REDACTED: Declassified Mysteries with Luke Lamana - Operation Greylord: Chicago’s Corrupt Courts

Episode Date: March 4, 2025

In 1979, prosecutor Terry Hake made a bold choice. He agreed to go undercover for the FBI and report on widespread corruption in the Chicago courts. As he navigated a world of bribery and backroom deals, Hake risked everything to take down some of the most powerful figures in Cook County’s justice system. But the deeper he went, the more dangerous his mission became.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterFollow Redacted: Declassified Mysteries with Luke Lamana on the Wondery App or wherever you get your podcasts. You can listen to new episodes early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting https://wondery.com/links/redacted/ now.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wondery Plus subscribers can listen to redacted, declassified mysteries early and ad free right now. Join Wondery Plus in the Wondery app or on Apple podcasts. This episode contains depictions of violence and sexual assault and is not suitable for everyone. Please be advised. In May 1977, a young man named Bobby Lowe took the witness stand in a packed Chicago courtroom. Lowe swallowed the lump in his throat and tried to focus on the prosecutor. The man he was here to testify against sat at the defendant's table, staring at him. He was one of Chicago's most feared mobsters, Harry the Hook Alleman.

Lowe took a deep breath to steady his nerves. Then he told the court what he'd seen one night five years ago. Lowe was out walking his German Shepherd and spotted his neighbor heading to his car. The neighbor was a Teamsters Union steward. Out of nowhere, a vehicle pulled up, and gunshots poured out of its open window.

The Union man was hit repeatedly and knocked into some nearby bushes. Before Lowe could process what he'd seen, he heard a car door open. Someone got out and headed straight toward him while pointing a gun. Lowe's dog lunged forward to attack. As Lo tried to hold her back, he locked eyes with the gunman. He was frozen for a second and then ran to escape.

The murderer's face was instantly seared into his memory. As Lo recounted his experience, he thought about everything he'd been through over the last few months. He'd been forced to quit his job, he'd been put in witness protection along with his wife and their four children, and moved between safe houses under a 24-hour guard. It was pure hell, but everything was building to this moment, the chance to put a murderer behind bars. The prosecutor asked Lowe if the man he'd seen that night was in the courtroom

today. Lowe nodded and pointed at the man who'd haunted his nightmares for so long. Harry Alleman. The mobster sat coolly in his flashy suit and silk tie, his eyes hidden under tinted glasses. The smirk never left his face. Lowe finished his testimony and was escorted out of the courthouse flanked by police. Now, all he could do was wait. Lowe wasn't the only eyewitness to the murder. Another neighbor had identified the gunman too, and the man who drove the car had also turned state's witness.

He gave a detailed account of the mobster's role in the murder. A few days after testifying, Lowe and his wife were in a car with federal agents. They were listening to the news on the radio, and the judge was about to read the final verdict. Lowe asked the agents to turn up the volume. When the announcement was read, Lowe was shocked. Not guilty. The judge said the state had not proved its case beyond a reasonable doubt, and not only did he acquit the mobster, the judge accused Lowe of lying on the stand. Lowe punched the seat in front of him, stinging his knuckles. He put his life on the line to testify against a violent mobster, and in the end, it had all been for nothing. To the mobster, the verdict was no surprise.

He knew the judge had been bought off. It had taken just $10,000 to throw a murder case. I would define reclaiming as to take back what was yours. Something you possess is lost or stolen, and ultimately you triumph in finding it again. Listen to Reclaiming with Monica Lewinsky wherever you get your podcasts. Scam Factory, the explosive new true crime podcast from Wondery, exposes a multi-billion dollar criminal empire. Every suspicious text you ignore, masks a huge network of compounds where thousands

are held captive and forced to scam others under the threat of death. Follow Scam Factory on the Wondery app or wherever you get your podcasts. From Ballant Studios in Wondery, I'm Luke Lamanna, and this is Redacted – Declassified Mysteries, where each week we shine a light on the shadowy corners of espionage, covert operations and misinformation to reveal the dark secrets our governments try to hide. This week's episode is called Operation Greylord – Chicago's Corrupt Courts. If you spend enough time in the military, you'll realize that just because someone has been in for a long time, or even if he has a lot of rank, that doesn't mean he's

a good person. One of the most frustrating aspects of military service is when you find out you have a corrupt or otherwise incompetent leader, and yet you still have to call him Sir. I'm not going to name any names, but one of the ships I was deployed on had several high-ranking Navy personnel, such as the ship's commander, that were caught taking bribes from sleazy foreign contractors. They scammed the U.S. Navy out of millions. All of them were arrested.

