Speaker 1: Pushkin Jake Alpern here before we get started, I wanted
Speaker 1: you to know that deep Cover Season two will be
Speaker 1: dropping weekly on Mondays, but the full season is available
Speaker 1: right now ad free for Pushkin Plus subscribers. That's all
Speaker 1: ten episodes right away. Fine Pushkin Plus on the deep
Speaker 1: Cover show page in Apple Podcasts, or at pushkin dot Fm.
Speaker 1: Previously on deep Cover. In nineteen eighty six, Bob Cooley,
Speaker 1: a Chicago lawyer who had worked for the mob, walked
Speaker 1: into the office of a federal prosecutor and offered to cooperate.
Speaker 1: Prosecutors were mystified why was he doing this? Up until
Speaker 1: this moment, Bob Cooley had a reputation as a flashy
Speaker 1: criminal defense lawyer who helped at least one person get
Speaker 1: away with murder. Literally. In nineteen seventy seven, Bob vixed
Speaker 1: the trial of Harry Alaman, a legendary mafia hit man.
Speaker 1: The judge is not guilty. Verdict provoked outrage from both
Speaker 1: the media and the public. They couldn't even speak, that's
Speaker 1: how the man and how livid they were. They could
Speaker 1: not believe that this judge didn't fight him guilty. The
Speaker 1: place went into a piano, but for the mob. This
Speaker 1: case proved Bob's worth. He could be their ace in
Speaker 1: the hole. Not long ago, I called up this guy
Speaker 1: who used to know Bob. We're going to call him Nick.
Speaker 1: Nick is in his real name. It's just a nickname
Speaker 1: that we're using to protect his identity. Bob Cooley was
Speaker 1: the best man. He was good at cooks and cases,
Speaker 1: and hey, they knew how good he was if. I
Speaker 1: always said, if I get some deep shit, it's going
Speaker 1: to be a Bob, and Nick was always on the
Speaker 1: edge of some deep shit. I was a captain and
Speaker 1: the mob not don't be waving my flag, but I
Speaker 1: was one of the smarter guys out there. My crew
Speaker 1: was known as the Enforcement Crew, and we we would
Speaker 1: go and do the dirty jobs that other people couldn't handle.
Speaker 1: Back in the day, Nick's specialty was collecting unjuice loans.
Speaker 1: I asked him how he operated. What he'd do if
Speaker 1: I owed him money it didn't pay up. Nick says
Speaker 1: he'd start by asking for it politely. But if that
Speaker 1: didn't work, well, I tell you, Jake, you know, if
Speaker 1: you got twenty four hours to come up with that money,
Speaker 1: if you don't come up the money, I'm gonna come
Speaker 1: bust your fucking head or pop your eyes out and
Speaker 1: gat him like grapes any and he'll lingo like that,
Speaker 1: any any kind of Sometimes you gotta grab the person
Speaker 1: by the throat. Sometimes you gotta grab you know, sometimes
Speaker 1: you gotta you know, knock him out to break their
Speaker 1: lose all defense. What the scenario is, perhaps inevitably Nick
Speaker 1: or one of his guys would get in trouble with
Speaker 1: the cops. When that happened, he knew he could count
Speaker 1: on Bob. And the proof was the Harry Laman case.
Speaker 1: When you get a guy that's a hitman and you
Speaker 1: get him off of a major case, a murder case,
Speaker 1: I mean, everybody's gonna say. Everybody says, hey, I get
Speaker 1: in trouble and going to Bob, which kind of makes
Speaker 1: you wonder how'd Bob become the kind of guy who'd
Speaker 1: do this anyway, who'd fix cases for the Mob and
Speaker 1: think you could get away with it. In this episode,
Speaker 1: we're going to take a hard look at how Bob
Speaker 1: became Bob and where it all started to go wrong
Speaker 1: for him. I'm Jake Halpern, and this is Deep Cover
Speaker 1: mob Land episode four. The favorite son Bob had taken
Speaker 1: a big risk by getting involved with the Harry Lamon trial. First,
Speaker 1: he'd made a risky promise to Pat Marcy, the mob's
Speaker 1: political czar, that he could fix the case. He'd also
Speaker 1: assured Harry that all would go well, and he targeted
Speaker 1: a judge with an honorable reputation. The whole thing, start
Speaker 1: to finish was very bold, but somehow or another, it
Speaker 1: all worked out for Bob and the outfit. Anyhow, according
Speaker 1: to Bob, Harry the hitman, essentially became his pr guy
Speaker 1: told him, listen, give me some of your cards, he said,
Speaker 1: because I got all kinds of business, I got all
Speaker 1: kinds of people. Now, he says, you're going to be
Speaker 1: the top lawyer in the city. Business was better than
Speaker 1: ever for Bob, but still he kept his guard up.
