When I first heard about this investigation a few years ago, I was immediately blown away: A cop going undercover to investigate his own colleagues? It was like some kind of cross between Serpico and Donnie Brasco. And when I learned the particulars of the case, it was every bit as daring and cinematic as I had anticipated. I knew I had to find a way to tell the story.

—David Howard

Illustrations by Guang Lim | Edited by Brendan Spiegel

Standing in the bathroom of the 15th District precinct, Silky pulled off his shirt and dropped his pants as the cop stood in front of him, watching closely. Silky was anxious, of course, and worried: Getting dragged into the police station — especially this police station — was plenty dangerous. At least he wasn’t wearing a wire, which was what the cops were looking for.

But mostly, it was just surreal. He’d heard of or seen dirty cops do just about everything: steal, lie, plant drugs on people, pummel them. But a strip search? That was new.

Silky focused on staying cool as he pulled down his underwear and bent over so that Cornelius “Peanut” Tripp, a member of the Chicago Police Department’s elite plainclothes tactical unit, could finish his inspection. He had nothing to hide — at least not where the cop was looking.

Officer Tripp ordered him to put his clothes back on. But Silky knew that the encounter was far from over.

Hanging out at the McDonald’s on Madison and Kildare earlier that evening — May 2, 1996 — he’d been expecting the cops to come for him. Word had gotten around that Silky was a new player in West Side Chicago’s crime-infested Austin neighborhood, having recently expanded his turf from the South Side. People on the street were talking about how he was a high-level cocaine supplier who traveled with lots of cash. Around here, that kind of reputation made a guy a target. He’d already been rolled by the cops in Austin several weeks earlier — they had taken $4,000 off him before uncuffing him and cutting him loose.

In particular, Silky had been expecting a visit from the cop working as Tripp’s partner that night — Edward Lee “Pacman” Jackson. Both Pacman and Tripp were part of a unit created to squeeze drugs out of the city’s neighborhoods, but they seemed more interested in squeezing cash out of the drug dealers. Pacman, in particular, was known as a guy who treated the streets like his personal ATM machine. Silky had heard that if Pacman, 26, pulled over someone who possessed something he wanted — money or information or just about anything else he deemed desirable — he was used to getting his way. If his target refused, he would dangle a packet of cocaine and threaten an arrest: Either I get that, or you get this. Shorten “packet” to pack, and that’s where the nickname came from. He was Pacman.

Pacman and Tripp had cuffed Silky at the McDonald’s, mashed him into their ratty unmarked car, and driven him to the 15th District — which in itself was a surprise, because Silky had figured they would simply take his money and move on. Inside the precinct, they’d linked Silky’s cuffs to a wall, then Pacman explained the situation: He would plant drugs and a gun on Silky, which would bring heavy felony charges. It didn’t matter that Silky only had a scale and empty wrappers in his car. He was on parole and carrying $10,000 in cash. Pacman pointed out that, in the course of fighting such extensive charges, Silky would inevitably spend 15 or 20 grand in attorney fees. Fortunately, there was an alternative: Silky could just hand over the $10,000 he was carrying and walk out the door.

For a while, Silky stood firm: “You’re not gonna take all my money, man,” he said. “I’m just not gonna let you do that.”

But eventually he agreed to give up the cash — and that’s when Pacman and Tripp decided they’d better cover themselves. After the strip search, Tripp brought Silky back into the interrogation room, where Pacman now moved in close and asked a pointed question: “Man, are you a fed?”

There wasn’t anything particular about Silky that suggested he might be associated with the Federal Bureau of Investigation (FBI). It was just that in that part of town, rumors of the feds sniffing around the activities of the Chicago Police Department (CPD) were as common and predictable as lake-effect snow in February.

Silky looked him in the eyes. “Fuck you and the feds, man,” he said. “I’ve been to the penitentiary — the feds put a case on me before. I hate the feds more than I hate you.”

They went back and forth on Silky’s history for a while, until Pacman let him walk. His pockets were noticeably lighter, but they even let him carry his scale out of the building.

It was true, Silky wasn’t in the FBI. But he wasn’t who he said he was either. His real identity was even more unfathomable — and the corrupt cops who had just shaken him down had no idea what was coming for them.

Lee Walters was only 33 when he arrived at his first big-city FBI post in February 1995. He’d spent his first five years as an agent in Little Rock, Arkansas, and he was stoked about his transfer to Chicago, even though he was initially assigned to a unit working on health care fraud, which he found tedious. “It took me six months to figure out how to get off of that,” he says.

