Episode 4: The Favorite Son

Previously on deep Cover. In nineteen eighty six, Bob Cooley, a Chicago lawyer who had worked for the mob, walked into the office of a federal prosecutor and offered to cooperate. Prosecutors were mystified why was he doing this? Up until this moment, Bob Cooley had a reputation as a flashy criminal defense lawyer who helped at least one person get away with murder. Literally. In nineteen seventy seven, Bob vixed the trial of Harry Alaman, a legendary mafia hit man.

The judge is not guilty. Verdict provoked outrage from both the media and the public. They couldn't even speak, that's how the man and how livid they were. They could not believe that this judge didn't fight him guilty. The place went into a piano, but for the mob. This case proved Bob's worth. He could be their ace in the hole. Not long ago, I called up this guy who used to know Bob. We're going to call him Nick. Nick is in his real name. It's just a nickname

that we're using to protect his identity. Bob Cooley was the best man. He was good at cooks and cases, and hey, they knew how good he was if. I always said, if I get some deep shit, it's going to be a Bob, and Nick was always on the edge of some deep shit. I was a captain and the mob not don't be waving my flag, but I was one of the smarter guys out there. My crew was known as the Enforcement Crew, and we we would go and do the dirty jobs that other people couldn't handle.

Back in the day, Nick's specialty was collecting unjuice loans. I asked him how he operated. What he'd do if I owed him money it didn't pay up. Nick says

he'd start by asking for it politely. But if that didn't work, well, I tell you, Jake, you know, if you got twenty four hours to come up with that money, if you don't come up the money, I'm gonna come bust your fucking head or pop your eyes out and gat him like grapes any and he'll lingo like that, any any kind of Sometimes you gotta grab the person by the throat. Sometimes you gotta grab you know, sometimes you gotta you know, knock him out to break their

lose all defense. What the scenario is, perhaps inevitably Nick or one of his guys would get in trouble with the cops. When that happened, he knew he could count on Bob. And the proof was the Harry Laman case. When you get a guy that's a hitman and you get him off of a major case, a murder case,

I mean, everybody's gonna say. Everybody says, hey, I get in trouble and going to Bob, which kind of makes you wonder how'd Bob become the kind of guy who'd do this anyway, who'd fix cases for the Mob and think you could get away with it. In this episode, we're going to take a hard look at how Bob became Bob and where it all started to go wrong for him. I'm Jake Halpern, and this is Deep Cover mob Land episode four. The favorite son Bob had taken

a big risk by getting involved with the Harry Lamon trial. First, he'd made a risky promise to Pat Marcy, the mob's political czar, that he could fix the case. He'd also assured Harry that all would go well, and he targeted a judge with an honorable reputation. The whole thing, start to finish was very bold, but somehow or another, it

all worked out for Bob and the outfit. Anyhow, according to Bob, Harry the hitman, essentially became his pr guy told him, listen, give me some of your cards, he said, because I got all kinds of business, I got all kinds of people. Now, he says, you're going to be the top lawyer in the city. Business was better than ever for Bob, but still he kept his guard up. Bob says he always assumed everyone he met was wearing a wire. This kind of paranoia kept him safe and

with new clients. Bob also avoided overpromising. He said, well, but can you guarantee something? I can't guarantee anything. I'll just do the best that I can. But his best was plenty good enough. I've got thousands of friends, I mean thousands of friends in the city of Chicago. Bob was living it up. I'm living a fantastic life. I've got all the friends in the world. I've got sweethearts

coming up and down and all around. Sometimes I got this sense from talking to Bob that being a lawyer for the Mob was all glamor that he lived a charmed life and look in many ways he did. According to Bob, unless he was trying a case, his workdays were generally over by midday. Then he'd grabbed lunch. Next he'd have a steam bath and then a massage. In the summer, he might hang out at his poolside cabana. Otherwise he'd go back to the office, head to the

conference room, where he'd play cards. Jim was his game. Then night he hit the clubs, or he fled to Vegas. One time even had dinner with Frank Sinatra and picked up the tab. This was Bob's life, but he was still a lawyer who needed an office in a filing cabinet and even a pencil sharpener, and he had this too. He shared a workspace downtown with a few other lawyers, including his brother Dennis Cooley. They actually use the same desk, sort of like a timeshare. Well, we were in the