But even all of that doesn't hold a candle to how bad the Chicago judicial system was in the 1970s and 80s. During that time, Chicago's courts were a breeding ground for corruption. The system was rife with mob ties and bribery that let killers like Harry the Hook Alleman walk free. Brave witnesses like Bobby Lowe spoke out in cases with predetermined outcomes. Victims of horrific crimes, including rape, murder, and child molestation, were routinely denied justice.

Chicago's courts preferred to keep their dirty secrets hidden, but federal authorities had a plan to blow the lid off the whole corrupt system. They launched Operation Greylord, a covert investigation to expose and dismantle crooked local institutions. It would ultimately lead to the biggest corruption bust in U.S. history. At its center was Terry Haake, a young, idealistic attorney. Without him, Operation Greylord would never have been possible. In the fall of 1979, Terry Haake sat at the prosecutor's table in a downtown Chicago

courtroom. He was an assistant prosecutor just three years out of law school and he was about to question the victim and key witness in a rape trial. Haake watched as the teenage girl took the stand. Her voice was shaky as she began to recount her horrific ordeal. The teenager had been raped by her boss at the grocery store where they both worked. Her boss had chased her around the store, bitten her neck, brandished a gun, and threatened to kill her if she went to the police. The courtroom fell silent, absorbing the weight and horror of her

testimony. Haake sat down and waited for the defense attorney to rise for his cross-examination. Haake sat down and waited for the defense attorney to rise for his cross-examination. But the attorney chose not to question the victim at all. That was highly unusual. But a little while later, it all made sense to Haake. The judge dismissed the charges without any hesitation, letting the alleged rapist go free. After the trial, Haake pulled the girls' parents aside to talk. They were devastated, and he felt awful for making their daughter publicly relive her

experience for nothing. He did his best to console the girls' parents. He told the couple that the judge must have killed the case because there were no witnesses. He didn't have the nerve to tell the girl's family what he strongly suspected. He believed the defense lawyer had paid off the judge. As the girl's parents turned to leave, Haik heard footsteps approaching him. He turned to see the courtroom sheriff's deputy walking toward him. Her face contorted with anger. She demanded to know how he could have lost the case.

She told him to think about what his failure did to that poor girl and her family. Her words rang in Haake's ears as he drove home to his parents' house where he still lived. Haake had become a lawyer because he wanted to put bad guys behind bars. Now he felt disgusted with the profession and utterly helpless. He was starting to reach his breaking point. It had been two years since a judge found Harry the Hook Alleman not guilty of murder. At the time, Haake was shocked, but he didn't immediately conclude the system was corrupt. He later noticed it was part of an alarming pattern. Some judges seemed to be playing by an entirely different rule book when it came to the law. Some judges seemed to be playing by an entirely different rule book when it came to the law. The latest rape case proved it once again, and for Haake, it was the last straw.

Many judges were just as bad as the criminals in their courtrooms, some were even worse. Someone had to do something about this rampant corruption. Haake decided it might as well be him. Shortly following the court system's most recent failure in the rape case, Haake decided it might as well be him. Shortly following the court system's most recent failure in the rape case, Haake filed a complaint about the judge with the state's attorney and the special prosecutions unit. But his fight for justice would have some unexpected turns. A few months later, Terry Haake walked into his Chicago FBI office. He'd gotten a call to go there in the middle of the workday.

Haake wasn't sure what to expect, but he figured it had to be connected to his complaint. He made his way past the entrance, where photographs of former special agents hung on the wall. A receptionist ushered him into a room with a long oval table, where three Justice Department officials were waiting. The man in charge was an assistant U.S. attorney with dark brown hair and a reddish mustache. His name was Dan Reedy. Reedy asked Haake point blank if he'd ever taken a bribe. Haake shook his head and said no.

