Episode 7: The Philosopher King ft. Michael Imperioli

Cooley reached a breaking point with the mob. He was working at case the old fashioned way, without bribing anyone, and then the mob came in and took control of things, insisted on paying off the judge and fixing the case. In this case, it was a powder keg. It involved a young man who brutally assaulted a female police officer. Bob represented the assailant, and when the verdict came in not guilty, there was an uproar. As I'm going to walk towards the door, they're grabbing me and screaming at

me and yelling you trader and stuff like that. And I know why they're saying it, because I'm an ex policeman, and you know, how could you represent somebody you know who did something like that Bob was finished with the mob, and shortly after this he walked into the office of a federal prosecutor and offered to switch sides. Bob was determined to nail the guys in the first ward, especially the top guy, Pat Marcy. He was tired of taking orders from him, doing his bidding and being part of

this corrupt system. Bob he wanted to tear it all down, and to do this he would have to wear a wire. He was like a kid, just ready to run out into the into the recess area because I can go do this now, I can go do that now, I can go do this now. And it's like no, that's Marie Dyson. She and Steve Bowen were Bob's handlers at the FBI, the carpool buddies. They appreciated how eager Bob was, but there were, you know, rules. After all, this was a serious covert operation. There had to be a system

to it. There had to be a process to it, because it was our policy not to just wire up somebody, let them run out there and have a great time and not know what they're doing and not be able to take any responsibility for that. We were responsible for Bob I think he thought he was just he could wire up and just start having conversations. Maurice says they made it clear to Bob it was going to be methodical, one target at a time, and Bob got it. He

felt the gravity of the situation. The moment I put the wire around the first time, my life was over. I couldn't never practice law anymore. I couldn't never stay in the city anymore. If it ever got out, they would kill me in a heartbeat. Period case closed, Bob began to take it as a given that his days were numbered. In other words, it wasn't a question of if he'd be outed as the mole, it was just a question of when, and so he had to prepare

for this eventuality. I thought they would eventually get suspicious or something would happen, but I thought I would be killed. I wanted to make sure that the case would survive, even with me Dad, if this was it was very important to me to get everything on tape, you know, that would survive me. Sure. Bob was scared to death. For Bob, it was all about tape, and he remembers telling Steve, I want the biggest tape recorder you've got the one with the most tape that can record the

most hours. Remember this is the eighties, back when tape was literally tape. They were still using old fashioned reel to real devices. And this is classic Bob right. Size matters, but size was also dangerous. The bigger the recorder, the harder it was to hide. Steve came up with a solution. Oh, I've went out and I'm boughting five hundred dollars cowboy boots and had pockets sewn in him. And then he got the wire running up his you know, up his pant leg and threw his crotch, and he didn't didn't

wasn't comfortable enough for him to wear. But so he wouldn't wear the cowboy boots. Why not? They weren't comfortable. He couldn't it, couldn't get it to fit right or something. I don't know. You can still hear a bit of confusion in Steve's voice, and I get it. Bob was full of contradictions. Here's a guy is willing to wear a recorder but won't wear the cowboy boots that would conceal it. A guy who thought he could be killed at any moment, but also insisted that he was ready

more than ready. I've been good at everything I've ever done. Anything, I've ever anything I've ever tried, I've been successful at I have been I tried wrestling, I was great at wrestling. I tried boxing. I was great at me. I was great at boxing. You have you have quite the ego, Bob, There's no question about it. I mean, if the facts speak for themselves, it seems like, and don't take this the wrong way, Bob, but you were kind of a cocky bastard. I mean, there's no question nobody else could

have done it. In my mind, there's no absolutely no question nobody else could have or would have. I'm Jake Halburn and this is Deep Cover mob Land, episode seven, the Philosopher King. In this episode, I'm going to tell you the story of three people who Bob targeted or betrayed, depending on how you look at it. The first was a mob boss, the second was a bookie, and the third was a poet. Let's start with one of the first guys. Bob wears a wire on John no Nos Defranzo.