Speaker 1: Bob says he always assumed everyone he met was wearing
Speaker 1: a wire. This kind of paranoia kept him safe and
Speaker 1: with new clients. Bob also avoided overpromising. He said, well,
Speaker 1: but can you guarantee something? I can't guarantee anything. I'll
Speaker 1: just do the best that I can. But his best
Speaker 1: was plenty good enough. I've got thousands of friends, I
Speaker 1: mean thousands of friends in the city of Chicago. Bob
Speaker 1: was living it up. I'm living a fantastic life. I've
Speaker 1: got all the friends in the world. I've got sweethearts
Speaker 1: coming up and down and all around. Sometimes I got
Speaker 1: this sense from talking to Bob that being a lawyer
Speaker 1: for the Mob was all glamor that he lived a
Speaker 1: charmed life and look in many ways he did. According
Speaker 1: to Bob, unless he was trying a case, his workdays
Speaker 1: were generally over by midday. Then he'd grabbed lunch. Next
Speaker 1: he'd have a steam bath and then a massage. In
Speaker 1: the summer, he might hang out at his poolside cabana.
Speaker 1: Otherwise he'd go back to the office, head to the
Speaker 1: conference room, where he'd play cards. Jim was his game.
Speaker 1: Then night he hit the clubs, or he fled to Vegas.
Speaker 1: One time even had dinner with Frank Sinatra and picked
Speaker 1: up the tab. This was Bob's life, but he was
Speaker 1: still a lawyer who needed an office in a filing
Speaker 1: cabinet and even a pencil sharpener, and he had this too.
Speaker 1: He shared a workspace downtown with a few other lawyers,
Speaker 1: including his brother Dennis Cooley. They actually use the same desk,
Speaker 1: sort of like a timeshare. Well, we were in the
Speaker 1: same office. He had literally in the same room and
Speaker 1: would just use it sometimes he'd use it sometimes. Dennis
Speaker 1: was four years younger than Bob. He also started off
Speaker 1: as a police officer, then became a lawyer. But here
Speaker 1: their paths diverged sharply. Dennis went on to become a prosecutor,
Speaker 1: and a good one. At some point he ran an
Speaker 1: entire division. I talked to a bunch of people who
Speaker 1: knew Dennis from back then, and they all pretty much
Speaker 1: said the same thing. Dennis was an honest and honorable guy. Eventually,
Speaker 1: Dennis decided to go into private practice, and like his brother,
Speaker 1: he became a criminal defense lawyer. But unlike Bob, Dennis
Speaker 1: was a clean criminal defense lawyer, which wasn't easy. He
Speaker 1: was practicing law in a system where so many of
Speaker 1: his competitors were guys who would place bribes. Of course,
Speaker 1: I resented it, Yes, he absolutely resented it. I resented
Speaker 1: the fact that I had to work hard from my
Speaker 1: money and these other guys didn't. You know, when you're
Speaker 1: practicing law and you know you're a better attorney than
Speaker 1: the next guy, and yet the next guy seems to win.
Speaker 1: All these cases in front of these particular judges, and
Speaker 1: it's like, this is bullshit, but that's the way it was.
Speaker 1: Dennis says that he didn't know the full extent of
Speaker 1: Bob's shady dealings, but there were moments when he did
Speaker 1: get a sense for what his brother was up to.
Speaker 1: You know, some of the people who would who would
Speaker 1: come in were not the kind of people I would
Speaker 1: normally end up with as a client. Some of them were,
Speaker 1: you know, outright scary looking. You know, I just kept
Speaker 1: I just kept the hell away from him. Did you
Speaker 1: ever pull Bob aside and say, like, what are you doing?
Speaker 1: Cut it out? I don't. That would have been a complete,
Speaker 1: total waste of time. I don't think he would have
Speaker 1: listened to me. Interestingly, there were things about Bob that
Speaker 1: Dennis seemed to admire. He said that Bob was really
Speaker 1: good in front of a jury, that he really knew
Speaker 1: how to connect with the jurors win them over. I
Speaker 1: found believable. I mean, Bob could be very charming. He
Speaker 1: also says that Bob wasn't afraid to stand up to bullies.
Speaker 1: This was true when Bob was a kid. He was short.
Speaker 1: Back then, people called him shrimp, which drove him crazy.
