Episode 5: The Babe in the Woods

I mean, he was good at pukskin cases, and they knew how good he was, and he was the fixture he was to be with the guy. By the early nineteen eighties, Cooley had established himself as mister Fixett, a guy the mob called if one of their own was in trouble, and Bob was also learning that working for the mob came with rules, but sometimes Bob broke them. I said, if anybody thinks for one second, I'm gonna

even take up beating. I said, you know they're thinking wrong, I said, And if I think I got a problem with you, who I said, You're going to have the fucking problem. And eventually they would have a problem with Bob, a very big one, but for the time being, Bob was still their guy. In the nineteen eighties, Chicago was corruption city, USA. Corruption was so insidious that over time some people stopped thinking about bribery itself as even being wrong.

It was kind of like a stop sign that fades and rusts and gradually gets ignored until no one even thinks about slowing down at the intersection anymore. No one, that is, except for this guy. I believed in God, motherhood in the flag and thought crime and corruption could be dealt with. This is mort Friedman. He's in his eighties now and long retired, but back in his heyday, he was a prosecutor at the Cook County States Attorney's Office. I doubt if anyone ever entered that office more naive

than I was. I thought I could do good. I thought I could help clean up crime. I thought I could make the streets safe for women and little children. And I went in there just a babe in the woods, absolute babe in the woods. His job was basically prosecuting criminals for a range of misdeeds, anything from theft to murder. Morton never tried a case against Bob, but he easily could have. They were cogs in the same machine grinding away. Mort says he remembers his early days as a prosecutor

very fondly. Oh, it was wonderful. I had a courtroom with a judge who was soft spoken, polite. I was doing exceptionally while as a trial lawyer. And yet it wasn't all perfect. There was this one defense lawyer that Mort kept on going up against. I knew I was going to lose. It didn't matter how well I prepared the witnesses, how well I argued emotion I knew I was going to lose. Mort began to suspect the judge was being paid off. After all, this was Chicago, and

this particular defense lawyer allegedly had mob ties. Even so, More kept trying his best to win. And then one day after work he had this epiphany. I was alone in the courtroom. It was a way past quitting time. I was preparing for the next day, and it suddenly dawned on me and I stood there thinking, I'm a pimp. The better I prepare, the harder I try. All I can do is drive up the price of the bribe to the judge. And it was a heartbreaking and devastating thought.

A realization it was just heartbreaking. Mort couldn't stomach it any longer, and apparently his frustration showed, because shortly after this, the judge leaned over the dais and looked at me and said, Mart, you've been acting surly lately. I don't think I care for your attitude. And I said to him, well, Judged, I don't care for the way you jump all over me. When this lawyer walks into the courtroom, I named him. The judge, quiet and soft spoken as ever, said Mort,

I think you ought to get another courtroom. I said, Judge, I think you're right, and put my files down and walked out. Corruption City, USA be damned. Mort was going to try to change the system, So get ready. In this episode, I'm going to tell you the story of the crusaders who tried to end corruption in Chicago years before Bob ever tried. It was a massive undertaking. The

FBI eventually got involved, marshaling hundreds of agents. They were going to war, and in a way, this all set the stage for Bob to make the most important decision of his life to switch sides. I'm Jake Halbern and is deep Cover mob Land. Episode five, The Babe in the woods. In the Hollywood version of this story, when Mort Friedman squared off with that judge in the courtroom, you'd hear the inspirational music and then you'd seem Mort hatching his plan to change the world. But it didn't

happen like that. Instead, Mort just switched courtrooms, kept trying to do his best as a prosecutor, to win the cases he could and to be honorable in a system that he knew was fundamentally corrupt. I was absolutely convinced at that point, did you share this with anyone, like even your wife? Did you shared this with anyone? With no one? Why is that a certain cowardice on my part, need to keep a job and not wanting to rock

the boat, not wanting to be an outcast. The trial courts at that point were a white Christian enclave, and there were one or two other assistants who didn't care for this jew on the floor. Mort says he overheard a few colleagues make anti Semitic remarks. As he saw it, this only added his sense that he shouldn't rock the boat and make enemies. Even so, I asked him if his decision to stay quiet left him feeling guilty or worse yet complicit. Certainly. In fact, I still feel that way.