same office. He had literally in the same room and would just use it sometimes he'd use it sometimes. Dennis was four years younger than Bob. He also started off as a police officer, then became a lawyer. But here their paths diverged sharply. Dennis went on to become a prosecutor, and a good one. At some point he ran an entire division. I talked to a bunch of people who knew Dennis from back then, and they all pretty much

said the same thing. Dennis was an honest and honorable guy. Eventually, Dennis decided to go into private practice, and like his brother, he became a criminal defense lawyer. But unlike Bob, Dennis was a clean criminal defense lawyer, which wasn't easy. He was practicing law in a system where so many of his competitors were guys who would place bribes. Of course, I resented it, Yes, he absolutely resented it. I resented the fact that I had to work hard from my

money and these other guys didn't. You know, when you're practicing law and you know you're a better attorney than the next guy, and yet the next guy seems to win. All these cases in front of these particular judges, and it's like, this is bullshit, but that's the way it was. Dennis says that he didn't know the full extent of Bob's shady dealings, but there were moments when he did get a sense for what his brother was up to.

You know, some of the people who would who would come in were not the kind of people I would normally end up with as a client. Some of them were, you know, outright scary looking. You know, I just kept I just kept the hell away from him. Did you ever pull Bob aside and say, like, what are you doing? Cut it out? I don't. That would have been a complete, total waste of time. I don't think he would have listened to me. Interestingly, there were things about Bob that

Dennis seemed to admire. He said that Bob was really good in front of a jury, that he really knew how to connect with the jurors win them over. I found believable. I mean, Bob could be very charming. He also says that Bob wasn't afraid to stand up to bullies. This was true when Bob was a kid. He was short. Back then, people called him shrimp, which drove him crazy. Dennis says, one time Bob got in a fight with this much bigger kid. He was so much different in

size than this big guy. He would literally have to jump up to hit him in the face, and he would do that, and he backed the big kid off. And that kind of left the compression with me. How aggressive he could be, you know, and how he wouldn't back off from certain challenges. It also seemed telling to me that Dennis found all of these reasons to admire Bob. Dennis was a guy who saw the best in others, even his shady brother. So there were the Coolie brothers,

Bob and Dennis sharing the exact Sam desk. It was a powerful image. They seemed to be symbolic of the two realms of the Chicago legal system, the clean and the dirty, operating side by side, morally opposed but hopelessly interconnected. And for me, it also raised the question how had these two brothers turned out so differently. The Coolies were known as a family of honest cops. Bob's parents were

devoutly religious, So what exactly happened with Bob. To really understand Bob Cooley, We're going to go deep into his relationship with his father. But I want to start by giving you a picture of what the Coolie family was like back when Bob was a kid. And to do this, I got to take you back to the nineteen forties. The family lived on the South side of Chicago in an Irish Catholic neighborhood. It was a good childhood. Actually we were nine kids, so you know, so that is

an experience in itself. That's Tim Cooley, another one of Bob's six brothers. He lives in Vermont now, and as I tried to make sense of Bob's childhood, he became my guide, my guru. Really. I am a massage therapist and a yoga teacher, two things which really really make me happy. I work at a gay run retreat center doing yoga and massage. There. It's a community that is about helping people grow, basically, helping people be the fullest

that they can be. Tim is Bob's younger brother, and he spent a lot of time reflecting on his child hood and the Coolie family. He told me that their father, Jim Coolie, was extremely pious. All the Coolie kids said this by the way that their dad made them pray together. Jim Cooley the dad actually went to a Catholic seminary and studied for the priesthood before deciding to become a cop and eventually a detective. And by all accounts, he was an honest policeman, never took a bribe and didn't

look for trouble. Well, because my father was a really gentleman. He was like the least macho man I've ever met in my life. To some degree, Yeah, he really was. He was. I mean, he had an Irish temper mind, you you know, so he would he would get angry at times or whatever. But he was very he was very mild. To be clear, Tim doesn't have any illusions about his father. He told me straight up his dad could be a racist. But for the most part, Tim says he has fond memories of growing up in the