Speaker 1: Dennis says, one time Bob got in a fight with
Speaker 1: this much bigger kid. He was so much different in
Speaker 1: size than this big guy. He would literally have to
Speaker 1: jump up to hit him in the face, and he
Speaker 1: would do that, and he backed the big kid off.
Speaker 1: And that kind of left the compression with me. How
Speaker 1: aggressive he could be, you know, and how he wouldn't
Speaker 1: back off from certain challenges. It also seemed telling to
Speaker 1: me that Dennis found all of these reasons to admire Bob.
Speaker 1: Dennis was a guy who saw the best in others,
Speaker 1: even his shady brother. So there were the Coolie brothers,
Speaker 1: Bob and Dennis sharing the exact Sam desk. It was
Speaker 1: a powerful image. They seemed to be symbolic of the
Speaker 1: two realms of the Chicago legal system, the clean and
Speaker 1: the dirty, operating side by side, morally opposed but hopelessly interconnected.
Speaker 1: And for me, it also raised the question how had
Speaker 1: these two brothers turned out so differently. The Coolies were
Speaker 1: known as a family of honest cops. Bob's parents were
Speaker 1: devoutly religious, So what exactly happened with Bob. To really
Speaker 1: understand Bob Cooley, We're going to go deep into his
Speaker 1: relationship with his father. But I want to start by
Speaker 1: giving you a picture of what the Coolie family was
Speaker 1: like back when Bob was a kid. And to do this,
Speaker 1: I got to take you back to the nineteen forties.
Speaker 1: The family lived on the South side of Chicago in
Speaker 1: an Irish Catholic neighborhood. It was a good childhood. Actually
Speaker 1: we were nine kids, so you know, so that is
Speaker 1: an experience in itself. That's Tim Cooley, another one of
Speaker 1: Bob's six brothers. He lives in Vermont now, and as
Speaker 1: I tried to make sense of Bob's childhood, he became
Speaker 1: my guide, my guru. Really. I am a massage therapist
Speaker 1: and a yoga teacher, two things which really really make
Speaker 1: me happy. I work at a gay run retreat center
Speaker 1: doing yoga and massage. There. It's a community that is
Speaker 1: about helping people grow, basically, helping people be the fullest
Speaker 1: that they can be. Tim is Bob's younger brother, and
Speaker 1: he spent a lot of time reflecting on his child
Speaker 1: hood and the Coolie family. He told me that their father,
Speaker 1: Jim Coolie, was extremely pious. All the Coolie kids said
Speaker 1: this by the way that their dad made them pray together.
Speaker 1: Jim Cooley the dad actually went to a Catholic seminary
Speaker 1: and studied for the priesthood before deciding to become a
Speaker 1: cop and eventually a detective. And by all accounts, he
Speaker 1: was an honest policeman, never took a bribe and didn't
Speaker 1: look for trouble. Well, because my father was a really gentleman.
Speaker 1: He was like the least macho man I've ever met
Speaker 1: in my life. To some degree, Yeah, he really was.
Speaker 1: He was. I mean, he had an Irish temper mind,
Speaker 1: you you know, so he would he would get angry
Speaker 1: at times or whatever. But he was very he was
Speaker 1: very mild. To be clear, Tim doesn't have any illusions
Speaker 1: about his father. He told me straight up his dad
Speaker 1: could be a racist. But for the most part, Tim
Speaker 1: says he has fond memories of growing up in the
Speaker 1: coolie household. We never felt like we were without you
Speaker 1: know we, I mean, we were just sort of the
Speaker 1: same as everybody else. We thought we would have called
Speaker 1: ourselves middle class, I guess. On the other hand, Bob
Speaker 1: told me that his family grew up very poor. I
Speaker 1: never had clothes. I never had new clothes as I
Speaker 1: grew up. All my clothes were. You know, my mother
Speaker 1: would be over basically at the school, begging, begging for
Speaker 1: stuff because she had two you know, for the you know,
Speaker 1: for the sake of the kids. And I was really
Speaker 1: angry for a long time being born into a family
Speaker 1: with all these kids. I really was. I was angry
Speaker 1: at God because so many of people I knew had
Speaker 1: so much more than me. The worst for Bob was
Speaker 1: when his mother took him shopping for groceries and scoured
Speaker 1: the shelves for dented cans so she could ask the
Speaker 1: clerk for a discount for a few pennies off. This
Speaker 1: mortified Bob, I asked him about this. There you have
Speaker 1: Bob and me a nutshell. The difference is that I
Speaker 1: would admire my mother for that, whereas Bob cared more
Speaker 1: about how things looked or how things seemed to others.
