May 1977. After a witness decides to speak out, a hitman named Harry Aleman stands trial for the murder of William Logan. Bob Cooley is asked to “handle it.” The case is make-or-break for Cooley’s career, and possibly his life.
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Pushkin Jake Alpern here before we get started, I wanted you to know that deep Cover Season two will be dropping weekly on Mondays, but the full season is available right now ad free for Pushkin Plus subscribers. That's all ten episodes right away. Fine Pushkin Plus on the deep Cover show page in Apple Podcasts, or at Pushkin dot Fm. Previously on deep Cover. By the mid nineteen seventies, Bob Cooley had earned a reputation in Chicago as a flashy criminal defense lawyer who knew how to win. Sometimes he won Fahren Square, but he was also willing to place a bribe to get the verdict he wanted. In nineteen seventy seven, Bob was approached by Pat Marcy, the mob's political czar. Marcy asked him to fix a murder case, something that Bob had never done before. And this wasn't just any murder case. It was the trial of a mob hitman named Harry Alaman. He's like a bantam rooster, looks like somebody who if you rubbed up against him, you sort of believe. Because he's the razor's edge. Bob knew that he needed to get this case into the hands of the exact right judge, and according to Bob, he had the perfect person in mind. Bob Cooley was a guy who seemed to know everyone when he wasn't in court. Bob liked to eat out, party, and gamble. Sometimes he mixed work with pleasure. He was an off the book silent partner of an Italian restaurant, a place called Grecos, where he schmoozed with lawyers, judges and clients, and sometimes he took the guys he really liked to Vegas. Bob gambled so much the casinos would often fly him and his friends out on a charter plane. Bob says he made one such trip in the mid seventies with a judge named Frank Wilson. I should tell you Judge Wilson is no longer alive, so I couldn't ask him about this trip or get his side of things. But according to Bob, he and the judge get out to Vegas, gamble, have a good time, part ways at some point, and then in the wee hours of the morning they reconnect. You're sitting at the bar and there's a girl sitting next to him, who I'm assuming as a working girl. Bob says that the judge had a bit too much to drink that night. So Bob and this quote working girl helped the judge back to his room. Afterwards, this woman goes back to Bob's room with him. Once there, she suggests that they take a shower before you know, so, I know, I get naked. I go in there. She's naked. When I go in there, I get in the shower. She doesn't get in the shower. Okay, I'm in there no more than three or four minutes. And now it hits me. I got about I don't know how much five to six seven thousand in cash in my pocket. I had just gotten a big fancy diamond ring not that long before. Suddenly I jump out of the shower. By the time I get out, she's already out the door, because I opened the door and I see her towards the elevator, and I'm naked, and I'm running. The moment I come out and she's gone. I know, damn well, what happened. And I opened the door and I see her, and as I say, I'm naked, but I go running after her. She gets in the elevator and down she goes. Wait seriously, Bob, honestly, you were running naked down the hallway. What did I just say? Bob frantically hits the down button. In hot pursuit. A new elevator arrives, Bob rushes in. I get in there, and there's an old couple, old couple standing in there. Like I said, it's about six in the morning. Now I just put my hands over my schmuck and I don't say a word. A woman, especially like as if she, if she could have pushed her way out the back of the elevator going down, she would have wait. Hold up, Just to be just to be totally clear, Bob, you're buck naked in the elevator, covering your private ports and there's an elderly couple corned over the other far end of the elevator. Not but the elevator wasn't that big. We're talking a small elevator, probably about three feet behind me. And I turned my back, and you know, but I'm covering. I'm covering my shug. But now I have to get out of there. And were at the ground level, so I run over to the poll and I grab a towel and I go see the security and I said, I just got robbed. I didn't know, but I assumed I got wrapped or she wouldn't have been, you know, gone. All my life, I've been able to instantaneously, you know, figure things that are happening. That's been my nature. Well maybe not instantaneously. I mean, she did get away, but you got to give Bob an a for effort. Eventually, Bob says, he checks in with the judge in the morning. I see Frank and Frank is complaining. You know, he had like eight nine hundred bucks in his pocket and she robbed him. He said, why'd you let her do that? Yeah? Why? He said? Why did you let her? Explain the name for him getting robbed? But I said, she got me for a lot more than she got you. The whole thing was like a scene right out of the Hangover. It was a classic what