Reedy leaned over and pressed Haake. He demanded to know what Haake would do if he was offered money to throw a case. Haake said he would report it to his division. Reedy kept pushing. He asked if Haake knew anyone who took bribes. Haake said no, but he didn't need a personal connection to know what was going on. He said it was no secret that people were taking bribes, but he didn't know who exactly. He and other attorneys often speculated. After a long pause, Reedys stared straight at Haake and finally told him why the FBI had called

him in. They wanted him to pose as a corrupt prosecutor and take bribes to drop cases, and they wanted him to wear a wire so that they could listen in. Haake's heart was racing. He'd never expected a request like this. Reedy told him the government had long suspected something was rotten in the Cook County Courts. He said he had an entire folder filled with the names of judges, lawyers, and police officers who may be linked to corruption at the highest levels

of the system. But to root out the bad actors, they needed someone honest on the inside. Haake had been the only lawyer to make an official complaint about the corruption. Haake shifted nervously in his chair. He worried about what would happen to him if he took the job. He remembered the advice he had gotten one day outside the special prosecution's office. Don't ever rat on your colleagues. Besides, any corrupt lawyers surely had mob ties.

What if the mafia found out and showed up at his house? Haake also knew he wouldn't be the only one in danger. He still lived with his parents, and he had recently started dating someone that he was getting serious about. They could be in danger, too. Reedy promised Haake that the FBI would protect him, and they would keep the investigation tightly under wraps until it was time for him to testify. They were calling it Operation Greylord after a racehorse one of the FBI agents had gambled on and won. But Reedy did have a warning. If Haake agreed to go undercover, it would probably be the end of his career as a lawyer

in Cook County. The corruption went so deep that no matter who they put away, there would still be people who would see him as a rat. Haake understood the risks of taking on this assignment, but at the same time, a jolt of adrenaline ran through him. He'd always dreamed of working for the FBI. He'd even applied for a position there while he was in law school. His mind was made up.

He wanted to make a difference. But there was one person he needed to talk to first. That night after work, Haake drove back to his parents' house in the suburbs. Reedy had agreed that since Hake was still living there, he could tell them about going undercover. Hake didn't want to reveal anything to his father since he could never keep a secret, but he knew his mother could, so he told her what he was going to do. Her face fell.

She was scared. Haik tried to reassure her. He'd said he had dreamed of this moment ever since he was a kid, watching shows about the FBI on TV. Haik could see his mother understood, and reluctantly, she gave him her blessing. At his next meeting with the FBI, Haake gave Reedy his answer. He was in. Just a few weeks later, Haake was seated in a booth at a restaurant near the courthouse

frequented by lawyers. He was having lunch with a man he'd never thought he'd be sitting in front of, Jim Costello. Costello had a reputation as a crooked defense lawyer. He'd earned the nickname Big Bird due to his height and unruly hair. Haake thought of him as a hallway hustler, always ready to prey on defendants from low-income backgrounds. Costello would promise he could make their cases go away and told them he had the judge's ear.

The judge was Wayne Olsen, who was rumored to be the most corrupt man in all of Cook County, and maybe even the whole country. Haake really wanted to bring Olson down, but to get to him, he needed to go through Costello. The two lawyers had gone to the same university, but they made an odd pair. Costello was from the south side, a rough part of town, and he'd worked as a cop for years before becoming an attorney. That's where he'd learned how the justice system really worked. Haake was soft-spoken and had grown up comfortably middle class.

Many of his colleagues joked that he looked like a choir boy with his rosy cheeks. The FBI had even suggested he grow a beard to look older and tougher. Haake had taken their advice and sprouted a scraggly mustache, but he had just shaved it off. He figured he'd be a more confident mole if he felt comfortable in his own skin. As they waited for their food to arrive, Costello nodded towards some of the other prosecutors sitting in the restaurant. He called them dorks and said, they're making what, 25, 30 thousand a year and they think they're tough shit? Costello took a swig of beer and told Haake he knew how to get things done, and it wasn't by following the rules. He said there were certain ways to make things easier

for everybody. Haake was surprised at how openly Costello was talking about corruption. Even without Haik admitting to any illegal activity of his own, Costello had alluded to his connections with fixers who collected bribes. He seemed to be inviting Haik into his shady world. It worked. Later that summer, Costello stopped by Haik's office and handed him two $50 bills. He said it was for all the favors Haik had done for him. Haik hadn't done him any favors.