Speaker 1: I would say than I did as a kid. Bob
Speaker 1: worked all kinds of jobs, but that pocket money only
Speaker 1: got him so far, and he was still angry and
Speaker 1: frustrated by what he didn't have. And that sort of
Speaker 1: explains on some level, his drive to be financially successful.
Speaker 1: Whatever it took for him to get that. He was
Speaker 1: always driven on some level driven, and I guess you
Speaker 1: would say a bit of a troublemaker quite frankly. I
Speaker 1: mean he would be good at getting out of trouble
Speaker 1: by hook or by crook basically, but he was always
Speaker 1: sort of working an angle, and Bob admits to this.
Speaker 1: He describes his childhood as one long tale of rule breaking,
Speaker 1: cheating on tests, starting fights, skipping church. Let me tell you,
Speaker 1: when it came to the coolie household Santa did not
Speaker 1: have to check his list twice. And given all of this,
Speaker 1: you might think that Bob's hero was well, Jesse James
Speaker 1: or John Dillinger or some other scoff Law. Nope. Interestingly,
Speaker 1: the one person that I always heard Bob speak of
Speaker 1: with almost unflagging admiration was actually his dad. He extolled
Speaker 1: his dad's virtues. I couldn't take when I was a
Speaker 1: kid growing up. I'd go in there and steal candy
Speaker 1: and stuff like that because I was hungry, and because
Speaker 1: you know, I couldn't. I have no money in my pockets.
Speaker 1: My dad would never have done something like that. Did
Speaker 1: you feel any sense of guilt or any sense that
Speaker 1: you weren't living up to your dad's standards? No, no,
Speaker 1: not at all. Honestly, this surprised me, given how much
Speaker 1: he revered his dad. It seemed like maybe Bob would
Speaker 1: just have a little bit of a hard time looking
Speaker 1: his dad in the eye, or feel just a bit
Speaker 1: cheapish about his transgressions. Nope, says Bob. There was one occasion, however,
Speaker 1: when Bob seemed to push his father too far, when
Speaker 1: he really tested the limits of their relationship, and as
Speaker 1: you're about to hear, it was a defining moment for Bob.
Speaker 1: It was a Sunday. Bob says he was about fourteen
Speaker 1: years old. He'd been out in the alleyway doing what
Speaker 1: kids did before cell phones, namely, throwing rocks. Bob ended
Speaker 1: up breaking a neighbor's window. The neighbor walks over to
Speaker 1: Bob's house, talks to Bob's mom, tells her what happened.
Speaker 1: In a panic, Bob blames his brother Bill, says, Bill
Speaker 1: broke the window. This lie, It doesn't hold up. The
Speaker 1: neighbor points to Bob says he's the one who did this.
Speaker 1: Bob says his mother was furious, and she tells him, basically,
Speaker 1: your father will deal with you when he gets home
Speaker 1: from work. A little while later, dad arrives and his
Speaker 1: mom launches right into it. Jem, that's this is a
Speaker 1: you know, he's out of control. This is thing going
Speaker 1: on too long? Time you give and that she tells
Speaker 1: him what happened. His dad is not happy. I mean here,
Speaker 1: he's come back from a long day of work, walking
Speaker 1: the streets and forcing the law, and he learns that
Speaker 1: his troublemaker's son has broken a window and then framed
Speaker 1: his brother. And mom is pissed. Something has to be
Speaker 1: done about this, so his dad escorts Bob to the bedroom.
Speaker 1: We go in there, he gets his police stuff, there's
Speaker 1: old policeman stuff, and then he goes and he closes
Speaker 1: the door and he tells me, bend over the bed.
Speaker 1: I bend over the bed and he starts hitting the bed.
Speaker 1: Mind you, his dad is not actually whipping Bob. He's
Speaker 1: just pretending to whip him. And you could hear this thump, thump, thump,
Speaker 1: And I start hollering, pretending I've heard him, and I
Speaker 1: guess I'm I'm screaming real loud. You know. Oh my
Speaker 1: mother now thinks she's beating me half to death. I
Speaker 1: guess she opens the door. I laugh now I didn't laugh.
Speaker 1: Then she opens the door and here he is, and
Speaker 1: here I am, and I look up and she goes ballistic.
Speaker 1: She goes ballistic because she's caught onto the ruse. And
Speaker 1: at this point she's not happy with Bob or her husband.