Defronzo earned his nickname the Hard Way in his twenties. He attempted to rob a store, and police shot part of his nose off. By the nineteen eighties, when Bob knew him, he ran a Chrysler dealership, but really he was a high ranking mobster, a player in the Chicago outfit. Now, Defronzo was a good guy for Bob to start with, for a couple of reasons. One, it would demonstrate to the FEDS that Bob knew actual mobsters. And for Bob see he wanted to prove that he hadn't flipped because

he was in trouble with the mob. Around this time, Bob was down on his luck. He owed tens of thousands of dollars to some bookies in Chicago, but Bob claimed that Defronzo had basically waved his hand and forgiven these loans. Bob says, I can prove this, So he wires up and just waltzes over to Chrysler dealership and gets it on tape. Bob's handler, Steve Bowen, was impressed. I remember De Fronzo telling him in a really authoritative tone, no, Bob, I told you not to pay them, sort of like that,

like giving him an order. And with that, Bob was off to the races. Bob's next target was a bookie. He arranges to meet him at a restaurant. Bob uses an ace bandage to strap the recorder to his leg. Steve and Marie are stationed somewhere across the street doing surveillance. They'd given Bob cash to pay the bookie. I drive up to the restaurant. When I pull up, there in the front he's sitting on one of the stools looking out the window right at me. The bookie is already

in the restaurant, just staring out the window. The two men lock eyes. Bob then opens the car door and starts to get out. As they stepped out of the car, the wire I feel the wire falling out on my leg somehow as he swings his leg out of the car. This motion loosens the padding on the ace bandage. The tape recorder slips, and now it's just dangling from the wire. I can feel it. It was hanging down there under my shoe. Meanwhile, the bookie is still watching Bob through

the restaurant window. It's unclear if he's seen what's happened, but Bob needs to distract him and quickly, so Bob points across the street, hoping he can divert the Bookie's gaze like the oldest trick in the book. Look over there. Then Bob hops back in his car. I closed the door and I drove home, left him sitting in the window staring at me. And obviously the agents haven no idea what's going on. Bob speeds back to his apartment. He's trying not to panic, but he's spooked. What's going

through my head? Holy Christ? You know, I mean, this is it. My life is over and it's all within a couple of seconds. Bob gets home a little while later, Steve and Marie show up, and Bob says, Steve looks at him like, what the hell just happened? I said, you know the wire fell down in month. Did he see it? I said, I don't know. He's looking right at me. I said. I tried pulling it up, I said, but I don't know how he couldn't have seen me.

It appeared to be a full blown disaster, like they were just getting started and Bob's cover was already blown. Bob's handler, Marie remembers how distraught he was. He was a wreck. I mean he was just shaking because it was like I can't do this. I can't have this stuff happening. I'm gonna get killed. Oh yeah, and rightfully so. I mean he was that close to a guy noticing a wire on him. That's death, instant death. Bob's phone rang. It was the bookie. He also wanted to know what

the hell just happened. Why had Bob sped off? I said to him, did you see him over there? Did I see who? I said? I think there were undercover agents at the gas station across the street. I saw a couple of wouldn't look like unmarked cars. In effect, Bob is telling the bookie, I just did you a favor. You were being watched. That's why I sped away, and the bookie he buys it, and the proof is Bob Arrange is another meeting with the bookie and makes his payment.

Marie was impressed. He's good. There's no doubt about it. He's good. She wasn't entirely surprised either. He had seen too many people get killed and had heard about too many people getting killed because they made a mistake. Bob was not going to make that mistake. He had to be a resource, and one of the things he did well, No matter what came up, he always had some kind of answer for it. Bob may have been good, but the whole incident also reminded him of just how precarious

his situation was. At any moment. There were a million tiny variables that could come into play. The tightness of his ace bandage, the vantage point of the bookie and the restaurant window, a tremor in Bob's voice when he tried to explain himself. Any of these could have blown Bob's cover. Any of these could have gotten him killed. And given all of this, it seemed like just a matter of time before a disaster struck. As a lifelong gambler, Bob understood this only too well. You roll the dice

long enough, eventually you get snake eyes. When we come back after the break, Bob sets his sights on the first Ward, on a big target who happens to be a friend of his, or at least used to be. Bob's goal from the start was to take down the first Ward, the political machine run by gangsters. These were the guys who fixed cases and corrupted public officials. They'd been doing this for decades. I've been getting away with it too. They were savvy, and discreet. But they did

have a weakness, and it was a simple one. They trusted Bob with their secrets, and this place Bob in an interesting situation. It forced him to decide whom he would or wouldn't betray. Bob knew that once he told the FBI the name of a potential target, someone he could incriminate, well, then the FBI might ask him to do it. He thought about it and eventually decided, Yeah, he'd be transparent and give up the names, well almost all of them, because there were certain people. To this day,

