REDACTED: Declassified Mysteries with Luke Lamana
Operation Greylord: Chicago’s Corrupt Courts
Tue, 04 Mar 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.
Chapter 1: What is the story behind Operation Greylord and Chicago's corrupt courts?
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 Lowe 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 Lowe 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.
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Chapter 2: How did Bobby Lowe's testimony impact the case against Harry Alleman?
That night, after work, Haik drove back to his parents' house in the suburbs. Reedy had agreed that since Haik was still living there, he could tell them about going undercover. Haik 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, Haik gave Reedy his answer. He was in. Just a few weeks later, Haik 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. Haig 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 Olson, who was rumored to be the most corrupt man in all of Cook County and maybe even the whole country. Haik 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. Haik 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.
Haig 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, Costello took a swig of beer and told Haik 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. Haik 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.
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