Speaker 1: What's the matter with you, that's why he's the way
Speaker 1: he is or whatever? And my dad got it so
Speaker 1: shook my dad up. He started hitting me with the belt.
Speaker 1: I got into the bed because I mean he was
Speaker 1: like a madman for a minute. And when I come
Speaker 1: under the bed, he grabbed the bed with one hand,
Speaker 1: picked the bed up, started trying to hit me under
Speaker 1: the bed another couple of times. And I'm crying because
Speaker 1: I mean, it's it's it hurt, It really hurt. And
Speaker 1: then get in your room. I go in the room.
Speaker 1: H m hm, Wait, Bob, what got you? What? What
Speaker 1: got you so upset all of a sudden? What did that?
Speaker 1: What was that about? I just saw him coming in
Speaker 1: the room. I just saw him coming in the room.
Speaker 1: He came in the room and he was crying, I mean,
Speaker 1: I mean crying and he comes over. H I'm I'm
Speaker 1: laying in the bed and he's on his knees apologized
Speaker 1: to debate for her doing what he is, and all
Speaker 1: the times that we talked, this is one of the
Speaker 1: only times I heard Bob like this. Somehow he was
Speaker 1: shaken by this memory of his father, the good cop,
Speaker 1: the pious man, the almost priest who's been flummixed by
Speaker 1: his son's constant transgressions, the gentle dad who finally been
Speaker 1: pushed to the point of violence, and then, in a
Speaker 1: fit of shame, the distraught man who'd come back and
Speaker 1: asked for his son's forgiveness. Remembering all this seemed to
Speaker 1: upset Bob horribly, and the pain it seemed to me, anyhow,
Speaker 1: was not in his father's disappointment, not in what his
Speaker 1: father had done to him, but in what he had
Speaker 1: done to his father, and the love his father still
Speaker 1: felt for him despite it all. I don't think, you know,
Speaker 1: I don't know of anybody who has a more interesting
Speaker 1: relationship with a father, probably than me, Because like I said,
Speaker 1: I did all the things I did as a kid.
Speaker 1: You would think he would be, you know, I'd be
Speaker 1: I'd be the worse in his mind of the kids.
Speaker 1: And yet even though I'm always getting in trouble and
Speaker 1: doing all these things, he always treated me as his
Speaker 1: favorite in every way. You know, the fact he wouldn't
Speaker 1: discipline me, He didn't believe in laying a hand on me,
Speaker 1: things like that. It was an unbelievable relationship that I had.
Speaker 1: Did you think he was Do you think he was
Speaker 1: disappointed in you when you were up to no good?
Speaker 1: The fact is he was not. I mean, I was
Speaker 1: still his favorite son in every way. I mean, what
Speaker 1: where can I say? Bob told me this repeatedly, that
Speaker 1: he was his dad's favorite son. This got me thinking
Speaker 1: about what kind of dad, Jim cool he was. So
Speaker 1: I asked Tim, My father loved all his sons, has
Speaker 1: loved all his children. He really did, but it was
Speaker 1: it wasn't a very demonstrative sort of love, you know.
Speaker 1: I mean he would he would tell each one of us,
Speaker 1: you know, you're my favorite son. You know, you'd roll
Speaker 1: your eyes and you'd know, you would you know that
Speaker 1: he was meaning, he was meaning something to be you know,
Speaker 1: to be meaningful. I mean, he was basically saying I
Speaker 1: love you, but he had a hard time saying it.
Speaker 1: And here is yet another crucial difference between Bob and Tim.
Speaker 1: When Dad told Bob, you're my favorite son, Bob absolutely
Speaker 1: believed him. Took the gesture at face value, almost like
Speaker 1: confirmation that despite everything he'd done, that he hadn't come
Speaker 1: up short in his father's eyes, that he still always
Speaker 1: had the blessing of the pious man. And for Bob,
Speaker 1: as far as I could tell, this seemed to be
Speaker 1: like a green light. As for their mom, Tim told
Speaker 1: me she was at a loss on how to raise
Speaker 1: Bob and hold him accountable. Bob was such a handful
Speaker 1: that she didn't know how to deal with it, and
Speaker 1: I think she saw him getting away with stuff. And
Speaker 1: I think that has that kind of explains Bob on
Speaker 1: some level, is that he never really paid the consequences
Speaker 1: for his actions, which is why maybe he was willing
Speaker 1: to do actions that were really beyond the pale. Ultimately,
Speaker 1: when Tim told me this, I started to see it.