coolie household. We never felt like we were without you know we, I mean, we were just sort of the same as everybody else. We thought we would have called ourselves middle class, I guess. On the other hand, Bob told me that his family grew up very poor. I never had clothes. I never had new clothes as I grew up. All my clothes were. You know, my mother would be over basically at the school, begging, begging for stuff because she had two you know, for the you know,

for the sake of the kids. And I was really angry for a long time being born into a family with all these kids. I really was. I was angry at God because so many of people I knew had so much more than me. The worst for Bob was when his mother took him shopping for groceries and scoured the shelves for dented cans so she could ask the clerk for a discount for a few pennies off. This mortified Bob, I asked him about this. There you have

Bob and me a nutshell. The difference is that I would admire my mother for that, whereas Bob cared more about how things looked or how things seemed to others. I would say than I did as a kid. Bob worked all kinds of jobs, but that pocket money only got him so far, and he was still angry and frustrated by what he didn't have. And that sort of explains on some level, his drive to be financially successful.

Whatever it took for him to get that. He was always driven on some level driven, and I guess you would say a bit of a troublemaker quite frankly. I mean he would be good at getting out of trouble by hook or by crook basically, but he was always sort of working an angle, and Bob admits to this. He describes his childhood as one long tale of rule breaking, cheating on tests, starting fights, skipping church. Let me tell you, when it came to the coolie household Santa did not

have to check his list twice. And given all of this, you might think that Bob's hero was well, Jesse James or John Dillinger or some other scoff Law. Nope. Interestingly, the one person that I always heard Bob speak of with almost unflagging admiration was actually his dad. He extolled his dad's virtues. I couldn't take when I was a kid growing up. I'd go in there and steal candy and stuff like that because I was hungry, and because you know, I couldn't. I have no money in my pockets.

My dad would never have done something like that. Did you feel any sense of guilt or any sense that you weren't living up to your dad's standards? No, no, not at all. Honestly, this surprised me, given how much he revered his dad. It seemed like maybe Bob would just have a little bit of a hard time looking his dad in the eye, or feel just a bit

cheapish about his transgressions. Nope, says Bob. There was one occasion, however, when Bob seemed to push his father too far, when he really tested the limits of their relationship, and as you're about to hear, it was a defining moment for Bob. It was a Sunday. Bob says he was about fourteen years old. He'd been out in the alleyway doing what kids did before cell phones, namely, throwing rocks. Bob ended

up breaking a neighbor's window. The neighbor walks over to Bob's house, talks to Bob's mom, tells her what happened. In a panic, Bob blames his brother Bill, says, Bill broke the window. This lie, It doesn't hold up. The neighbor points to Bob says he's the one who did this. Bob says his mother was furious, and she tells him, basically, your father will deal with you when he gets home from work. A little while later, dad arrives and his mom launches right into it. Jem, that's this is a

you know, he's out of control. This is thing going on too long? Time you give and that she tells him what happened. His dad is not happy. I mean here, he's come back from a long day of work, walking the streets and forcing the law, and he learns that his troublemaker's son has broken a window and then framed his brother. And mom is pissed. Something has to be done about this, so his dad escorts Bob to the bedroom.

We go in there, he gets his police stuff, there's old policeman stuff, and then he goes and he closes the door and he tells me, bend over the bed. I bend over the bed and he starts hitting the bed. Mind you, his dad is not actually whipping Bob. He's just pretending to whip him. And you could hear this thump, thump, thump, And I start hollering, pretending I've heard him, and I guess I'm I'm screaming real loud. You know. Oh my mother now thinks she's beating me half to death. I

guess she opens the door. I laugh now I didn't laugh. Then she opens the door and here he is, and here I am, and I look up and she goes ballistic. She goes ballistic because she's caught onto the ruse. And at this point she's not happy with Bob or her husband. What's the matter with you, that's why he's the way he is or whatever? And my dad got it so shook my dad up. He started hitting me with the belt. I got into the bed because I mean he was

like a madman for a minute. And when I come under the bed, he grabbed the bed with one hand, picked the bed up, started trying to hit me under the bed another couple of times. And I'm crying because I mean, it's it's it hurt, It really hurt. And then get in your room. I go in the room. H m hm, Wait, Bob, what got you? What? What got you so upset all of a sudden? What did that? What was that about? I just saw him coming in the room. I just saw him coming in the room.