I've never discussed with anybody and never would. What was your litmus test? What was your decider for whether or not you would name a certain person, how corrupt they were, and what they would or wouldn't do. I made my own decision on that. You decided based on your opinion of how egregious they behaved. That would be the decidre of whether absolutely it's odd you're almost playing the role of judge there. Yes, others I'd look him from the outside,

might think that's wrong. I could care less what they think. A more cynical take on kind of who you would talk about or not would be, Oh, people that Bob liked, he didn't hand over people who didn't like he handed over. Well, that's absolutely true. But the reason I liked or didn't like him was because of what the kind of people they were. With the two mob guys that he'd worn a wire on, Defranzo and the Bookie. This decision appears

to have been relatively easy for Bob. As he saw it, they were textbook criminals, and it might add guys that Bob wasn't especially close with, But it wasn't always quite so easy. There were other targets that Bob was much closer with, Guys he'd known for years, knew their families, Guys like Johnny Diarco Junior, a State Senator. As far as targets went, he was a pretty good sized fish. Johnny was majority whip in the States Senate. He wielded real power and influence, and in the end Bob did

hand him over to the Feds. But to understand why, let me tell you a little story. Because Bob's relationship with John Junior, or Johnny as he was also known, well, it was special. Bob and Johnny first cross pats in college. Bob says they started off his rivals even got into a fistfight. Eventually they became friends, even though they were really different guys. Johnny's whole world was Johnny Johnnies. The whole world was playing racquet ball, eating nuts and whatever.

Do you mean eating nuts and whatever? He ate nothing but nuts for a long period of time, nothing but I mean peanuts and whatever, because he believed he had some wackle. He was in the yoga and all this stuff like that. Bob was an irishman from a family of cops. Johnny was an Italian guy from a family with mob ties. Johnny grew up in the little Italy neighborhood of Chicago. His father, John Diarco Senior, had been a city alderman and was part of the First Ward.

Senior was a mob guy, and he looked the part. He wore fancy suits, smoked fat cigars, wore diamond pinky ring and like all good mob guys, knew how to keep his mouth shut. His son, Johnny Junior, couldn't have been more different. He was a fitness buff who read philosophy and wrote poetry. He lived in his own world. He was doing all kinds of poetry all the time. But I never asked him what it was. I didn't care. You know, I'd see him sitting there, you know, writing

all this stuff out. Johnny's interest in poetry wasn't just a hobby or a passing phase as a young man. That's what he really wanted to be. Not a politician or a gangster or a lawyer, but a scribbler of verse. Johnny Junior wouldn't talk to me for this podcast, but I did find a lengthy and excellent profile of him in the Chicago Tribune from the nineteen eighties up to then. I was an iron Rand type, all cool and rational.

That's the actor Michael Imperioli. We asked him to read Johnny's lines from that interview exactly as they appeared in print. In this article, Johnny talked about how in college he underwent a spiritual transformation. Then one day I asked myself the most fundamental question of all, Who am I and where am I going? He says that question led him on a journey of sorts. He became a long haired bohemian, and when he returned home from college with this new persona,

his parents weren't exactly happy. My father's attitude was it's a phase. He'll outgrow it. But mother must have called every relative on the phone asking them where she'd gone wrong. Johnny tried to explain his love of poetry to his father. I went to my father and said, man cannot choose to be. He simply is, and if he is, when is he not? Even after death, he remains matter. John Senior was understandably a bit puzzled by this. He asked

his son, what the heck was he talking about. Johnny replied, that is my poetry, Dad. He then offered his father a manuscript of his poems. A week later, my dad called me into his office and threw the manuscripts back across the desk at me. You're wasting your time with this stuff. I'd give it to a guy to read, and he says, it's no damn good ouch. No one likes getting a one star review from their own dad. Inevitably, it was tense between Junior and Senior for a while,

but eventually the poet came around. A friend of Johnny's told me that he realized poetry it doesn't pay the bills. So Johnny he cut his hair, put on a suit, and became a lawyer. It was around this time that John reconnected with Bob Cooley. In fact, Bob says it was John Senior who orchestrated this reunion. According to Bob, Senior basically pulled him aside and asked him to mentor his son. Here's how Bob remembers that encounter with Senior.