Speaker 1: Bob grew up in a home where he could flout
Speaker 1: the rules, and he came of age in a city
Speaker 1: where the rules meant even less. There was no accountability
Speaker 1: for Bob anywhere, no one he had to answer to,
Speaker 1: except of course, the mob. Ever, since he was a kid,
Speaker 1: Bob had a rebellious streak. I guess he could say
Speaker 1: he had issues with authority, and that pretty much never changed.
Speaker 1: Even years later, when he was a grown man and
Speaker 1: a lawyer for the Mob, Bob was still throwing rocks
Speaker 1: and breaking windows, testing the limits. And I'm going to
Speaker 1: tell you a story about a situation Bob found himself
Speaker 1: in the real crossroads where he took it upon himself
Speaker 1: to challenge the Mob and its power, which he would
Speaker 1: find out wasn't so wise. There'd be no fake spankings
Speaker 1: for this offense. So it's nineteen eighty one. Bob is
Speaker 1: representing a friend of his, a gangster who'd gotten in
Speaker 1: trouble with the law, a guy named Frank Rannella. And
Speaker 1: one day Bob hears from a prosecutor in the case
Speaker 1: who tells him, essentially, there's something you need to know
Speaker 1: about your client, Frank. He's been a government informant in
Speaker 1: the past. Bob understood immediately that this would be a
Speaker 1: death sentence for Frank. The Mob would murder any insiders
Speaker 1: who cooperated with the FEDS. That was a hard and
Speaker 1: fast rule, But you know how Bob is with rules.
Speaker 1: And besides, for Bob, this whole thing just felt wrong
Speaker 1: in his gut. If somebody told me they were going
Speaker 1: to kill somebody, and I knew that they were going
Speaker 1: to do it. I would have found a way to
Speaker 1: warn them. That's just me. Bob says he decided to
Speaker 1: help his friend and client escape. I drove right to
Speaker 1: Frank's house, and when I went upstairs to his apartment
Speaker 1: and I told him, he puts a gun on me.
Speaker 1: He thinks I'm initially he thinks I'm setting him up,
Speaker 1: and he says, I'm leaving now, and you're walking out
Speaker 1: in front of me. If they're out there, as Bob
Speaker 1: tells it, Frank walks outside, looks around and sees that
Speaker 1: no one is waiting for him, so he realizes this
Speaker 1: does not appear to be a setup, understands that Bob
Speaker 1: was truly just trying to help him. Frank passed away
Speaker 1: over twenty years ago, so I couldn't talk to him
Speaker 1: and get his version of events, but I did track
Speaker 1: down his widow, Faye Ronella. She still remembers Bob's visit.
Speaker 1: He gives he had this air about him, a very
Speaker 1: arrogant above it all, so to speak. I just didn't
Speaker 1: care for him. After Bob arrived, Faye says that he
Speaker 1: and Frank went off to talk in private. I sat
Speaker 1: in the front room while Bob Cooley talked to Frank
Speaker 1: in the bedroom. I wasn't a privy to their conversation.
Speaker 1: Frank later told Faye that he was in trouble. They're
Speaker 1: going to try and get me, is actually what he
Speaker 1: said at them, meaning the mob. I was assuming at
Speaker 1: the time, they're going to try and find a way
Speaker 1: to get me, put me out of the picture if
Speaker 1: I go to court. Frank told her he had to
Speaker 1: get out of town. She was devastated by the news.
Speaker 1: I mean, he was everything to me, even though he
Speaker 1: told me it's the very beginning of our relationship. He says,
Speaker 1: I want you to know something from the get go.
Speaker 1: He says, I'm nothing but a fourteen tarrot bum, A
Speaker 1: fourteen carrot bum, gold on the outside, bum on the inside,
Speaker 1: like a warning to me, you get involved with me,
Speaker 1: this is what you're getting involved with. Okay. And now
Speaker 1: it was almost like Frank's prophecy had come true. Trouble
Speaker 1: had finally arrived at the doorstep of the fourteen carrot
Speaker 1: bum as predicted. Luckily, with Bob's help, Frank had gotten away,
Speaker 1: but now Bob was on the hook. I went back
Speaker 1: and asked Nick the Gangster about this. He remembers when
Speaker 1: all of this happened, and he appreciated the enormity of
Speaker 1: what Bob had done, the risk he had taken. You
Speaker 1: do things like that, you're telling the guy that you're
Speaker 1: gonna he's gonna get whack. Well, you're giving him two avenues.