There were things I could have done much better. In this way, Mort is kind of the opposite of Bob Cooley, constitutionally incapable of giving himself a pass. Mort eventually became the chief of the Criminal Division for Cook County. By population, Cook County is the biggest in Illinois and the second biggest in the United States. Mort oversaw the prosecution of thousands of felonies and misdemeanors each year. It was a

huge job. Then one day in nineteen seventy three, Mort was hard at work at his desk when a young police officer appeared silently in his doorway, waiting to be noticed. And when I looked up, he said, mister Friedman, my supervisor ordered me to come here. I've been offered a bribe to flippercase. The CoP's name was Jose Martinez. He looked young and a bit nervous. Standing in the doorway, he gave Mort the lowdown. The case at hand involved

an assault charge. Officer. Martinez was the cop who showed up on the scene and made the arrest. Now the defense attorney was asking him to pull some chinne nigans and helped make the case go away so his client, the assaulter, could get off. After hearing all this, Mort told the cop officer, I want you to do what you're told to do, and say what you're told to say, and bring me back the money. That's right. Mort told the cop to take the bribe. Officer Martinez, to his credit,

pushed back. He said, mister Friedman, I can't do that. I'd be lying in court. Mort was kind of amazed that the cop stood his ground. No, not just amazed, he was secretly delighted. Here's a young Chicago cop telling the chief of the criminal Division, I don't care what you say. I'm not going to lie in court. Looking back, Mort says he should have congratulated Martinez for wanting to do the right thing. But that's not what I did. Wait,

what did you do? In a conversation that was very loud and replete with upset of these, I told him what I would do to him and his career if he defied me. Why did you do that? I had handed up to my eyeballs with corruption. I knew something had to be done. See. Mort had a plan right there on the spot. Totally spontaneously. He'd come up with an idea for a sting operation. It was both inspired and a bit reckless. Mort didn't bother to get permission,

didn't map out all the possible consequences. He just wanted to do something, damn it, even if he had to put Officer Martinez in a very uncomfortable situation. Did you have any sense that maybe you'd opened to Pandora's box or started something that might end up being a big deal. I didn't care. It didn't matter at all to me at that point. I wasn't going to be a kemp. Now for his plan to work, he needed Officer Martinez

Is to take the money and lie in court. That way, the government could prosecute the lawyer who made the payoff. Did Officer Martinez understand what your game plan was? Did he understand that you were out to catch corruption or did he think that you were corrupt yourself? I don't know. I mean, in retrospect, I shouldn't have done that. I

should have just patiently explained to him what I wanted done. Eventually, Officer Martinez figures out what mord Is up to, so he plays a long lies in court and instructed, and then afterwards, when he goes to collect his bribe, he wears a wire and the result was a tape recording a dead bank crime on tape, a deadbang crime on tape. Bingo. Right, Mark went up for the good guys, only not really. The dirty defense lawyer was convicted of bribery. But more

strategy backfired. And let me explain why Mort was in effect tampering with the justice system. He was affecting the outcome of a real, live case. The irony, of course, was that this happened all the time anyway in a corrupt system. But the fact remained that Mort was breaking the law. He pushed a cop to accept a bribe in a single case in an attempt to stop bribery in general. The powers that be noticed what Mort had done, and now they set out to make an example of him.

It was just, you don't do things like this to lawyers. It's not nice. And besides, Friedman, you're allowing you're really a much bigger center than they because you allowed a police officer to lie. Mort was ordered to appear before the Disciplinary Commission of the Illinois Supreme Court. They said he was quote guilty of conduct tending to bring the legal profession into disrepute. For someone like Mort, this was a blow. I was mostly sad at the fact that

I had thought I had failed. Why do you think you cared so much? If you knew her, you were right. I don't know. I don't know the answer to that question. It was just like, this is insane, this is a circus, and I'm in the middle of it. And as for the circus, well, the show went on. By the time Mort was chastised by the court for his actions, Bob Cooley had fixed the big murder trial for Harry Alaman.

He was already well on his way to being the mob's go to guy, and the lesson from the Babe in the Woods seemed to be, Yes, the system is corrupt, and don't you dare try to change it, or you'll end up like Mort Friedman. Mort's story became a legend in Chicago. Everyone I talked to seemed to know about it, including, of course, Bob Cooley. I asked Bob whether he'd ever cross passed with Morden, if he knew him. I didn't know him personally, know when you heard what he was

up to, did you think it would succeed. No, I knew it wouldn't, he says. He knew it wouldn't, not just because the legal system protected itself, but because ultimately the mob was just too powerful, had too much of a stranglehold on the judicial system. They had control over everything. Right, this doesn't seem to register, and I don't. I'm not getting mad at you. I'm just saying you are like

most people. You think, well, it couldn't be that. Believe me, it was that powerful, and then some they were everything. This was one of those moments, by the way, where I could sense Bob's mounting frustration with me that I was so naive or perhaps thickheaded, that I just couldn't grasp the most fundamental law of his world. A system that is corrupt will stay corrupt, kind of like an object in motion will stay in motion until, of course,