He said, I hear you're a terrific lawyer, and you know Okay, well yeah, I said, I'm not going to disagree with you. And he said, you know, my son John, I wonder if you'd take him under your wing and try to teach him how to practice law. Bob initially said, let me think about it, but eventually agreed to take him on. And just for context, this all happened in the mid nineteen seventies, very early in Bob's career. At that point, he had no real connections with the first Ward.

Bob was just a young lawyer, but he knew that this was a real opportunity to cozy up with some important players. What I thought about was what I could do, the powers I would have if I got connected with these people. Wait, just to be clear here, Bob, you're saying that this chance to be a mentor to Johnny Junior was an opportunity for you because it would get you in with these first ward guys. Oh sure, to get me into politics and to get me into you know,

into doing you know, magical things. Magical things almost like a gritty version of a kid's fairy tale. Helped my wayward son, and I will bestow great fortune upon you. That's kind of how Bob tells it. Anyway, So Bob agreed to mentor Johnny, and after a short period of time, I gave up trying to teach him how to practice law. He had no interest in learning how to do the right things or how to cross examine. Even so, they kept working together. Senior gave the venture his blessing and

welcome Bob into their home. John's mother used to cook for John and Bob Cooley. You know, they fed him, They treated him like a family member. That's Rico Paioni. He was a close friend of John Juniors and for a while he also worked for him. Rico told me he actually doubts that John Senior ever asked Bob to mentor his son. He thinks instead Bob wormed his way into the family's good graces, and that he wasn't acting

in good faith. And he knew what John's capabilities were, and as he knew the connections that he had, and so he went to him so he could take advantage of those connects. So he'd befriended John, and John, you know, took him at face value. You know, he didn't know he was going to specstab Um later on. Bob Cooley was an opportunist. He's still an opportunist. Bob flipped in nineteen eighty six. This was about a decade after he first started working with Johnny, and at that point the

two of them were no longer partners. Johnny didn't need any more mentoring. By then, he was a big man in Chicago. He was now a prominent state senator, and he'd even realize his dreams of becoming a published poet. Johnny put out a compilation of his poem called The Product of My Thought. Johnny embraced his role as a literary figure. When he was interviewed for that profile in the Chicago Tribune, he told the reporter, if people want to be more than passive acceptors of life, they have

to know something about philosophy. Sure, let him read some Hume. Maybe a little Kant, But if they really want to know where it's at, they're also going to have to read di Arco. Yes, you heard him right. Maybe he was joking, but he really did just place himself in the pantheon alongside Emmanuel Kant and David Hume, the two great philosophers of the Enlightenment. A bit bold, but in a tacit nod of approval. The reporter for the Chicago

Tribune dubbed Junior a quote philosopher King. When the book came out, there was a big party for Johnny. It was hosted by the owner of Chicago bookstore. The mayor of Chicago, Harold Washington, showed up, as did Nobel laureate Saul Bellow. The owner of the bookstore told the Chicago Tribune that Johnny's intellectual sincerity overshadowed his literary limitations. He said Johnny was quote patently one of those noble failures, like a Socrates or Jesus. The bookseller apparently asked Saul

Bellow what he thought of Johnny's poetry. Bellow replied, good, bad, what's the difference. The most difficult thing for a human being is to knock on silence. Here's an excerpt from one of the poems in Johnny's book. Let us suppose that everyone is sleeping at the same moment, Then if reality is consciousness, the world would not exist. But even if everyone is sleeping at the same moment, the world would still exist. But who is to say the world

is existing when everyone is sleeping. In the Chicago Tribune profile, the reporter asked Johnny what really motivated him as a poet. Johnny replied, I don't know, but something inside of me is always making me want to grab people and say, hey, I got a hold of the truth, you want a piece of it. The truth, however, was that Johnny was an operator. That's what Bob Cooley claimed. Anyway. He believed that Johnny was, in essence an extension of the First