happens in Vegas stays in Vegas moment. Bob says that he did all this simply because he liked to have fun and he valued Frank Wilson as a friend. But all of this male bonding served another purpose. It built trust, something that Bob might use to his own advantage if he ever wanted to, which is why in early nineteen seventy seven, when Bob was asked to fix a high profile murder case. Bob thought of Judge Frank Wilson. Bob says he just knew this would be the judge to ask the man to take the bribe, and if it worked, if Bob could pull this off, he'd prove his worth to Pat Marcy and the Mob. He'd be the man in Chicago. I'm Jake Halburn and this is Deep Cover mob Land, Episode three. The fix Bob's relationship with Judge Wilson. It was complicated, and all we have is Bob's version of what it was like, which should be taken with a grain of salt, because look and stories, Bob tends to be the hero. With this in mind, I did some digging and tried to figure out exactly who Judge Wilson was. People who knew the judge well remember him as a no nonsense Irish guy, a World War Two vette who walked with a limp and had a reputation for being tough on the bench, a serious man. So he walked with a limp. Here's crabby, and he was very state minded. That's Bill Murphy. He worked as a public defender in Frank Wilson's courtroom. He also happened to go to college with Bob, so he actually knew both men pretty well. He says that in college, Bob was a wild man. I mean, I like Bob. He was a good wrestler. When he was at college, he was He's good in a fistfight, you know, I mean, he just was out of control. By contrast, Judge Wilson, or Frank as he calls him, was a play by the rules kind of guy. Lawyers would you know, come in to say hello to Frank. You know, it was pretty congenial. If there were certain lawyers that would come into his chambers, he would signal me to come in there too, being a witness that no hanky pinky was going to go on. Does that make sense to you? This made perfect sense to me. This was a city and a courthouse plagued by corruption, and Judge Wilson was taking precautions, protecting himself and making it clear that he was operating above board. Murphy says one time a lawyer tried to send Judge Wilson a referral fee. Apparently the judge had sent a client his way and lawyer wanted to show his thanks. Wilson flat out refused. Apparently, this lawyer was still determined to show his gratitude, so he sent a case of scotch to Judge Wilson's bailiff. You know the guy in the courtroom who says all rise. Judge Wilson put the kibosh on this too. He insisted that the bailiff returned the case of scotch. In fact, he asked Bill Murphy to help move the liquor because apparently the bailiff was an older guy and had a disability. Frank said to me, he said, we're not taking I'm not letting my bailiff take that. He can't carry it back to the lawyer's car. Would you do it? And I did. Murphy was also now a witness, someone who saw the judge had done the right thing and saw that the judge didn't want even a whiff of impropriety in his courtroom. Bill Murphy told me that's just who Frank Wilson was. An honest man. I didn't really have you know, illusions about him. He was a very tough father. You know. He wasn't telling me it was great all the time. It was kind of just the opposite. But in spite of all that, I really admired him. That's Frank's daughter, mary Anne Duncan. I don't know. He just really loved the law. He watched Perry Mason, like every single parent Mason about one hundred times. And when he became a judge, I don't think I've ever seen anyone happier in a job. Marianne says that her dad made a comfortable living as a judge. The family always had enough money because her dad was frugal, a no frills kind of guy. Like when they went on vacation, we would say like a Howard Johnson's, but then we would go have a drink or something at like the fancy hotel, but we'd be back at the more average place. So anyway, was never extravagant. She says that her father wasn't driven by money and would never take a bribe. Now you might be thinking, of course, isn't this what any daughter would say, But Marianne was adamant. I thought my father did anything wrong, I would admit it, you know, because it wouldn't be something I did, you know, it wouldn't be my fault. If he did something wrong. Marianne also disputes that her dad and Bob Cooley were even friends, and in a way, I can see why she says this. They seem kind of like opposites. But I can also see how Judge Wilson's honorable reputation would be attractive and quite useful to a guy like Bob Cooley, especially if he wanted to fix a murder case and make it all look perfectly legit. Bob says that he also chose Judge Wilson in part because he drank too much, and this was essentially his achilles heel. When I asked Marianne about this, she said her dad did have a drinking problem. He would drink to excess for a few weeks, then stop and go dry for a spell. The bottom line for Bob was he felt if he talked to the judge in just the right way, at just the right moment, the