So it was clear Costello was trying to buy his help in the future. Haik reminded himself this was the whole point of the operation. He put the bills in his pocket. He was officially a crooked prosecutor for Chicago. Imagine this. You help your little brother land a great job abroad. But when he arrives, the job doesn't exist. Instead, he's trapped in a heavily guarded compound, forced to sit at a computer and scam innocent victims, all while armed guards stand by with shoot to kill orders.

Scam Factory, the explosive new true crime podcast from Wondery, exposes a multi-billion dollar criminal empire operating in plain sight. Told through one family's harrowing account of sleepless nights, desperate phone calls, and dangerous rescue attempts, Scam Factory reveals a brutal truth. The only way out is to scam their way out. Follow Scam Factory on the Wondery app

or wherever you get your podcasts. You can binge all episodes of Scam Factory early and ad free right now by joining Wondery Plus. At 24, I lost my narrative, or rather it was stolen from me. And the Monica Lewinsky that my friends and family knew was usurped by false narratives, callous jokes, and politics. I would define reclaiming as to take back what was yours. Something you possess is lost or stolen,

and ultimately you triumph in finding it again. So I think listeners can expect me to be chatting with folks, both recognizable and unrecognizable names, about the way that people have navigated roads to triumph. My hope is that people will finish an episode of Reclaiming and feel like they filled their tank up. They connected with the people that I'm talking to and leave with maybe some nuggets

that help them feel a little more hopeful. Follow Reclaiming with Monica Lewinsky on the Wondery app or wherever you get your podcasts. You can listen to Reclaiming early and ad-free right now by joining Wondery Plus in the Wondery app or on your podcasts. You can listen to Reclaiming early and ad-free right now by joining Wondery Plus in the Wondery app or on Apple podcasts. A few days later, Haik used surgical tape to strap a recording device underneath his left arm. He wore a t-shirt under his dress shirt, hoping it would hide the awkward bulge.

By the time he got to the courthouse, he was sweating and hoped it wouldn't drench the recorder. Hake tried to act casual as he approached Costello in the hall. He asked him to have lunch again, this time in the courthouse cafeteria. They loaded their trays with cheeseburgers and fries. After they sat down, Haik thanked Costello for the $100 he had given him. He said he had used it to take his girlfriend Cathy out over the weekend. Then he fished for information.

He was shocked to hear Costello admit he paid off Judge Olson nearly every day. Haik prayed his tape recorder was working. He tried to memorize everything Costello was saying in case it wasn't. The next day, Haik handed the tape over to his FBI contact, who told him he'd threaded the tape incorrectly in the recorder. But somehow, Costello's incriminating words had come through, loud and clear. In another conversation, Costello gave Haik a full rundown of how the system of fixers and payoffs worked. It was as if he were training a new employee.

Costello explained he had a deal with Judge Olson. The judge would send him defendants and Costello would give him 50% of his legal fees in return. Every Friday he dropped $500 or thousand dollars into Olsen's drawer. This was crucial information Haik could use to bring down the corrupt system. But he also wondered what some of his honest lawyer friends might think, watching him sit with Costello at lunch, day after day. While the system was full of corruption, there were still upstanding attorneys committed to doing their jobs. While the system was full of corruption, there were still upstanding attorneys committed to doing their jobs.

His girlfriend Cathy was on her way to becoming one of them. She was in law school, and her father had been a judge with an honorable record. And though Haake had been sworn to secrecy, he told her about his undercover work. Luckily, Cathy was proud of what he was doing, and promised not to tell anyone. All the other lawyers were left to guess what was going on. By hanging out with Jim Costello, Haake was making it known that he was open to taking bribes. As dirty as it felt, he knew this relationship would open up doors, even if he lost friends in the process. In October 1980, about five months after starting his undercover assignment, Haik walked up

to a swanky apartment building on Chicago's near north side. He was there to meet an old friend named Mark Ciavelli, who'd once worked alongside him as a prosecutor. That night, boxer Sugar Ray Leonard was facing off against Roberto Duran. Haake wasn't much of a boxing fan, but this was a big fight, so when Ciavelli suggested that they watched the broadcast in a local movie theater, Haake had agreed to go, and Ciavelli picked him up in his BMW. Ciavelli had left the state's attorney's office to become a defense lawyer, and it was clear from his luxury car, fancy apartment and tailored suits that business was booming.