He came in the room and he was crying, I mean, I mean crying and he comes over. H I'm I'm laying in the bed and he's on his knees apologized to debate for her doing what he is, and all the times that we talked, this is one of the

only times I heard Bob like this. Somehow he was shaken by this memory of his father, the good cop, the pious man, the almost priest who's been flummixed by his son's constant transgressions, the gentle dad who finally been pushed to the point of violence, and then, in a fit of shame, the distraught man who'd come back and

asked for his son's forgiveness. Remembering all this seemed to upset Bob horribly, and the pain it seemed to me, anyhow, was not in his father's disappointment, not in what his father had done to him, but in what he had done to his father, and the love his father still felt for him despite it all. I don't think, you know, I don't know of anybody who has a more interesting relationship with a father, probably than me, Because like I said, I did all the things I did as a kid.

You would think he would be, you know, I'd be I'd be the worse in his mind of the kids. And yet even though I'm always getting in trouble and doing all these things, he always treated me as his favorite in every way. You know, the fact he wouldn't discipline me, He didn't believe in laying a hand on me, things like that. It was an unbelievable relationship that I had. Did you think he was Do you think he was disappointed in you when you were up to no good? The fact is he was not. I mean, I was

still his favorite son in every way. I mean, what where can I say? Bob told me this repeatedly, that he was his dad's favorite son. This got me thinking about what kind of dad, Jim cool he was. So I asked Tim, My father loved all his sons, has loved all his children. He really did, but it was it wasn't a very demonstrative sort of love, you know. I mean he would he would tell each one of us,

you know, you're my favorite son. You know, you'd roll your eyes and you'd know, you would you know that he was meaning, he was meaning something to be you know, to be meaningful. I mean, he was basically saying I love you, but he had a hard time saying it. And here is yet another crucial difference between Bob and Tim. When Dad told Bob, you're my favorite son, Bob absolutely

believed him. Took the gesture at face value, almost like confirmation that despite everything he'd done, that he hadn't come up short in his father's eyes, that he still always had the blessing of the pious man. And for Bob, as far as I could tell, this seemed to be like a green light. As for their mom, Tim told me she was at a loss on how to raise Bob and hold him accountable. Bob was such a handful that she didn't know how to deal with it, and

I think she saw him getting away with stuff. And I think that has that kind of explains Bob on some level, is that he never really paid the consequences for his actions, which is why maybe he was willing to do actions that were really beyond the pale. Ultimately, when Tim told me this, I started to see it. Bob grew up in a home where he could flout the rules, and he came of age in a city where the rules meant even less. There was no accountability for Bob anywhere, no one he had to answer to,

except of course, the mob. Ever, since he was a kid, Bob had a rebellious streak. I guess he could say he had issues with authority, and that pretty much never changed. Even years later, when he was a grown man and a lawyer for the Mob, Bob was still throwing rocks and breaking windows, testing the limits. And I'm going to tell you a story about a situation Bob found himself in the real crossroads where he took it upon himself to challenge the Mob and its power, which he would

find out wasn't so wise. There'd be no fake spankings for this offense. So it's nineteen eighty one. Bob is representing a friend of his, a gangster who'd gotten in trouble with the law, a guy named Frank Rannella. And one day Bob hears from a prosecutor in the case who tells him, essentially, there's something you need to know about your client, Frank. He's been a government informant in the past. Bob understood immediately that this would be a

death sentence for Frank. The Mob would murder any insiders who cooperated with the FEDS. That was a hard and fast rule, But you know how Bob is with rules. And besides, for Bob, this whole thing just felt wrong in his gut. If somebody told me they were going to kill somebody, and I knew that they were going to do it. I would have found a way to warn them. That's just me. Bob says he decided to