judge might agree to the bribe. I had no idea how I was going to approach until I walked up before him. I had no idea what I was going to say. I didn't like to prepare something. He was just gonna wing it. So here's what Bob says, happened. He had this restaurant, Grecos, and he knew that the judge liked to dine there. So Bob heads to Grecos one night, hoping to bump into the judge. Just so you can picture it, Grecos was a huge place, looked like a wine seller, adorned with ornamental trellises and vines, good home cooked food prepared by Italian ladies from the neighborhood. Anyway, Bob shows up and spots the judge sitting with some friends. He gets the judge's attention and brings him over to a secluded spot. Then, ever so casually, Bob says, Judge, somebody contacted me and wants me to handle a case. That was the word Bob always used in situations like this, handle a case. If he would have said to me anything, did he affect that I don't want to talk to you about it or whatever? You know, so be it and the conversation. But he said something that really struck me as bizarre. He said to Bob, you mean the Harry Alaman case. Bob was taken aback. It was as if the judge knew what Bob was going to ask before he even asked it. The judge then told Bob, they sojade me on that case. S o j that stands for substitution of judge in Illinois, if a case is assigned to a judge and for whatever reason, either side doesn't like that judge, they have a chance to veto him ask for another judge. So that's what Wilson was saying to Bob. He'd been so ojade blocked on this case. Turns out Harry Alimon's legal team had vetoed Wilson, and they've done this almost certainly because of Wilson's tough reputation. This was news to Bob, but Bob had a hunch that with the Mob's help, they could pull some strings and undo this, get the case in front of Wilson, in other words, a problem that could be solved. Bob just plays it cool. He doesn't say anything right away. Instead, he waits. A few nights later. According to Bob, he bumps into the judge again and brings up the whole matter once more, tells the judge what a weak case he thinks this is, and makes his pitch, so I can get the case to you, you know, will you take it not? Saying to fix it or anything else. And he said to me, you can't do it. And I said, well, I think we can notice how careful Bob is being. He's poking around looking for a soft spot, testing whether the judge would even consider this. And Bob says the judge isn't giving him a hard no, more like a maybe, which is all he needs. Now comes the full charm offensive. He invites the judge to dinner at his restaurant. Bob's laid out all the groundwork. Now it's just a matter of locking him in. About maybe fut halfway through dinner, the judge went to the bathroom. That's when I thought I will approach him. This would be the moment he may be thinking really in the bathroom, But as you'll come to see, this was Bob's go to place to have discreet conversations. Anyway, Bob says. They get to the bathroom and Bob slips his hand into his pocket and clutches a wad of cash twenty five hundred dollars. I just took it out, and I put my hand out, and he put his hand out and he took it, and he said, what's this for? And I said, judge, you know that's for you. I said, if I can't get the case to yousopiate and I walked out. It was a shrewd play. Bob knew perfectly well that once the judge accepted the money it was a done deal. He was corrupted. So for the time being, the judge appeared to be on board. Bob had promised him that he'd get him ten thousand total once he'd quitted Harry Alaman, so that was one problem solved. Not long after this, Bob got a call from a mobster he knew. He asked Bob to meet at a motel out by the airport. When Bob arrives, they head upstairs to an empty room. A few minutes later, there's a knock on the door and in walks Harry Elaman. Harry had stone cold eyes. He just did. He reminded me a lot of Pat Marcy. Pat Marcy was the same way, but Harry looked pure evil. Apparently there was no mistaking who or what this guy was. He looks like what he was. He looks like a mobith guy, short, in pretty good shape physically. All he's wore a suit. Never saw Harry without him in a suit. I wonder if he went swimming in a fucking suit. Technically, Bob wasn't representing Harry. Harry had a veteran trial lawyer who would be arguing the case in the courtroom. Bob was just the fixer. But apparently Harry wanted to talk with Bob directly about Judge Wilson. According to Bob, Harry was worried, worried about the judge's tough reputation, and you can understand why Harry might also be a little confused. First, his legal team had blocked this judge. Now they were wrangling to get into his courtroom, which was kind of weird. And apparently Harry wanted to make sure that everything was under control. And I said, look, I said yes, I said I would handle the case. And that's when he said, if there's a problem, you're going to have a problem. What does he mean by that, If there's a problem, you're going to have a problem, Like, what