The month before he'd approached Haik, suggesting he also ditch his career as a prosecutor and join his private practice. Ciavelli even admitted to bribing judges, telling him that was just how things worked. Haake had been shocked to learn that even his old friend was corrupt. It seemed like it was just a matter of time before he found out everyone he knew was taking bribes. But that evening Haake figured he and Ciavelli weren't going to talk business, just unwind. He could use a night off. The stress of working undercover was getting to him. He'd spent the last few months enduring boozy lunches and late-night binges with Big Bird

Costello and Judge Olsen himself, pumping them for information. Haake leaned back into the BMW's smooth leather seat. But as soon as they got on the road, Giavelli dropped some disturbing news. He and a guy named Bob Silverman, another one of the most corrupt attorneys in Cook County, had fixed a narcotics case in a suburban courthouse. Haake tried to hide his disappointment. He forced a smile as Ciavelli described the way he and Silverman had just bribed several judges.

Silverman had deep ties with the mob and was so confident about his fixes that he'd stroll into court for trial without carrying a single file or briefcase. He was known as Silvery Bob. He was a big fish and Haake wanted to reel him in. Ciavelli then described another business opportunity. There was a case coming to Haake's narcotics courtroom, which Judge Olsen would hear. Ciavelli asked him to drop the charges in exchange for a bribe. Haake played along, knowing he could use the offer to his advantage. He nodded and told Ciavelli he dropped the charges,

but it wouldn't be necessary to pay. He'd do it as a favor. Now he could go after not just the judge, but Silvery Bob too. The day before Thanksgiving, 1980, Haake was lurking anxiously in the hallway of the Cook County Courthouse. Most of the courts had closed early and everyone was trying to wrap up their work before the holiday. But that afternoon, Haik wasn't thinking about turkey and stuffing just yet. He was trying to look inconspicuous

as he kept his eyes glued on the door of Judge Olson's chambers. Two FBI agents disguised as repairmen were waiting nearby to bug the office. They had walked confidently into the building and unlocked the door to the switchboard room where operators managed the court's phone calls. Once Haik confirmed the chambers were empty, they would head in, pretending they were there for a repair. Olsen was on vacation, but he had a fill-in judge that must have been taking his job seriously. It felt like he would never leave. Finally, Haik heard the door open and then footsteps striking the marble floor. He walked quickly to a phone nearby and confirmed the office was empty.

A few weeks earlier, Haake had flown to Washington, D.C. to meet the director of the FBI and lay out all the evidence he'd gathered. By that point, Olsen had admitted to Haake that he had accepted thousands of dollars in bribes and with that admission the FBI had given him the green light to install the bug. It was the first time an American judge's chambers would ever be put under this kind of surveillance. The timing was perfect.

When Olsen came back to the office on Monday, lawyers would be clamoring to fix cases that they hadn't been able to under the fill-in judges. And now they'd be caught doing it on tape. While the FBI agents went into Olson's office to install the bug, Haake left and drove to a nearby supermarket. He met a female agent who accompanied him back to the courthouse in an unmarked car, ready to pose as his girlfriend. If the two FBI agents inside Olson's office ran into trouble, Haake and his fake girlfriend would run back into the building, claiming he'd forgotten his briefcase.

The ruse would hopefully cause enough of a distraction so the agents could slip away. As they waited for updates on Awake Talkie, Haake's mind raced through the worst-case scenario. What if someone came back unexpectedly, a janitor, or worse, one of Olsen's fixers? If anyone showed up in the chambers, it could blow the entire operation. But as luck would have it, the agents placed the bug without a hitch. By early December 1980, the FBI had been listening in on Judge Olson's chambers for more than a week. So far, the bug had recorded enough evidence to prosecute Jim Costello, the fixer attorney. But they still hadn't gotten Judge Olson clearly admitting he was in on the scam.

The judge had told Haake about plenty of his illegal dealings over drinks at their usual bar, but it had always been too noisy to bug. The FBI needed Olson to confirm on tape that he took bribes. That would be enough to charge him with federal crimes under the Racketeer-Influenced and Corrupt Organizations Act, otherwise known as RICO. Eventually, they got him, when the agents in the FBI listening room picked up a heated argument between Judge Olson and Costello. Olson wanted to know why there wasn't more cash in his drawer.

