

596
00:38:48,036 --> 00:38:50,876
Speaker 2: I live quite a life, didn't I? And he had.

597
00:38:51,716 --> 00:38:54,996
Speaker 2: But when I visited Bob in person and saw his

598
00:38:55,076 --> 00:38:58,196
Speaker 2: cubby hole and the roommate who didn't really know him

599
00:38:58,516 --> 00:39:02,076
Speaker 2: or cared to know him, I got a different feeling entirely.

600
00:39:03,196 --> 00:39:07,316
Speaker 2: Bob's bravada was gone, and in its place was an

601
00:39:07,316 --> 00:39:11,676
Speaker 2: air of defeat and almost disbelief, as if he couldn't

602
00:39:11,716 --> 00:39:14,716
Speaker 2: quite fathom that this is how things had turned out.

603
00:39:16,276 --> 00:39:18,636
Speaker 2: I asked Bob if there was any part of him

604
00:39:18,636 --> 00:39:21,556
Speaker 2: that regretted what he'd done, if he could go back

605
00:39:21,596 --> 00:39:24,796
Speaker 2: in time, would he have done it differently? Not flipped

606
00:39:24,796 --> 00:39:25,156
Speaker 2: at all?

607
00:39:26,636 --> 00:39:31,276
Speaker 4: Absolutely, I mean absolutely. The day I put on that

608
00:39:31,356 --> 00:39:36,436
Speaker 4: wire it was all over. I knew it was all over.

609
00:39:38,036 --> 00:39:39,996
Speaker 4: I knew that, you know, my life could never be,

610
00:39:40,196 --> 00:39:42,996
Speaker 4: But I never dreamed it would be as bad as God.

611
00:39:43,636 --> 00:39:46,196
Speaker 4: I'm no better rop than some of those beggars out

612
00:39:46,196 --> 00:39:50,596
Speaker 4: there in the street, and I'd better not even think

613
00:39:50,636 --> 00:39:52,876
Speaker 4: about it, because again, it is the way it is.

614
00:39:53,476 --> 00:39:55,836
Speaker 4: So I mean to say, I wish I could have

615
00:39:55,956 --> 00:39:57,196
Speaker 4: changed that are you kidding me.

616
00:39:57,356 --> 00:40:01,636
Speaker 12: I mean, I'm trying to understand how you think about

617
00:40:01,636 --> 00:40:03,756
Speaker 12: your own life. If the defining thing in your life

618
00:40:03,796 --> 00:40:05,076
Speaker 12: is the thing you wish you hadn't done.

619
00:40:05,836 --> 00:40:10,556
Speaker 4: You've seen my life now. Think about that. You've seen

620
00:40:10,636 --> 00:40:15,356
Speaker 4: my life now, and you can't understand how I wished

621
00:40:15,396 --> 00:40:18,636
Speaker 4: I hadn't done that. That makes no sense.

622
00:40:19,476 --> 00:40:22,636
Speaker 12: Well, I understand it. It's not that I don't understand it.

623
00:40:23,516 --> 00:40:24,036
Speaker 4: I just.

624
00:40:25,716 --> 00:40:27,236
Speaker 12: Trying to wrap my head around it, that's all.

625
00:40:27,356 --> 00:40:31,916
Speaker 4: But you know, again, I don't know. I'm just saying that.

626
00:40:31,956 --> 00:40:35,156
Speaker 4: There's no question in my mind. I'd be an idiot

627
00:40:35,196 --> 00:40:37,956
Speaker 4: to say, gee, I'm glad that I, you know, destroyed myself,

628
00:40:39,076 --> 00:40:42,036
Speaker 4: and that's what I wound up doing. I destroyed. Bob

629
00:40:42,156 --> 00:40:46,036
Speaker 4: Cooley is no longer. This is not Bob Cooley name

630
00:40:46,076 --> 00:40:49,356
Speaker 4: wise or even otherwise. What do you mean they left?