help his friend and client escape. I drove right to Frank's house, and when I went upstairs to his apartment and I told him, he puts a gun on me. He thinks I'm initially he thinks I'm setting him up, and he says, I'm leaving now, and you're walking out in front of me. If they're out there, as Bob tells it, Frank walks outside, looks around and sees that no one is waiting for him, so he realizes this does not appear to be a setup, understands that Bob

was truly just trying to help him. Frank passed away over twenty years ago, so I couldn't talk to him and get his version of events, but I did track down his widow, Faye Ronella. She still remembers Bob's visit. He gives he had this air about him, a very arrogant above it all, so to speak. I just didn't care for him. After Bob arrived, Faye says that he and Frank went off to talk in private. I sat in the front room while Bob Cooley talked to Frank

in the bedroom. I wasn't a privy to their conversation. Frank later told Faye that he was in trouble. They're going to try and get me, is actually what he said at them, meaning the mob. I was assuming at the time, they're going to try and find a way to get me, put me out of the picture if I go to court. Frank told her he had to get out of town. She was devastated by the news. I mean, he was everything to me, even though he

told me it's the very beginning of our relationship. He says, I want you to know something from the get go. He says, I'm nothing but a fourteen tarrot bum, A fourteen carrot bum, gold on the outside, bum on the inside, like a warning to me, you get involved with me, this is what you're getting involved with. Okay. And now it was almost like Frank's prophecy had come true. Trouble had finally arrived at the doorstep of the fourteen carrot

bum as predicted. Luckily, with Bob's help, Frank had gotten away, but now Bob was on the hook. I went back and asked Nick the Gangster about this. He remembers when all of this happened, and he appreciated the enormity of what Bob had done, the risk he had taken. You do things like that, you're telling the guy that you're gonna he's gonna get whack. Well, you're giving him two avenues. If he's got money, he can run. If he doesn't have money, or even if he has money, he could

run run into the arms of the FBI. Meaning you've given him a chance to switch sides in order to save his own skin. And now he might talk, spill his guts. So what Bob had done, it was no small thing. There would be consequences. Would Bob have understood that when he did that? Yes, oh yeah, Bob knod he interwork, he said, a mob better than some of the Bob guys. So what's your sense for why Bob

did that? Loyalty? Well, Bob's a loyal guy. Bob wasn't didn't want anybody to get hurt, and Bob doing that he crossed the line big time. Bob understood this, and so he wasn't entirely surprised when shortly after this he got a tip that his own life was in danger, so Bob ran for it. I flew out of town, went through California. I was there for about a week, and I said to myself, you know enough of this. I can't you know, I can't live like this. I got to go back and I got to get it

straightened out. He flew back home and decided to drop in on one of the mob bosses, who he knew pretty well. It was a Wednesday, and this is important because Bob knew that this mob boss went to the same restaurant every Wednesday to meet with his guys, sat at the same big table right in front of a picture window. Bob says, he just shows up unannounced and motions for the boss to follow him to the bathroom. And here Bob makes the case for why he should

be allowed to live. I said I did nothing wrong. I said, Frank is my friend, he was your friend. He did nothing to hurt you people. He wasn't wearing a wire and you guys or anything. But I want you to know too that you know I did nothing wrong. I did what I thought was the right thing, and it didn't hurt you people in any way. I said, I'm back now. I'm here to stay. I said, if anybody thinks for one second, I'm gonna even take a beating,

I said. You know they're thinking wrong, I said, And if I think I got a problem with you, I said, you're going to have the fucking problem. And kind of amazingly this seemed to work. They let Bob be and I have to confess I found this really odd, kind of hard to believe. I mean, really, Bob makes his impassioned don't you dare kill me speech in the bathroom, offers his moral justification for what he's done, throws in a bit of tough talk, and all is forgiven. It

seemed well too easy. So I asked Nick the gangster about this. He had to keep on doing what he's doing because Bob was a fixer, and they knew he was a fixer. He says, Bob didn't really walk free. It was more like the mob had done a little risk assessment on Bob and decided it wasn't worth killing him for now. So as long as Bob kept being useful, as long as he kept fixing cases for the mob,