does that actually mean? It means that you're probably going to get killed? What I assume it means. Even so, Bob says he didn't worry. Everything was going as planned, and the case did end up in front of Wilson. It wasn't until the trial began that Bob started to panic. By the time that Harry Alaman went on trial for murder, it was already a full blown media spectacle. Harry showed up in court dressed to the nines with all the panash of a celebrity. He even looked a bit like a young al pacino, sporting a series of silk ties and perfectly tailored suits. The way the media described him, it was like the Grim Reaper had gone shopping at Barney's. Right off the bat, Harry's defense team tells the judge that they're giving up their right to a trial by jury. Now some defendants like juries see them as more sympathetic, which makes sense, unless, of course, you've bribed the judge. Then you want a bench trial because in a bench trial, well it's all up to the judge. With that matter settled, the trial begins. The first witness to be called to the stand was from the family of the victim, Billy Logan, his sister you know her as Aunt Betty. The famous Chicago columnist Mike Royko captured the scene. He described Harry's reaction as the Logan sisters testified about the death of their brother. He wrote, quote, Harry just sat there, looking as cool and impassive as he has throughout. If being unjustly accused is a nightmarish experience, he's holding up about as well as anyone could. Turns out, this cool and impassive appearance. It was very deliberate on Harry's part. It was a whole way of being, and Harry's family had to follow it. Frankie for Leano, his daughter, remembers this, well, if I don't care what they say to me, I don't care what they do to me. You are just show no emotion, get up and walk away from these reporters. Don't give anybody any satisfaction. Okay, let's talk about motive. This was a hole in the prosecution's case which they never really addressed in a satisfying way. There were reports in the press that Billy Logan may have been murdered because he refused to help the mob in a hijacking scheme. Now, if you recall, Billy was a teamster in theory. He had access to all kinds of information about trucks, when they arrived, when they departed, what they were carrying. The mob apparently wanted this info, Billy said no, and well he ended up dead because of it. That was one theory anyway. I say theory because Billy was dead so he couldn't talk, and the mob well didn't exactly have a pr guide to comment, so theory was all there was without a clear cut motive. The heart of the prosecution's case was the testimony of not one, but two witnesses to the crime. The first was Harry Alaman's accomplice, the driver of the getaway car, Louis Almeida, a childhood friend of Harry's. Louise testimony was pretty damning. Louis recalled the knight of the murder, how they'd driven over to Billy's house, how Harry had yelled out the car window to get Billy's attention and then shot him twice, he said, five or six seconds past, and then Harry shot Billy a third and final time. Louis said he started to speed away, but Harry told him, quote, drive slow, he's gone. It was a chilling account of a professional murder. The problem with Louis as a witness is that he was serving a ten year federal sentence on a weapon's charge. He was testifying, at least in part to get his sentence reduced. In the end, the whole trial really came down to the second witness, Robert Lowe. This is the guy who told Betty I saw it all, the guy who'd been out walking his dog when Billy Logan got shot. A guy who had absolutely nothing to gain and everything to lose by testifying, and you know it's the seventies. He was a young guy, very impressionable, and I think that did carry the day. That's Maurice Posley. He's a former Chicago journalist who wrote a book about Robert Lowe and this trial. It's called Everybody Pays. It really boiled down to Bob low and whether you believed Bob Lowe, and he was very believable. Basically, Poseley says that Robert Lowe is the star of the show. Everyone knew it from the moment Robert Lowe entered the courthouse, because he was surrounded by guards all with their guns drawn. It was like the President had arrived or something. And in a way it was no less momentous. Here was a regular guy, father of four, working stiff, don't forget dog owner who'd volunteered to take on the mob and thus far he had not been killed. That was like being in downtown Chicago and seeing Bigfoot with a red sox hat on Maurice Poseley. He points out, this didn't just happen. Robert Low didn't just wake up one morning, make a cup of foldiers, look in the mirror and say, you know what, I think I'm going to testify against that really scary hitman today. No, the prosecutors told Robert basically that he had a chance to do the impossible, put a mob hitman behind bars from murder. They laid it on thick, this was an opportunity that rarely came long for men such as them to actually get a conviction in these cases, and that this guy was the