Ward's dirty political machinery. Bob told his handlers at the FBI that in the past, on at least one occasion, Johnny had said, for the right price, he could push a bill through the state legislature. In short, laws for sale. I asked Bob what ultimately prompted him to hand Johnny over to the Feds. Of course, Bob had his litmus test how corrupt a person was and whether or not Bob liked that person. So I asked him, wasn't Junior

your friend? Well? I thought it was a friendship initially because of the way he acted towards me, and whatever. I thought it was a friendship, things happened that made me think otherwise. Bob says that he came to feel that Johnny was, in the end only interested in himself, that he didn't take being a lawyer seriously, and that

he lacked his father's discretion. Honestly, I just got the sense that on some level, litmus tests be damned, Johnny just rubbed Bob the wrong way, and that Johnny's value as a target was just too high to be overlooked. After all, he was a state senator who hailed from the first ward. So in the end, Bob wired up Hello, Hi Johnny, Hi brow are you what's up? This is an actual wire tap from a phone call between Bob and Johnny Diarco Junior. It was not easy to get

a hold of this, let me tell you. I mean, it's been over thirty years since this conversation took place. I figured these tapes had been lost or discarded, but with some help from the District Court for the Northern District of Illinois. We track them down at a federal storage facility. There they were like a time capsule that

had been forgotten and rediscovered. What the Bears did? They hunt got rid of McMahon, They started playing Well, Bob starts off shooting the shit about football and then quickly segues to this, Anyhow, I think I'm going to be in business with that situation we talked about. Okay, I talked to somebody yesterday and again the day before, and they want to go and check with the main people I guess or out in the ark. Yeah, and if they want to do something, I'll let you know. Okay,

I think it looks pretty good right now. All right, that sounds stuff. What I want you to notice here is just how vague and bland this whole conversation is Bob's is I think I'm gonna be in business with that situation we talked about. He's speaking in code back when he was a fixer, before he started working for the FEDS. This is how he talked to protect himself

in case someone was eavesdropping. Now that Bob was working for the FBI, he had to keep up appearances, so as he can see, Bob isn't trying to nail Johnny on the phone right off the bat. No, he didn't want to risk spooking him. Instead, Bob made a series of secret recordings over the course of a year. In phone calls, driving around town and at a ton of breakfast meetings. Bob would often wire up and go with Johnny to a diner. Okay, so there's a whole rhythm

to their outing. There's a booth where they like to sit. Today it's occupied. Bob tells the waitress somebody's glad table, sweetheart. They sit down, and when they do, Bob starts bantering with the waitress. He wants coffee. I think, did you see the advertisement for Pepsi though? Did you got Pepsi here? They got a new deal going nowhe They're gonna have a new Pepsi for breakfast. We have Okay, I drink cooke anyhow, But I can be an advertisement for him

Pepsi breakfast. That's Johnny by the way, saying Pepsi for breakfast. Really. Yeah, they got a new deal now. Pepsi's going to come out with something to do and encourage people start of having coffee to have their PEPSI. Bob's kind of being a goofball, just joking around, and then nonchalantly gets down to business. Starts enticing Johnny, hinting about some guys he knows with deep pockets. See, these people are good source

of business. You know, these guys are a big, big money in peopone and I made good money on the guy before. Then the waitress returns and Bob's back to being the jokester. The waitress asks them what they want to order. Bob points at Junior and says, this guy's got money. He doesn't care about what it costs. He doesn't look He's not looking for a Bargain's all that is. The waitress says she doesn't know Johnny is. Johnny says, don't tell her. All of this, by the way, is

part of Bob's strategy. That was all part of my schmoo with people, part of your what my scho schmick would have smuck whatever you want to call it, smooze. You know where you're where, you're just bs and people and they they what's the term they use where you're smoozing smoozing somebody? Yeah, not you're schmuck. That's something different, that's something else. We don't want to talk about that. I actually sat down with Bob and played this tape from the diner for him. I asked him, what was