he was safe. But that meant he couldn't just walk away if he said I'm want to quit, I'm gonna walk away after everything he'd done or all the cases he fix, did he know in this knowledge he has, they were definitely killed. But Bob couldn't quit. Bob was a lawyer, but he was like a mobster to you just can't quit. So yeah, he was trapped, and it was a diabolically clever trap if you think about it. You got drawn into the mob by the allure of it,

all the money, the power, the glamor. But you did what you were told, and if you tried to assert yourself or follow your own code, you did so at your own peril, because then the trap tightened, and then you really had to do what you were told, or one day you ended up in the headlines dead, just

another mob hit. Throughout this time, In fact, throughout Bob's entire tenure as a lawyer for the mob, he says he never really discussed what he did with his mom or his dad, though there were moments when he got a sense for what his dad thought about the mob, like once Bob took his parents out to dinner at his restaurant, Greco's, and as it so happened, Pat Marcy was also there that night with one of his associates. If you remember, Marcy was the mob's political tsar, the

guy who asked Bob to fix the hitman trial. Anyway, as Marcy and his friend got up to leave, Bob says, his dad turned to him and said, son, I used to arrest those people. Bob wasn't sure what to make of this. His father's memory had started to go at that point, but even so, it was an unsettling thought that Bob might be in bed with his father's old enemies. Then sometime after this, Bob's father's health took a turn for the worse. Bob went to see him in the hospital.

His dad was in bed and looked very weak. I was there for about maybe fifteen twenty minutes, and I could see he was getting worse and worse. And that's when he suddenly looks at me and he he was like, you know, not that lucid for a period of time and he just looks up at me and he says, son, He says, son, why are you wasting your god given talents with these people? These people He didn't have to

specify who they were. It was almost like he was speaking in Bob's code, saying without saying, but Bob, he understood. He was talking about all the gangsters and corrupt politicians. He was talking about the mob writ large. He was asking Bob, what are you doing with these guys? And then his father said one more thing. He brought up a bit of family history that Bob knew very little about. It involved Bob's grandfather, who was also a cop and

had been killed on the job. He said, you realize that my father, the person who killed my father, got off because the case was fixed. I was like in a state of shock because I had never known that. I had never you know, I had never realized that. You know, it was the first word people that in this case was fixed. I just know that he was killed as lum. According to Bob, these were among the very last words that his father ever said to him.

It was like he was giving me a message. I can't tell you that the story about Bob's grandfather is entirely true. He was a cop and was killed on the job, and the alleged killer was acquitted. But the whole bit about the first word guys fixing this case, well, that's more like family legend. What does seem clear to me anyhow, is that Bob's dad was sending him a message,

a final bit of fatherly advice. It was like, after all those years of going easy on Bob, of not disciplining him, his dad was finally putting his foot down, telling him what he really thought, What are you doing with these guys? And this raised a delica question for Bob. Could he escape because it didn't seem like the mob would let him go naked? The gangster had said it best. Bob was a lawyer, but he was like a mobster too,

and you just can't quit next time. A Deep cover the world of Chicago Justice a buzz with scandal press leaks of a huge undercover investigation into bribery in the nation's largest and busiest court system. Deep is produced by Jacob Smith and Amy Gaines and edited by Karen Shakurgie. Our senior editor is Jan Guera. Original music in our theme was composed by Luise Gara and Fawn Williams as our engineer. Our art this season was drawn by Cheryl Cook and designed by Sean Karney. Mia Lobell is our

executive producer. Special thanks to Heather Fain John Schnarz, Carl mcgliori, Maya Kaning, Christina Sullivan, Eric Sandler, Mary Beth Smith, Brant Haynes, Maggie Taylor, Nicolemrano, Megan Larson, Royston Baserve, Lucy Sullivan, Edith Russlo, Riley Sullivan, Jason Gambrell, Martin Gonzalez, and Jacob Weisberg. I'm Jake Halbern. Subscribe to Pushkin Plus and you can binge the rest of the season right now ads free. Find Pushkin Plus on the deep Cover show page in Apple

Podcasts or at pushkin dot fm. To find more Pushkin podcasts, listen on the iHeartRadio app, Apple Podcasts, or wherever you listen to podcasts.