lynchpin, and so he became sort of, you know, their darling. You might say, we'll take care of you, will give you a new identity. You're going to have to change your life, you're going to have to move, but it's going to be an opportunity for you. And they impressed upon him his value to them, which was sort of not just a personal value, but it was a value to the society at large of what he was doing as a public service, but that's not all. In his book, Posley recounts a scene where Robert is told by prosecutors that he might be in danger. The subtext was clear, sign up with us, do your part, and you'll be safe. Do this for the good of your wife and your kids. So yeah, just a little bit of pressure. At the court house, he took the witness stand and began to recount what he'd seen that night. He had been taking his dog for a walk when he saw Billy Logan come out of his house. Robert began to cross the street so he could chat with Billy. Then a car pulled up. Robert testified that he heard a bang, and then he saw Logan's body fly back about four or five feet into some bushes. He then heard another bang. Moments later, the car door opened and an armed man emerged. Robert said his dog, Ginger, lunged at the man. He had to hold Ginger back. Then he made eye contact with the killer for four full seconds. Then came the most dramatic moment in the whole trial. The prosecutor said, mister Lowe, I'd like you to look around the courtroom and see if you can see that man in court today. That's when Robert raises his hand and points directly at Harry. The prosecutor then says, let the record indicate that the witness has identified the defendant Harry Alaman. Robert's wife, who was seated on a front row bench, heaved an audible sigh of relief. It was as if, after all of these weeks and months and years of living with this nightmare, maybe, just maybe it was finally over. During the cross examination, the defense did its best to poke holes in Robert's credibility and its testimony. They focused on inconsistencies in what he told the authorities, mainly small details like whether or not the getaway car had bucket seats. They said, in effect, his story at trial didn't match up exactly with what he'd told investigators previously. The defense attorney pressed on relentlessly. He questioned Robert's memory, hammering away in particular at the idea that he'd stared at the killer for a full four seconds. I'm going to read you a portion of his cross examination. Defense, how was this man dress that you stared at for four seconds? Robert, I was looking at his face? Defense, Well, it was a brightly lighted area. Was bright enough to see good, wasn't it, mister witness Robert, Yes, sir, Defense, And you can't tell the court what the man was wearing, Robert, I wasn't looking at anything but his face. Defense. Was he wearing a sweater? Robert I didn't notice. Defense. Was he wearing a coat? Robert I don't know, sir, Defense. Was he wearing a breaker? Robert, I don't know, sir, Defense. You want the court to believe that you stared at a man for four seconds and you can't tell him one thing as to his apparel. Prosecutor objection Judge. Judge overruled Robert. All I had in my mind on was his face. I'll never forget that face as long as I live. The good news for Robert was that most of his testimony was corroborated by other witnesses. His account matched up with what Louis Almeida, the accomplice, had described. It also matched up with what Aunt Bettie had said. At some point, there was a brief recess, and there was this moment captured by a local reporter. One of the victim's sisters approached Robert. Lowe's wife, grabbed her hand, then told her tearfully what your husband's doing. It can't bring Billy back, but maybe it'll stop them from doing this to anybody else. The scene made the papers. It seemed to capture the human drama that was unfolding here, a reunion of neighbors. Once upon a time they waved friendly hellos across the street, and now one family was risking everything so that the other might have a shot at justice. It was the kind of story that could make people care, see this is just not another mob murder, but a parable about courage and family and community. The newspapers covered each day's proceedings ravenously. It was a media circus, and at the center of this was Judge Frank Wilson. His daughter mary Anne told me that the press camped out on their front lawn, that they hounded her father with questions and her too. It was relentless. Everyone was angling for a clue. How would the judge rule? To local media in Chicago, the trial of Harry Alman was the gift that kept on giving. Every day offered new storylines that enticed readers and soul papers. I was still living with my mother and I was commuting on the train because I was on the south Side, and so every day I was reading the paper on the train and there was this trial going on day after day. This is Katherine Fleming, one of the many women who worked for Bob over the years. At the time of the trial, she was his trusted secretary, and well, I'll just let