His next assignment — the public corruption squad — promised to be far more interesting. His first day, his supervisor dropped a file on his desk. “Take a look at this pending inactive case,” he said. That was bureau-speak for Make this go away. A few other agents had walked around it and gotten nowhere. Agents had a term for such cases: a dog.

Opening the file, Walters read about reports of police corruption in the Austin neighborhood and quickly understood why: Investigating cops was difficult and dangerous. They were armed, of course, and they usually knew far more about what was happening than any out-of-town agent did. On top of that, the city’s most powerful people don’t necessarily want police corruption scandals complicating their time in office — or their legacies. If Walters truly tried to investigate, there was no way to know how much support he’d get, if any.

Walters’ boss returned with a slip of paper bearing the name of some contacts for Walters to reach out to, one of whom was Sgt. Gene Shepherd of the CPD’s Internal Affairs Division, or IAD (the unit has since been renamed the Bureau of Internal Affairs). When Walters reached out, Shepherd told him how, while hanging out in a West Side bar called Brothers Lounge, doing surveillance work for a different investigation, he had struck up a conversation with a woman. “While we’re sitting there talking, one of her friends came in, and the first thing she said — it blew my mind — she said, ‘Girl, let me tell you what happened to my cousin yesterday. That damn Pacman.’”

The woman introduced Shepherd to several other friends who all had similar stories: Pacman and his crew shaking people down, conducting warrantless raids and searches of houses, taking thousands in cash and drugs that they sometimes gave to informants — or other dealers — to sell, and in some cases selling the drugs themselves. One woman Pacman had arrested for dealing later said she figured she had no chance going up against a cop in court. “I know they was going to believe him because he was a police officer,” she told a reporter.

“Couple that with what I’d already known from the street,” Shepherd says, “and from other policemen talking about this guy, I said, ‘Man, this Pacman is really causing a lot of havoc.’”

Shepherd, then 49, had mostly been a loner during his 25 years on the force. Growing up as a Black kid on the South Side, he’d never really considered police work. After serving in the Army, he’d enrolled at the University of Illinois, and then in 1969 he attended a speech by the Rev. Jesse Jackson in which the civil rights leader encouraged more Black men to take tests to become police officers and firefighters. Shepherd’s friends encouraged him to apply — which he did just to help with Jackson’s campaign. “I was a business major,” he says. “I wasn’t thinking about the Chicago Police Department.” But in 1970, he was offered a job, and he decided to take it.

He was assigned to patrol in the Fifth District, on the South Side. Racism was rampant. One night while he was in the station, he smelled pepper spray and heard a struggle. He went back to the holding area and encountered two white cops beating on a Black man. “I politely asked them to stop, and they said something smart to me,” Shepherd recalls. “So, I had to pull out my gun, and I said, ‘You hit the guy again, I’ll shoot you.’”

When they stopped, Shepherd went to the watch commander’s office and reported the incident. “Things snowballed from there,” he says. When word got around, he found himself getting frozen out. “Being a person who spoke up back in — we’re talking 1971, ’72 — that was a different world back then,” he says. “I got a little flack for that.”

Rather than try to ingratiate himself, Shepherd made it a policy to simply be who he was and let everyone know where he stood. “I developed a reputation for a guy who would let people know right away: ‘Listen, I don’t take money. I’m not going to jail. ... So, if you want to do some dirty stuff, I’m not your guy.’ And that worked. I worked with some guys who the first thing they told me [was], ‘If you don't take money, I don’t want to work with you.’ I said, ‘Great. I’m gone.’”

When he joined the narcotics division in the 1980s, he went undercover, posing as a local drug user. He developed a relationship with a dealer that netted some of the first crack cocaine the department had seen. He also convinced the guy to show him how he made it. But he only lasted for four months in narcotics because most of the other cops in the squad didn’t want him coming along on their raids. Later he wound up in internal affairs.

A few days after Lee Walters reached out, he met Shepherd and another IAD officer named Joe Airhart at a downtown fleabag motel. Shepherd detailed what he’d learned about Pacman, who was rumored to be a member of a West Side gang called the Conservative Vice Lords. After spitballing ideas for a while, they came up with a plan: They would set up an undercover agent to pose as a drug dealer who carried around rolls of cash. Then they would make sure Pacman heard about him. As Shepherd put it: “We’ll present an opportunity for them to do what they normally do.”

Despite Shepherd’s experience with going undercover, putting him in a similar role in the Pacman investigation made little sense: By then he had 25 years on the force and had worked all over the city, including as a member of the Gang Crimes Unit. A cop with a quarter-century on the job would have a hard time going unrecognized by other cops. Walters sent out a request for an FBI agent from out of town.