Speaker 1: If he's got money, he can run. If he doesn't
Speaker 1: have money, or even if he has money, he could
Speaker 1: run run into the arms of the FBI. Meaning you've
Speaker 1: given him a chance to switch sides in order to
Speaker 1: save his own skin. And now he might talk, spill
Speaker 1: his guts. So what Bob had done, it was no
Speaker 1: small thing. There would be consequences. Would Bob have understood
Speaker 1: that when he did that? Yes, oh yeah, Bob knod
Speaker 1: he interwork, he said, a mob better than some of
Speaker 1: the Bob guys. So what's your sense for why Bob
Speaker 1: did that? Loyalty? Well, Bob's a loyal guy. Bob wasn't
Speaker 1: didn't want anybody to get hurt, and Bob doing that
Speaker 1: he crossed the line big time. Bob understood this, and
Speaker 1: so he wasn't entirely surprised when shortly after this he
Speaker 1: got a tip that his own life was in danger,
Speaker 1: so Bob ran for it. I flew out of town,
Speaker 1: went through California. I was there for about a week,
Speaker 1: and I said to myself, you know enough of this.
Speaker 1: I can't you know, I can't live like this. I
Speaker 1: got to go back and I got to get it
Speaker 1: straightened out. He flew back home and decided to drop
Speaker 1: in on one of the mob bosses, who he knew
Speaker 1: pretty well. It was a Wednesday, and this is important
Speaker 1: because Bob knew that this mob boss went to the
Speaker 1: same restaurant every Wednesday to meet with his guys, sat
Speaker 1: at the same big table right in front of a
Speaker 1: picture window. Bob says, he just shows up unannounced and
Speaker 1: motions for the boss to follow him to the bathroom.
Speaker 1: And here Bob makes the case for why he should
Speaker 1: be allowed to live. I said I did nothing wrong.
Speaker 1: I said, Frank is my friend, he was your friend.
Speaker 1: He did nothing to hurt you people. He wasn't wearing
Speaker 1: a wire and you guys or anything. But I want
Speaker 1: you to know too that you know I did nothing wrong.
Speaker 1: I did what I thought was the right thing, and
Speaker 1: it didn't hurt you people in any way. I said,
Speaker 1: I'm back now. I'm here to stay. I said, if
Speaker 1: anybody thinks for one second, I'm gonna even take a beating,
Speaker 1: I said. You know they're thinking wrong, I said, And
Speaker 1: if I think I got a problem with you, I said,
Speaker 1: you're going to have the fucking problem. And kind of
Speaker 1: amazingly this seemed to work. They let Bob be and
Speaker 1: I have to confess I found this really odd, kind
Speaker 1: of hard to believe. I mean, really, Bob makes his
Speaker 1: impassioned don't you dare kill me speech in the bathroom,
Speaker 1: offers his moral justification for what he's done, throws in
Speaker 1: a bit of tough talk, and all is forgiven. It
Speaker 1: seemed well too easy. So I asked Nick the gangster
Speaker 1: about this. He had to keep on doing what he's
Speaker 1: doing because Bob was a fixer, and they knew he
Speaker 1: was a fixer. He says, Bob didn't really walk free.
Speaker 1: It was more like the mob had done a little
Speaker 1: risk assessment on Bob and decided it wasn't worth killing
Speaker 1: him for now. So as long as Bob kept being useful,
Speaker 1: as long as he kept fixing cases for the mob,
Speaker 1: he was safe. But that meant he couldn't just walk
Speaker 1: away if he said I'm want to quit, I'm gonna
Speaker 1: walk away after everything he'd done or all the cases
Speaker 1: he fix, did he know in this knowledge he has,
Speaker 1: they were definitely killed. But Bob couldn't quit. Bob was
Speaker 1: a lawyer, but he was like a mobster to you
Speaker 1: just can't quit. So yeah, he was trapped, and it
Speaker 1: was a diabolically clever trap if you think about it.
Speaker 1: You got drawn into the mob by the allure of it,
Speaker 1: all the money, the power, the glamor. But you did
Speaker 1: what you were told, and if you tried to assert
Speaker 1: yourself or follow your own code, you did so at
Speaker 1: your own peril, because then the trap tightened, and then
Speaker 1: you really had to do what you were told, or
Speaker 1: one day you ended up in the headlines dead, just
Speaker 1: another mob hit. Throughout this time, In fact, throughout Bob's
Speaker 1: entire tenure as a lawyer for the mob, he says
Speaker 1: he never really discussed what he did with his mom
Speaker 1: or his dad, though there were moments when he got
Speaker 1: a sense for what his dad thought about the mob,
Speaker 1: like once Bob took his parents out to dinner at
Speaker 1: his restaurant, Greco's, and as it so happened, Pat Marcy
Speaker 1: was also there that night with one of his associates.