He'd written down he should have $2,300, but when Costello counted, he told the judge that there was only $800. The two men went back and forth about the number, and then, loud and clear, Olsen told Costello that yesterday they'd fixed eight or nine cases, so where was the rest of the money? The bug caught every moment of the fight. Haake was out in the hallway while it was happening, unaware of what was going on inside. He saw Costello storm out, looking like he was ready to punch someone. This disagreement over a few hundred dollars would not only reveal

their level of greed, it would cement the federal conspiracy case against Olson. Just a few days later, Haake got another big breakthrough. Bob Silverman, the mob-connected fixer his friend had been working with, passed him a bribe. Haake had been wearing a wire and caught Silverman discussing the payoff on tape. But Haake's elation was short-lived. He soon got some troubling news from his FBI contact. The bug in Olsen's office had picked up someone telling the judge that Haake had once applied for a job at the FBI. Haake felt his stomach drop. He understood immediately what it meant.

Maybe his cover had finally been blown. What's up guys, it's your girl Kiki and my podcast is back with a new season and let me tell you it's too good and I'm diving into the brains of entertainment's best and brightest. Okay, every episode I bring on a friend and have a real conversation. And I don't mean just friends, I mean the likes of Amy Poehler, Kel Mitchell, Vivica Fox, the list goes on. And now I have my own YouTube channel. So follow, watch, and listen to Baby,

This is Kiki Palmer on the Wondery app, or wherever you get your podcasts. Watch full episodes on YouTube, and you can listen to Baby, This is Kiki Palmer, early and at free, right now, by joining Wondery. And where are my headphones? Because it's time to get into it. Holla at your girl!

Hi, I'm Lindsey Graham, host of Wondery's Business Movers. In our latest series, media mogul Ted Turner Holla at your podcasts. Two weeks later, in the middle of January 1981, an assistant prosecutor pulled Haik aside in the back of the Narcotics Court. He spoke quietly, telling Haik there was something he needed to know. Haake braced himself for the bad news that Olsen had figured out his connection to the FBI. But instead, the prosecutor had a very different kind of warning. He told Haake that court insiders were calling him Terry Take behind his back.

He told Haake to watch out the next time he takes a bribe. Haake cursed the prosecutor out and denied that he was doing anything illegal. But on the inside, he was actually pleased. His cover as a corrupt fixer seemed to be safe. It also reminded him that there were still some honest lawyers in the Chicago courts. Shortly after that, on January 20, 1981, the FBI removed the bug from Judge Olson's chambers. By that point, they had captured more than 2,000 conversations between the judge and his many crooked partners. And if Judge Olson was on to Haake's FBI aspirations, he never let on.

For Haake, the mission was a massive success. That night he went out for a celebratory meal. He stopped at a busy restaurant in Little Italy, asked for a table for one, and ordered an Italian beef sandwich. But as he took the first bite, he looked across the room at couples, families, and friends eating together and realized just how isolated he had become. Working undercover meant living a double life. He felt lucky he didn't have to lie to his girlfriend Kathy. But instead of spending time with her, he was knocking back beers with low

lives like Jim Costello. And he didn't even like beer, because he was allergic to it. But Haik knew the work wasn't over. The worst was yet to come. Even with all the bribes and taped conversations, the FBI and Operation Greylord still needed more evidence to stop the corruption. They would start staging cases themselves, and they would need Haik to go undercover in a new role, this time as a crooked defense lawyer.

A few weeks after the bug in Judge Olson's office was removed, Haik was sitting at a restaurant near the courthouse, surrounded by Jim Costello and a few other corrupt fixers. Costello ordered another round of beers, and the waitress arrived with plates of fried food to soak up the booze. As usual, Costello's drunken voice seemed to fill up the whole dining room. He told Haake they would miss him and raised his glass for a toast. Haake had told everyone at the courthouse he was leaving the prosecutor's office and going into private practice as a defense lawyer.

So Costello had surprised him with this going-away party. For Haake, it was another reminder of how successfully he'd played the part of a corrupt prosecutor. These guys actually liked him and trusted him. At the end of the night, Costello pressed a wad of cash into Haake's hand as a going-away present. He told him to buy himself a new car. Up until now, Haake had been accepting bribes.