631
00:40:49,396 --> 00:40:52,756
Speaker 4: Bob Cooley was that person back there in Chicago that

632
00:40:52,876 --> 00:40:55,276
Speaker 4: everybody came to when they had trouble and was able

633
00:40:55,316 --> 00:40:57,756
Speaker 4: to help all kinds of people and be able to

634
00:40:57,756 --> 00:41:01,516
Speaker 4: do whatever he damned pleased, never worried about getting arrested

635
00:41:01,596 --> 00:41:04,676
Speaker 4: or getting parking tickets or anything whatever I wanted.

636
00:41:04,836 --> 00:41:05,756
Speaker 12: What is Bob Cooley.

637
00:41:05,796 --> 00:41:11,516
Speaker 4: Now just just to you know, somebody waiting to die.

638
00:41:12,516 --> 00:41:18,076
Speaker 4: That pretty much sums it all up right now at

639
00:41:18,076 --> 00:41:20,196
Speaker 4: this stage. I mean, they you kidding me? What is it?

640
00:41:20,316 --> 00:41:21,476
Speaker 4: He's nobody, he's nothing.

641
00:41:24,236 --> 00:41:27,596
Speaker 2: Hearing him talk like this, I had to wonder once

642
00:41:27,676 --> 00:41:31,436
Speaker 2: again why Bob had flipped in the first place. What

643
00:41:31,516 --> 00:41:35,156
Speaker 2: had he been hoping for. There were so many different theories,

644
00:41:35,316 --> 00:41:39,276
Speaker 2: and Bob himself kind of waffled on this question, offering

645
00:41:39,316 --> 00:41:43,356
Speaker 2: different explanations on different days. It was to clean up

646
00:41:43,396 --> 00:41:46,316
Speaker 2: the city, it was to heed the advice of his

647
00:41:46,476 --> 00:41:49,996
Speaker 2: dying father. He was to stand up to Pat Marcy,

648
00:41:50,156 --> 00:41:52,996
Speaker 2: who was a bully. And it's true Bob did not

649
00:41:53,196 --> 00:41:56,796
Speaker 2: like being pushed around. But my feeling about all of

650
00:41:56,836 --> 00:42:02,676
Speaker 2: these was yeah, maybe, but they seemed like partial explanations

651
00:42:02,956 --> 00:42:08,236
Speaker 2: at best. The theory I heard the most was that

652
00:42:08,356 --> 00:42:11,276
Speaker 2: Bob owed to the mob. That's what was in all

653
00:42:11,316 --> 00:42:15,116
Speaker 2: the papers at the time. But I don't really buy it.

654
00:42:15,596 --> 00:42:18,556
Speaker 2: I mean, think about the timeline. Bob flipped back in

655
00:42:18,636 --> 00:42:22,036
Speaker 2: nineteen eighty six, he fled town in nineteen eighty nine.

656
00:42:22,716 --> 00:42:26,396
Speaker 2: So put yourself in Bob's shoes if you were truly

657
00:42:26,436 --> 00:42:29,236
Speaker 2: worried about owing money to the mob, and you were

658
00:42:29,276 --> 00:42:31,916
Speaker 2: spooped that some goons were going to break your legs

659
00:42:32,036 --> 00:42:35,596
Speaker 2: were worse, Why would you flip and then stick around

660
00:42:35,676 --> 00:42:39,236
Speaker 2: town for the next three and a half years. You wouldn't.

661
00:42:41,076 --> 00:42:45,316
Speaker 2: It's true Bob was a gambler, and I think that

662
00:42:45,436 --> 00:42:48,836
Speaker 2: this does in fact explain what he did. I kept

663
00:42:48,876 --> 00:42:51,236
Speaker 2: thinking back to what Bob told me on the very

664
00:42:51,276 --> 00:42:54,396
Speaker 2: first day that we talked, that he'd been walking down

665
00:42:54,396 --> 00:42:57,556
Speaker 2: the street to get a Deli sandwich, he'd seen the

666
00:42:57,556 --> 00:43:02,836
Speaker 2: Prosecutor's office and just walked in on an impulse. And

667
00:43:02,956 --> 00:43:07,596
Speaker 2: now I could see it. Here's Bob the gambler, because

668
00:43:07,676 --> 00:43:10,596
Speaker 2: walking into that office was, in some ways the biggest

669
00:43:10,636 --> 00:43:14,356
Speaker 2: gamble of all. He was wagering his life. He was