Speaker 1: If you remember, Marcy was the mob's political tsar, the
Speaker 1: guy who asked Bob to fix the hitman trial. Anyway,
Speaker 1: as Marcy and his friend got up to leave, Bob says,
Speaker 1: his dad turned to him and said, son, I used
Speaker 1: to arrest those people. Bob wasn't sure what to make
Speaker 1: of this. His father's memory had started to go at
Speaker 1: that point, but even so, it was an unsettling thought
Speaker 1: that Bob might be in bed with his father's old enemies.
Speaker 1: Then sometime after this, Bob's father's health took a turn
Speaker 1: for the worse. Bob went to see him in the hospital.
Speaker 1: His dad was in bed and looked very weak. I
Speaker 1: was there for about maybe fifteen twenty minutes, and I
Speaker 1: could see he was getting worse and worse. And that's
Speaker 1: when he suddenly looks at me and he he was like,
Speaker 1: you know, not that lucid for a period of time
Speaker 1: and he just looks up at me and he says, son,
Speaker 1: He says, son, why are you wasting your god given
Speaker 1: talents with these people? These people He didn't have to
Speaker 1: specify who they were. It was almost like he was
Speaker 1: speaking in Bob's code, saying without saying, but Bob, he understood.
Speaker 1: He was talking about all the gangsters and corrupt politicians.
Speaker 1: He was talking about the mob writ large. He was
Speaker 1: asking Bob, what are you doing with these guys? And
Speaker 1: then his father said one more thing. He brought up
Speaker 1: a bit of family history that Bob knew very little about.
Speaker 1: It involved Bob's grandfather, who was also a cop and
Speaker 1: had been killed on the job. He said, you realize
Speaker 1: that my father, the person who killed my father, got
Speaker 1: off because the case was fixed. I was like in
Speaker 1: a state of shock because I had never known that.
Speaker 1: I had never you know, I had never realized that.
Speaker 1: You know, it was the first word people that in
Speaker 1: this case was fixed. I just know that he was
Speaker 1: killed as lum. According to Bob, these were among the
Speaker 1: very last words that his father ever said to him.
Speaker 1: It was like he was giving me a message. I
Speaker 1: can't tell you that the story about Bob's grandfather is
Speaker 1: entirely true. He was a cop and was killed on
Speaker 1: the job, and the alleged killer was acquitted. But the
Speaker 1: whole bit about the first word guys fixing this case, well,
Speaker 1: that's more like family legend. What does seem clear to
Speaker 1: me anyhow, is that Bob's dad was sending him a message,
Speaker 1: a final bit of fatherly advice. It was like, after
Speaker 1: all those years of going easy on Bob, of not
Speaker 1: disciplining him, his dad was finally putting his foot down,
Speaker 1: telling him what he really thought, What are you doing
Speaker 1: with these guys? And this raised a delica question for Bob.
Speaker 1: Could he escape because it didn't seem like the mob
Speaker 1: would let him go naked? The gangster had said it best.
Speaker 1: Bob was a lawyer, but he was like a mobster too,
Speaker 1: and you just can't quit next time. A Deep cover
Speaker 1: the world of Chicago Justice a buzz with scandal press
Speaker 1: leaks of a huge undercover investigation into bribery in the
Speaker 1: nation's largest and busiest court system. Deep is produced by
Speaker 1: Jacob Smith and Amy Gaines and edited by Karen Shakurgie.
Speaker 1: Our senior editor is Jan Guera. Original music in our
Speaker 1: theme was composed by Luise Gara and Fawn Williams as
Speaker 1: our engineer. Our art this season was drawn by Cheryl
Speaker 1: Cook and designed by Sean Karney. Mia Lobell is our
Speaker 1: executive producer. Special thanks to Heather Fain John Schnarz, Carl mcgliori,
Speaker 1: Maya Kaning, Christina Sullivan, Eric Sandler, Mary Beth Smith, Brant Haynes,
Speaker 1: Maggie Taylor, Nicolemrano, Megan Larson, Royston Baserve, Lucy Sullivan, Edith Russlo,
Speaker 1: Riley Sullivan, Jason Gambrell, Martin Gonzalez, and Jacob Weisberg. I'm
Speaker 1: Jake Halbern. Subscribe to Pushkin Plus and you can binge
Speaker 1: the rest of the season right now ads free. Find
Speaker 1: Pushkin Plus on the deep Cover show page in Apple
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Speaker 1: listen to podcasts.