Now in his new role, he would be handing them out. It would be the next phase of Operation Greylord. While the FBI had been gathering evidence of bribes, their investigation was also allowing criminals to walk free in cases that they knew were fixed. But they couldn't do anything to stop them. The FBI now wanted to create their own crimes. They would manufacture cases from scratch and control every aspect from the criminal activity to the courtroom bribes. Agents flew into Chicago from around the country to pose as perpetrators and victims. It was awkward at first. The agents had been hired due to their respect for the law and their unwillingness to break

it, and here they were being asked to steal cars and guns and carry drugs. But Haake embraced the assignment. After months of anxiety, he found himself re-energized by his high-stakes role. In one made-up case, an undercover FBI agent was supposed to get arrested for drunk driving. As he careened through downtown Chicago, an FBI colleague called the cops to report him, but no squad car showed up. So the agent went so far as to drive the wrong way down one-way streets until the police finally pulled him over. In another staged incident, Haake played the role of a defense lawyer for a shoplifting suspect.

He approached the judge, telling him the evidence against his client was weak. The judge nodded in agreement, suggesting that Haake's client might have simply forgotten to pay for the items he had purchased. The judge later dismissed the case, but he didn't mention any kind of bribe payment from Haake. So Haake followed the judge to his chambers and asked if there was anything he could do to show his appreciation. The judge's response was cryptic,

Take $100, buy stamps and postcards, and write to all your friends supporting my re-election campaign. Haake was baffled, but then his fixer friend Costello decoded the message for him. He's telling you the first one's free, but the next one will cost you a hundred. A few years later, on August 5, 1983, Haake got a call from one of his handlers at the FBI. The voice on the other end of the line was low and urgent. He asked Hake if he'd seen the 5 o'clock news.

Hake had not. An investigative reporter had just gone on TV to break the story of a massive undercover operation aimed at rooting out corruption in the Chicago courts. Tonight, exclusive details of a huge federal investigation into the heart of organized crime in Chicago. Haake cursed under his breath. Who could have leaked the details of Operation Greylord to the press? But what the hell was this reporter doing?

Now that the investigation was public, anyone who was dirty would immediately clean up their act. In the days and weeks that followed, Haake was proven correct. One older judge, accused of accepting bribes, abruptly announced his retirement. Haake worried about what this meant for his personal life too. He and Kathy had recently gotten married and bought a house in the suburbs. Now he wondered if they would have to move to an entirely new state for protection. But while the existence of Operation Greylord was no longer a secret, the reporter had no idea that

Haake was the mole. As a result, Haake's own cover still hadn't been blown. So he told his handler that he wasn't ready to quit, and the FBI agreed to let him keep wearing a wire to record every dirty deal he could. His status as a mole wouldn't last much longer, though. Four months later, Haik was waiting for a flight to Washington, D.C. at O'Hare International Airport. He was carrying a briefcase full of incriminating tapes. And as he passed a newsstand, he spotted a headline about a former assistant state's attorney who had been working as a government mole.

He grabbed the paper and read the article. Haake's name wasn't in the story, but he knew it was all about him. And he knew Costello and all the other fixers would recognize it was him, too. Then, within days, someone did leak his name to the press. When Haake got back to Chicago, the FBI brought him and Kathy to a hotel to hide out. After three and a half long years, his time as an undercover agent had finally come to an end. In March 1984, Haake took the stand to testify in a federal corruption case for the first time. He looked out at the courtroom from behind the witness stand, trying to spot Cathy's face in the massive crowd.

He felt sweat seeping under his armpits. He wasn't used to being on this side of the courtroom. The trial was for a traffic court bagman named Harold Kahn. It seemed like a minor case, but it was pivotal for Operation Greylord. It would serve as a test of the approach the FBI used to gather evidence and whether they had followed proper legal procedures. An acquittal could potentially unravel all the FBI's cases against corrupt judges and fixers and other bagmen. Haik had spent the last several weeks reviewing tapes of Kahn and going over the case with prosecutors.