someone stands in its way. And, as it turns out, over at the FBI, some of the gmen were getting ready to make a stand. They had taken notice of mort Friedman's failed crusade, and they were marshaling their agents, preparing an army of sorts. More on that when we come back after the break. Sometime after mort Friedman got rebuked. He says he got a call from the FBI. They had questions for him. They wanted to know how exactly bribes were being placed in Chicago's courthouses and who the

culprits were. Of course, mort would be the logical to ask. Even though his crusade had failed, he was still known as the guy who dared to take on corruption. Now. Little did Mort know, the FBI had hatched a major plan to expose corruption in Chicago's courts. They called it Operation Gray Lord, and ultimately the success of this operation would hinge on a young lawyer named Terry Hake. I didn't want to be a lawyer anymore. It seemed like a big game with what went on and what I

thought was going on in the corporals. This tape is from a TV interview he did years ago. Terry actually gave it to me. We chatted by phone a bunch of times, but he preferred not to be interviewed on the record. Terry was a prosecutor. He was young and sincere and principled. People who knew him well said he was like a boy scout, almost like two point zero, and he would try to succeed where mort had failed. He told the TV interviewer, my perception of the corruption

was that it was an old boys club. If you wanted to be one of the boys, you went along with the way things were done, and you paid money. Terry was so fed up that he was prepared to risk his entire career in order to do something about corruption. So the FBI convinced him to go undercover, posing as a corrupt lawyer. But the FBI was determined not to repeat the mistake that Mort Friedman had made, so instead of bribing officials in real cases, the FBI would stage

bogus crimes with bogus criminals, like a big charade. They started with DUIs Now. The way we would do this is we would drive like ten miles over the speed limit on the Dan Ryan Expressway. This is Bill McGarry. He was the FBI case agent in charge of Operation Gray Lord starting in nineteen eighty one. Bill would tell his undercover agent to get in the car and break the speed limit in the hopes that they get pulled over.

We would pour liquor on the shirt of the undercover agent so that the police officer immediately detected and smelled the odor of alcohol, and then the undercover agent would feign intoxication, you know, would slur his speech, stumble around, and sell and so forth. The thinking was the undercover agent would get arrested, spend a night or two in jail, then hire Terry as their lawyer. Terry would then attempt to place a bribe and document the whole thing. Pretty innovative, right,

But there was one serious problem. So what would happen is the police officers something would just not arrest the people. They'll remembers one time the cop took the car keys of an undercover agent and just threw them down the sewer. Another time, the cops pulled over one of his guys who was posing as a drunk driver, and they buscated his keys and locked them in his car, but they did not arrest him. Bill says his agents had a really hard time getting arrested, in part because the cops

knew how corrupt the system was. They knew that most of the time the people they arrested could just buy their way out of it. So what was the point. Bill did finally manage to get one of his undercover agents arrested for a dui but when they showed up in court to try the case, the presiding judge had too much to drink at lunch and court was adjourned. And this is how it went for months and months. Eventually the FBI decided to try staging more serious crimes,

including felonies. So we'd have an agent who would be walking down the street carrying back In those days, you had men who would wear these purses. Then another undercover agent, playing the role of the thief would steal the aforementioned and purse. There'd be other undercover agents playing the role of witnesses who just happened to be standing around when the crime was committed. One of these witnesses would wrestle the thief to the ground, the cops would get called.

Then it'd be here's the thief, we have them for you, and the whole scheme it actually worked. That's when Terry Haig entered the scene, playing the role of the dirty defense lawyer. Terry would go into the courtroom wearing a wire. Then he'd placed a bribe to get his client off. Here's a recording Terry made in which he paid off the bagman for a judge named John Divine Well here's a one fifty for roll behind okay, and verse fifty for you, oh you ceb in it? That okay? Good?

And then they had it, a dead bang crime on tape, a cleanly executed sting operation. And the FBI just kept staging these bogus crimes. There was even an office where agents sat around cooking up storylines and fake crimes, like a bunch of TV guys in a writer's room out in Hollywood. They came up with fake bios and phony IDs for everyone involved. They thought of every detail. They even rented apartments to back up the fake IDs, so if anyone got suspicious and started poking around, they'd find

an actual door to knock on. And the scale of this was enormous. Bill, the case agent, says that when all was said and done, he used over three hundred undercover agents, and the evidence poured in. Scores of bribes were documented, thousands of hours of conversations were taped, incriminating cops, judges, lawyers, and bag men, and it seemed like maybe finally the

city of Chicago was going to get cleaned up. And then one night in August of nineteen eighty three, three years after Great Lord began, word got out and the operation was secret no more. Bob Cooley remembers this August night when news of Operation Gray Lord broke because, as it turns out, he was throwing a bachelor party for his younger brother, Dennis. Bob says he invited two hundred people, mainly lawyers and judges, to his favorite haunt counselor's row.