the deal with the whole Pepsi stick anyway? You know, I always would try to approach him like I had in the past, and you know, and my attitude on most everything was really never too serious all my life. I told you, I never took anything serious in my life. I never did even when I'm even when I'm doing this, you'll make the most of it. Is this like, are you genuinely having fun here? I'm trying to because you've got to understand, as far as I'm concerned, I'm a

dead man right now. That's my attitude, and I'm going to live. I'm going to live every minute for the you know, for the moment. So Bob just kept going with his schmoo and gathering evidence against Johnny. A few months later, Bob has another conversation with Johnny. In this chat, Bob's trying to explain that he has a client who's willing to pay to get a law passed. Bob says it's a company that sells travel insurance. To sell insurance in the state of all, you've got to be licensed

as an agent. That some of these, uh you know, some of these the travel agencies are what already can sell some forms of nonsensical insurance. This is another type that the other companies just don't have. The other agencies just don't have this type of travel insurance. He says, some companies are already selling forms of quote nonsensical insurance. Then he says, basically his client has something similar, which he calls travel interruption insurance, and they need special permission

to sell it. Honestly, I found this all a little bit absurd and hard to follow, so I played it back for Bob, hoping that he could explain what the hell he was talking about. No, because I'm making all this up as I go along. I'm just making it up as I go along with him. There was no travel insurance company, there is no travel interruption policy. All of it was just a scheme. Does it even make sense to you now hearing it back? No, all that mattered is that he took the bribe and he's willing

to do it. The strategy was kind of brilliant. It was like one of those endless car rental agreements where the fine print just goes on for pages and pages so long that your eyes glaze over, and finally you say, fuck it, tell me where to sign. I Steve Bowen about this Bob's handler at the FBI, and he said all that mattered to a guy like Johnny was the bottom line, how much he stood to make. That's all he wants to hear. He wants to hear, what is it you want, and this is what it's going to

cost you. The detail is insignificant. They don't he could care less. You probably wouldn't have understood it anyhow well, it's I have to I listened to those tapes a few times. I can't really understand what Bobs we're not supposed to. That's the whole key to it. All he saw it was an opportunity to make good money. In the end, it didn't matter what the bogus law said.

It didn't even matter if the law passed. The point was Johnny, an elected official, was being paid money to use his power as a state senator to enrich a private company. A bribe was a bribe. All that Bob needed Johnny to do was accept the payoff, and he did. Johnny met with Bob in his car. Bob counted out fifty one hundred dollar bills, five thousand bucks total. Johnny took it, and so sealed the fate of the Philosopher King.

Bob was racking up some winds Defranzo the Bookie, the Philosopher King, but he knew that to accomplish his mission and really destroy the First Ward completely, he'd have to take down Pat Marcy, the top man, the guy with the tinted glasses, who had told Bob you just do what you're told. Bob understood the stakes. He knew that Marcy and his crew didn't mess around. These are killers. Marcy and these people are fucking killers. And as it

turns out, Bob was right to worry. Next time and deep Cover, Bob was never authorized to carry a gun under any conditions. Did I know on occasion that he had a gun on him? Yeah? And did I do anything about it? No. If I was going in to do what we're asking him to go in to do, I'd want a gun on me too. Deep Cover is produced by Jacob Smith and Amy Gaines and edited by Karen Shakerjee. Our Senior editor is Jan Guera. Original music and our theme was composed by Luis Gara and Fawn

Williams is our engineer, voice acting by Michael Imperioli. Our artason was drawn by Cheryl Cook and designed by Sean Carney. Mia lobell as our executive producer. Special thanks to Heather Faine, John Schnars, Carli mcgliori, Mayakining, Christina Sullivan, Eric Sandler, Mary beck Smith, Brant Haynes, Maggie Taylor, Nicolemarano, Megan Larson, Royston Baserve, Lucy Sullivan, Edith Russolo, Riley Sullivan, Jason Gambrel, Martin Gonzalez,

and Jacob Weisberg. I'm Jake Halpert. Subscribe to Pushkin Plus and you can binge the rest of the season right now. Adds 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.