But he still didn't feel ready. The cross-examination from Kahn's defense attorney was tough. He accused Haake of violating the lawyer's code of ethics by lying, creating phony cases, and allowing his undercover FBI colleagues to testify falsely in court. Haake replied that he didn't think he was lying. He argued that a lie was something you said for personal benefit. Haake was acting on behalf of the people of Cook County, not himself. After the barrage of questions, Haake was finally able to step down from the stand,

exhausted. All he could do now was pray the jury would agree with him. A few days later, the jury found Kahn guilty of racketeering and extortion. He was sentenced to six years in prison. Haik breathed a sigh of relief. It seemed his more than three years of undercover work with Operation Greylord was actually paying off. Over the next decade, Haake testified 22 times as a witness, but no matter how often he appeared, he never shook off his courtroom nerves.

The defense attorneys called Haake a rat for stabbing his friends in the back. Friends like his old buddy Mark Ciavelli, the corrupt prosecutor turned defense lawyer. It also included the so-called friends he'd made undercover, like Jim Costello, the lawyer who taught him how to be a fixer. Ciavelli would ultimately strike a deal with the FBI. He would testify in exchange for avoiding criminal prosecution. One thing Ciavelli admitted eased any pangs of guilt Haake might have felt about betraying his friend. According to Ciavelli, Bob Silverman, the corrupt attorney with mob ties, had

threatened to kill Haake because he thought he worked for the FBI. Chiavelli hadn't even bothered to warn him. Not wanting to deal with the shame of standing trial, Silvery Bob would plead guilty for bribery, mail fraud, and racketeering. He was sentenced to seven and a half years in federal prison. Jim Costello was sentenced to six years. In all, more than 100 people were charged as a result of Operation Greylord, including 20 judges, 57 lawyers, nine police officers, and 17 court staff. These defendants are charged with a variety of federal crimes, including racketeering, extortion, mail fraud, and conspiracy.

All of them in connection with the alleged corrupt disposition of cases pending in the Circuit Court of Cook County. Three judges died before they were ever indicted, including two by suicide. Judge Olson received 12 years in prison. He died at the age of 63 while still behind bars. In 1986, Operation Greylord ended. A corrupt attorney named Robert Cooley came forward

to the FBI about his involvement in fixing cases and agreed to wear a wire. One of the first things he admitted was that he had paid a judge $10,000 to find Harry the hook Alamon not guilty of murder back in the late 1970s. In 1997 Bobby Lowe, the eyewitness who had seen the murder while walking his dog, returned to the stand to testify along with Cooley. That year, Alamon was finally convicted. Terry Haake's undercover work paved the way for a distinguished career with the FBI. He became a full agent within the Department of Justice. Despite the FBI's warning that

he would never work as a lawyer in Cook County again, he eventually did make it back to the Chicago courts. After retiring from the FBI, he went to work for the Cook County Sheriff's Office and eventually the state's attorney's office, the same place he had started his legal career. Operation Greylord exposed

how corrupt Chicago's judicial system had become, where justice was offered to the highest bidder. Terry Haake was a young lawyer thrust into this murky underworld. He discovered that sometimes the most dangerous conspiracies unfold not in far-off lands, but in local courtrooms and city halls, in the very institutions meant to serve and protect us. Follow Redacted, declassified mysteries on the Wondery app, Amazon Music, or wherever you get your podcasts. You can listen to every episode of Redacted early and ad free right now by joining Wondery

Plus in the Wondery app or on Apple podcasts. Before you go, tell us about yourself by completing a short survey at Wondery, this is Redacted, Declassified Mysteries, hosted by me, Luke Lamanna. A quick note about our stories. We do a lot of research, but some details and scenes are dramatized. We use many different sources for our show, but we especially recommend the book Operation Greylord, the true story of an untrained undercover agent and America's biggest corruption bust by Terrence Haake and news articles on

Operation Greylord from the Chicago Tribune. This episode was written by Susie Armitage sound designed by Andre Plouz. Our producers are Christopher B Dunn and John Reed. Our associate producer is Ines Rinique. Fact-checking by Sheila Patterson. For Ballen Studios, our head of production is Zach Levitt. Script editing by Scott Allen. Our coordinating producer is Samantha Collins.

Production support by Avery Siegel. Produced by me, Luke Lamanna. Executive producers are Mr. Ballen and Nick Witters. For Wondery, our senior producers are Loredana Pellavota, Dave Schilling and Rachel Engelman. Senior managing producer is Nick Ryan. Managing producer is Olivia Fonte. Executive producers are Aaron O'Flaherty and Marshall Louie. For Wondery.