670
00:43:14,396 --> 00:43:19,276
Speaker 2: betting that he could almost magically save himself and perhaps

671
00:43:19,636 --> 00:43:22,876
Speaker 2: the city of Chicago while he was at it. Not

672
00:43:22,956 --> 00:43:26,196
Speaker 2: a sensible bet, a real long shot, you might say,

673
00:43:26,876 --> 00:43:45,836
Speaker 2: which is probably exactly why he did it. One day,

674
00:43:45,916 --> 00:43:47,996
Speaker 2: toward the end of my visit with Bob, we had

675
00:43:48,076 --> 00:43:50,476
Speaker 2: lunch together at the little place where I was staying.

676
00:43:51,436 --> 00:43:54,156
Speaker 2: I ordered her some pizza, which we didn't finish, and

677
00:43:54,196 --> 00:43:56,836
Speaker 2: I was about to throw the leftover slices out when

678
00:43:56,876 --> 00:44:01,116
Speaker 2: Bob stopped me, no save those. He told me he

679
00:44:01,196 --> 00:44:02,756
Speaker 2: wanted to feed the wildlife.

680
00:44:03,196 --> 00:44:04,196
Speaker 12: Why do you like to do it?

681
00:44:04,796 --> 00:44:07,156
Speaker 4: Because I've been doing it all my life pretty much.

682
00:44:07,196 --> 00:44:09,436
Speaker 4: I like to feed the animals.

683
00:44:09,836 --> 00:44:10,076
Speaker 10: Why.

684
00:44:11,076 --> 00:44:14,636
Speaker 4: I'll be rewarded down the road for it.

685
00:44:14,636 --> 00:44:16,076
Speaker 12: It's always something for something.

686
00:44:16,196 --> 00:44:19,796
Speaker 4: I like you. I like animals. You know, I feel

687
00:44:19,796 --> 00:44:21,356
Speaker 4: bad when I see him out there. You know they

688
00:44:21,436 --> 00:44:24,996
Speaker 4: might be going hungry. It's always been my nature. I

689
00:44:25,156 --> 00:44:25,636
Speaker 4: just do it.

690
00:44:27,276 --> 00:44:29,636
Speaker 2: We took the scraps of pizza and drove over to

691
00:44:29,676 --> 00:44:32,956
Speaker 2: one of Bob's favorite spots. It was at the edge

692
00:44:32,956 --> 00:44:35,716
Speaker 2: of a parking lot next to a strip mall. He

693
00:44:35,796 --> 00:44:39,716
Speaker 2: came here often. This is kind of a random spot.

694
00:44:39,756 --> 00:44:40,756
Speaker 5: Why do you pick this spot?

695
00:44:40,796 --> 00:44:46,276
Speaker 4: We're like, we're at a over You'll see them all

696
00:44:46,316 --> 00:44:48,356
Speaker 4: over here over on the other side. There, they've got

697
00:44:48,356 --> 00:44:52,676
Speaker 4: a fast food restaurant, two fast food restaurants, and that's

698
00:44:52,676 --> 00:44:54,356
Speaker 4: where the birds seem to migrate.

699
00:44:58,156 --> 00:45:01,676
Speaker 2: I stood there and watched as the birds flocked around him,

700
00:45:01,716 --> 00:45:06,356
Speaker 2: swirling and chirping. For a moment, he seemed genuinely content.

701
00:45:09,156 --> 00:45:11,836
Speaker 2: The whole scene reminded me of how back when he

702
00:45:11,916 --> 00:45:14,916
Speaker 2: was still in Chicago, wearing a wire. He used to

703
00:45:14,916 --> 00:45:19,316
Speaker 2: feed the baby raccoons with no ulterior motives, just a

704
00:45:19,356 --> 00:45:24,556
Speaker 2: pure and simple act, a real rarity, because nothing in

705
00:45:24,636 --> 00:45:26,756
Speaker 2: Bob's life was ever simple.

706
00:45:38,036 --> 00:45:41,076
Speaker 12: Your herds are up there at the corner, looks like yeah.