Terry Hake, the lawyer who went undercover for Operation Gray Lord, he was there too, still very much undercover. Anyway, beer was flowing, glasses were clinking, and somewhere in the background a TV was on ron. The investigation has code named Gray Lord. It's the largest undercover investigation ever started by the United States Justice Department. Undercover FBI agents have methodically and systematically penetrated the criminal justice system in Cook County.

And then suddenly the partygoers were clamor around the TV to hear what was being said. They announced on the TV that somebody was working undercover and had been for a couple of years, and there was going to be major indictments coming down on the court system there in Chicago, and all the people that are going to be indicted are standing right there alongside of US. At this point, it was unclear who exactly was going to be indicted, nor was it clear who this undercover agent was, but

this much was certain. The ship was about to hit the fan. Bob says. The rollicking bachelor party got serious quick when they announced that on TV. Holy Christ, and we're all standing there. Who's standing right next to me but Terry Hack. Bob was literally standing next to the guy at the center of this whole thing. Of course, at the time, Bob didn't know that Terry Hack was the mole, the very undercover agent being mentioned on TV. Bob just thought Terry was another defense attorney. A few

months later, the full story came out. The FBI uncovered a system of bagman. These are the people who insulate the judges from the dirty money. Most of the time, the bagman are lawyers, cops, and court bailiffs. Terry Hack was out at as the mole, and then the indictments began to roll. Some of the investigators have called the Cook County judicial system the most corrupt system they've ever seen.

In total, ninety two officials were indicted, including seventeen judges, forty eight lawyers, ten deputy sheriffs, eight policemen, eight court officials, and a partridge in a pear tree. Yep, it was like Christmas Day at the FBI. So you might think, in light of all of this that Bob was biting his nails like he just dodged a bullet or something, or maybe his bullet was still coming. Nope, I was ultra careful when I did things, and I realized nobody

would dare you to cooperate against us. Terry Hag never fowned any information about me from anybody, because nobody would dare say something about me for fear of the something would happen to him. Bob says that Operation Gray Lord, as grand as it was in scope, did not indict a single first word operative, as he called them. The key guys at the Mob relied upon Gray Lord, bagged a whole lot of public officials, but it did not break the outfits choke hold on the city. I talked

to Bill McGarry about this. The FBI agent in charge of Operation Gray Lord asked him, did you suspect that the Mob was funneling its money into corruption? So we always suspected it, but we never, I think, had any hard evidence to suggest that you know that there was a lot of mom involvement in the corruption. So as incredibly impressive as gray Lord was in this regard, it fell short. Gray Lord indicted a whole number of people.

All that happened was only a few of us could still, you know, fix major cases, and the price just went up. You heard him right. Perversely, the outcome for Bob from Operation Gray Lord was that he could now charge more money for fixing a case because many of his competitors had either been locked up or frightened away. So to recap, first, Morte Friedman, the Babe in the Woods, tried to clean

things up and got crushed. Then the FBI, with its army of over three hundred undercover agents, waged its war. And still the mob seemed to have sway over the courts. They owned, politicians, they killed with impunity, They controlled the city. It seemed like they were untouchable. So what would it take to really end corruption in Chicago? Who would put an end to Bob Cooley and the corrupt system that he was part of, the answer, of course, was only himself.

Next time, undeep cover what's going through your head at that moment? Keep the fight going, don't back down and don't give up, and I kept telling myself don't shoot. Deep Cover is produced by Jacob Smith and Amy Gaines and edited by Karen Shakerjey. Our senior editor is Jan Guera. Original music and our theme was composed by Luise Gara and Fawn Williams is our engineer. Our art this season was drawn by Cheryl Cook, designed by Sean Carney. Mia

Lobell is our executive producer. Special thanks to Heather Fame, John Schnars, Carl Mcgliori Mayakine, Christina Sullivan, Eric Sandler, Mary Bett Smith, Brant Haynes, Maggie Taylor, Nicolemarano, Megan Larson, Royston Beserve, Lucy Sullivan, Edith Russlo, Riley Sullivan, Jason Gambrell, Martin Gonzalez, and Jacob Weisberg. I'm Jake Albert. Special thanks to investigative journalist Peter Carl who shared his insights on Chicago in

the nineteen eighties. If you'd like to know more about Operation Gray Lord, check out Terry Hake's memoir It's called Operation Gray Lord. He co wrote it with Wayne Klatt. Also check out Gray Lord by James Twey and Rob Warden. 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,