her explain their relationship. You know, he was nice, we liked each other, We worked together easily. There was an attraction. So yeah, it was easy. It was easy. It was easy, it was fun. Katherine dated Bob on and off for about twenty years and what was largely a commitment free relationship. They were very close, but she says she didn't know the ins and outs of how Bob operated. Yeah, I'm not sure. I really didn't know what he was doing. I was not part of any client meetings ever, so I had no sense of what he was or wasn't doing other than getting criminals off, for instance. Even though she was reading about the Harry Alaman trial every day on our way to work, she had no idea that Bob was involved in this case. He never let it slip, not at work, not in bed, not ever. Bob kept all of his dealings in this case very hush hush. The best thing he could do, in fact, was stay away from everyone involved. So he says he wasn't thrilled when during the thick of the trial he got a call from Judge Wilson himself. I get a phone call from the judge. He called me from a pay phone over there by twenty sixth Street. He calls and he says, you know, can I meet He wanted to meet me at the at a restaurant over on Ciero. According to Bob, he shows up at the restaurant, sees the judge and together they head off to yep, you guessed it, the bathroom. And he's like, he's like shaking, He's like all nervous. What's matter? And I said, Judge, you know, look, you know what what can I tell you? Now? I am nervous, you know, and there's nothing I can do about it. And I said, well, Judge, hey, you know what can I tell you if something goes wrong? I said, I've got a problem. And I had no idea what he would do now myself, because he might find him guilty. I mean, that's with making me nervous because it sounds like maybe he's gonna say forget about it. I don't know what he's going to do, Jake. I don't know what you're gonna do tomorrow. I don't know what he's gonna do. What would happen if he found him guilty? I'd probably wind up getting killed. Bob was a bit shaken, but he did his best to calm the judge down, assure him that everything would be all right. And it turns out Bob did have an idea how he might fix things or make them better. He says that at one point the judge it complained about how much money he was being paid, So Bob decided to go back to Pat Marcy and see if they could up the bribe offer more than just the ten thousand. So Bob paid a visit to Counselor's row and found Pat Marcy. The mob's politicals are the guy with the tinted glasses. We walked out into the hall and I said, he's a nervous wreck. Well he better doing you? I said, you should we offer him some more? Should we offer him some more? And he says he said he'd do it for ten. It better be done for ten. That saw not a nickel more that ratt and sib and that was it. There was nothing more that Bob could do. The trial drew to a close in late May of nineteen seventy seven. Bob, by his own admission, was a nervous wreck. So the night before the verdict was announced, Bob did well what Bob always liked to do. He hit the town kind of like a last hurrah. I went to my restaurant, I went to the nightclubs, a couple of nightclubs. I was out until about met maybe about three or four o'clock in the morning. I went home with one of my sweethearts. When we got up in the morning, I packed a couple of bags. That's when I said, well, just in case there's a problem, I'm getting the hell out of here, Bob says the next morning, he got on the highway and headed west. Had no idea where he was going, just away from Chicago, because he knew if the verdict was guilty, he'd be on the hook. Pat Marcy would hold him accountable. Meanwhile, back in Chicago, it was standing room only in the courtroom. It seemed like the whole city was hanging on the outcome. What would Judge Wilson do? Did he have enough reasonable doubt to acquit or would he send a hitman to jail for murder for the first time and as long as anyone could remember. The judge began his statement by issuing a stern warning. He said, quote, all right, ladies and gentlemen, it's now time for the finding by this court. When I announced my decision, I will not tolerate any outbursts by anybody in this courtroom. He then explained that in his tenure as a judge, he'd presided in over a thousand cases, some tough, some easy. He'd even sentenced two men to the electric chair. Although this case has created a certain amount of public interest, it is not a particularly difficult one, he told the courtroom. It all came down to the credibility of the two eye witnesses, he explained. The judge said he was required by law to view the accomplices testimony with suspicion because he was an accessory to the murder. The judge gave more credence to the testimony of Robert Lowe, but he wasn't entirely won over by it either. He pointed out some discrepancies between what Robert said on the stand and what he told investigators prior to that. The judge went on to say, quote, my job here is not to say whether the defendant is innocent, and I do