707
00:45:40,916 --> 00:45:43,796
Speaker 4: No, they for some reason, they always fly away and

708
00:45:43,836 --> 00:45:45,716
Speaker 4: then they come back. But you'll get them cross the

709
00:45:45,716 --> 00:45:52,156
Speaker 4: way over here and they'll come back and get it.

710
00:45:55,516 --> 00:46:05,876
Speaker 4: The braver ones get fed the most. There's some of

711
00:46:05,956 --> 00:46:07,036
Speaker 4: them coming up above.

712
00:46:50,116 --> 00:46:53,556
Speaker 2: Deep Cover is produced by Jacob Smith and Amy Gaines

713
00:46:53,956 --> 00:46:58,556
Speaker 2: and edited by Karen Chakerji. Our senior editor is Jen Guera.

714
00:46:59,236 --> 00:47:02,596
Speaker 2: Original music and the deep Cover theme was composed by

715
00:47:02,676 --> 00:47:08,076
Speaker 2: Luis Garra, with performances by Luise Audrian Terrasas, Alan Fajardo,

716
00:47:08,396 --> 00:47:12,876
Speaker 2: Mi Longoria, and Jimmy Messer. Flawn Williams is our engineer.

717
00:47:13,276 --> 00:47:15,836
Speaker 2: Our art this season was drawn by Cheryl Cook and

718
00:47:15,916 --> 00:47:19,916
Speaker 2: designed by Sean Carney. Mia Lobel is our executive producer.

719
00:47:20,476 --> 00:47:25,316
Speaker 2: Special thanks to Heather Fain, John Schnarz, Carly Migliori, Maya Caning,

720
00:47:25,636 --> 00:47:30,996
Speaker 2: Christina Sullivan, Eric Sandler, Mary Beth Smith, Brant Haynes, Maggie Taylor,

721
00:47:31,276 --> 00:47:36,796
Speaker 2: Nicole Morano, Megan Larson, Morgan Ratner, Royston Deserve, Lucy Sullivan,

722
00:47:37,236 --> 00:47:43,276
Speaker 2: Edith Russello, Riley Sullivan, Jen Sanchez, Jason Gambrell, Martin Gonzalez,

723
00:47:43,636 --> 00:47:49,236
Speaker 2: and Jacob Weisberg. Additional special thanks to Jill Gillette, Travis Dunlap,

724
00:47:49,516 --> 00:47:55,116
Speaker 2: Maggie de Poy, Bill Hogan, David Grossman, Mike Shephard, Jim Wagner,

725
00:47:55,436 --> 00:48:01,516
Speaker 2: Denny Cherrillo, Lisa Chase Patterson, and Michael Deutsch. Also Christian McNally,

726
00:48:01,836 --> 00:48:07,356
Speaker 2: Isabel Vasquez, Jesse de Bartolomeo, Jane Miliotis, Sarah Kraditch, and

727
00:48:07,396 --> 00:48:53,556
Speaker 2: the National Archives at CHU Chicago. I'm Jake Halbert. If

728
00:48:53,596 --> 00:48:56,116
Speaker 2: you like this season of deep Cover, then you should

729
00:48:56,156 --> 00:48:59,436
Speaker 2: really check out our first season, The Drug Wars, which

730
00:48:59,516 --> 00:49:02,436
Speaker 2: tells the story of an FBI agent who goes under

731
00:49:02,436 --> 00:49:05,516
Speaker 2: cover with a biker gang and uncovers a series of

732
00:49:05,596 --> 00:49:08,556
Speaker 2: clues that leads to a war, I mean, a full

733
00:49:08,596 --> 00:49:14,076
Speaker 2: scale invasion. Also check out Pushkin's other true crime podcasts,

734
00:49:14,636 --> 00:49:18,556
Speaker 2: Lost Hills and Bad Women. These shows and more are

735
00:49:18,596 --> 00:49:23,476
Speaker 2: available ad free for Pushkin Plus subscribers. To find more

736
00:49:23,516 --> 00:49:29,516
Speaker 2: Pushkin podcasts, listen on the iHeartRadio app, Apple Podcasts, or

737
00:49:29,756 --> 00:49:33,836
Speaker 2: wherever you listen to podcasts,