not say at this time that he is innocent. That is between him and his God. That's the moment that made it into all the papers, the moment when everyone seemed to understand where exactly this was headed. Johannes and Tanello, the niece of the victim, remembers this moment vividly because I remember my mom squeezing my hand and she started to cry, and he said, how could this be? How could it be that he's saying this is between him and his God. I think everybody was just stunned and it wasn't making any sense. The judge continued, my decision may not be a popular one, but for those who disagree, I wish to state that every defendant, and I mean every defendant, no matter who he might be, is entitled to a fair trial. With all of this in mind, the judge concluded, I find the state has fallen far short of their burden of proving the defendant guilty beyond a reasonable doubt. There was an uproar for Harry's daughter, Frankie. There was no immediate joy or even relief. It was just like, I don't even know. I was just numb. That was just numb. My mom was next to me and just staying there, and my Mom's like, it's okay, It's gonna be okay. Harry eventually made his way out of the courtroom, walked away a freeman, all the while the news cameraman clicked away. It was an iconic moment. Here's Maurice Poseley, the journalist, the image of Harry walking out of the courthouse with his wife and attorney with a sort of smirk, self satisfied smirk on his face that gave you the impression of see, I could have told you that this was going to happen. Meanwhile, miles away in his car heading west, Bob Cooley was listening to the news I heard on the radio. You know, the judge found him not guilty. You know, everybody's screaming because the evidence was overwhelming and all the rest of that bullshit. I turned the car around, turned his car around because he'd done it. He'd gotten the verdict he'd wanted. He'd come through for Harry Alaman, and more importantly, for pat Marcy, the Mob's political czar, Bob had taken a huge risk. Even for a veteran gambler like Bob. This was an epic roll of the dice. As the city of Chicago came back into view and the recently completed Sears Tower loomed in the distance, it must have seemed like this city was his for the taking. But first there was something he had to do. He says, he had to pay off Judge Wilson, pay off the balance of what he owed, because he'd only given him twenty five hundred so far. They arranged to meet at a restaurant on this final meaning between the two of them. Bob says he decided to bring along his secretary slash lover, Catherine Fleming. He said he did it to lighten the mood, though he didn't tell Katherine why they were meeting up with the judge or even who he was. When they arrived at the restaurant, they spotted the judge. Bob says he looked terrible, like he'd aged fifteen years in the last two weeks. Katherine had a similar memory. He looked old, alcoholic, thin, drawn, sad, unhappy. They quickly parted ways with Catherine and looked for a place to talk. We walked into the bathroom. He turns around, he said, you've destroyed me. According to Bob, the judge told him that he was going to be crucified in the newspapers for this decision, that his days as a judge were effectively over. He told Bob, you did this to me. At some point, Bob says, he handed him an envelope with the money, but he didn't know what to say to the judge, Not really, I mean, what was there to say? Even smooth talking Bob Cooley was at a loss for words, and before he could figure it out, the judge just turned around and walked out the door. After leaving the bathroom, the judge sat down next to Katherine and he said something to her that she still remembers very clearly, even now, almost forty five years later. The judge looked at me and he said, you look like a nice girl. Stay away from him. He's bad. It was a very pointed remark. What do you make of that when he says it to you that he was having a problem with Bob. I just slipped him in the eye and let him know that I was listening to him. That's it, That's all you can do. Bob soon emerged from the bathroom. He glanced over saw the judge with Catherine, but he couldn't bring himself to join them. He says, he didn't want to be there, and so he walked past their table and just kept going. Next time on deep Cover, I said, if anybody thinks for one second, I'm gonna even take a beating, they're thinking wrong, I said. And if I think I got a problem with you, I said, You're gonna have the fucking problem. Deep Cover is produced by Jacob Smith and Amy Gaines and edited by Karen Shakurge. Our senior editor is Jan Guera. Original music in our theme was composed by Louise 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, Carli Mcgliori, Maya Kany, Christina Sullivan, Eric Sandler, Mary Beth Smith, Brant Haynes, Maggie Taylor, a Coolemarano, Megan Larson, Royston Beserve, Lucy Sullivan, Edith Russello, Riley Sullivan, Jason Gambrel, Martin Gonzalez, and Jacob Weisberg. I'm Jake Halbern. 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.