They would have to find someone good. Pacman and his colleagues would be familiar with many of the investigative techniques the FBI might use. And if the allegations were true, Walters and Shepherd would be going up against some of the city’s most dangerous and well-armed criminals. But that’s what they were there to do.

They decided to call the investigation Operation Broken Star. (Chicago police officers wear stars rather than badges.) Shepherd’s boss, Assistant Deputy Superintendent Michael Hoke, the head of IAD, was on board from the start. “The area’s dope dealers were saying they would rather be caught by us ... than being caught by the Austin District Tactical Team and getting beat up and robbed,” he later told Law and Order magazine.

Hoke’s contacts in the CPD’s narcotics unit passed along an informant Shepherd and Walters could recruit for the operation. Myron “Bougie” Robinson was 6 feet tall and 275 pounds, and he had survived being shot four times in his grandmother’s front yard for stealing someone’s drugs. Bougie knew the landscape of the neighborhood and sometimes tipped off the cops about dealers or houses they could rob in exchange for a cut of the proceeds.

The nationwide search for an undercover agent had not yet panned out, so Walters recruited a Chicago-based FBI agent to help them get started. The idea was simple: Bougie would tell Pacman that he had an acquaintance who wanted to buy some cocaine; the cops could show up and take her money. The meetup would take place behind a West Side factory.

As Shepherd and Walters filmed from the building’s fourth floor, the cops pulled up in a “raggedy-ass Chevy Capri, which is a standard tac-unit car,” Walters says. Two men emerged. “It all kind of played just like it should have.”

Walters and Shepherd were too far away to see exactly what took place, but it looked like a standard shakedown at gunpoint. “From my vantage point, I didn’t see a gun, but the guy had his hand up like he had a gun,” Shepherd says.

But when Bougie and the agent came up afterward, there was a problem: She couldn’t identify anybody. She’d been nervous and was shaken, and she didn’t recognize the two cops from the photos she’d been shown. “It let all the air out of my balloon,” Shepherd says. “I said, ‘Oh my God, we don’t know who these people were.’”

Over the next few days, when Walters and Shepherd scrutinized the video, they realized that Bougie had set them up. Nervous about approaching Pacman, he’d instead invited a couple of friends who resembled the police. Walters and Shepherd were angry, but rather than cut him loose, they decided to keep him on and babysit him more aggressively. After that, Shepherd says, “We always had somebody with him. If he ever made a phone call, we were right there to listen to what he had to say. We had him on a very short leash.”

It wasn’t like they had a choice either. Everyone else was too afraid of the cops to help. Another would-be informant named Ronnie had spurned their offer of $2,000 to work with them. “He just threw it back at me,” Walters says. “He was like, ‘You’re gonna get me killed for 2,000 bucks?’”

As they dealt with that mess, Walters was still coming up empty in his search for an undercover agent. No one assigned to warmer locations was eager to spend a winter in Chicago interacting with corrupt cops, Walters says. It was a dangerous and largely thankless job. And the FBI offered no incentives for playing the supremely hazardous role of investigating corrupt cops.

With the case ready to stall out before it even started, Shepherd raised his hand, volunteering to go undercover while Walters continued looking, even though Shepherd was uneasy about the proposition. “Hey, listen, I’ll do this,” he told Hoke. “But I can’t be out there too long, because I know that somewhere along the line, somebody is going to recognize Gene Shepherd.”

Walters was far from convinced that this was a good idea. He had wanted someone from the Bureau who had no connection to Chicago. It was at best a “longshot,” he says — but Shepherd at least had been in the IAD for a number of years, rather than on the streets. And with a solid disguise, Walters figured it was worth a try.

Shepherd had one requirement: He didn’t want to be involved in an investigation that netted only minority cops. Throughout his career, he had observed that Chicago’s criminal justice system — like that of the entire nation’s — seeming to be weaponized against men of color. Pacman was Black, but there was evidence that he worked with other cops, in the tactical unit and beyond, and Shepherd wanted to make sure that the investigation wouldn’t be limited in any way.

With that, Shepherd began his transformation into Silky. The FBI provided him with a false background, address and Social Security number, as well as a criminal record that included numerous drug arrests and a 62-month sentence in a California federal prison. He would drive a burgundy Cadillac Seville and a convertible BMW and rent an apartment in Chicago’s Gold Coast neighborhood that was fully wired with video and audio recording devices.

Shepherd had a gray streak in his beard that had earned him the nickname Blue Beard on the South Side. He dyed that black, grew out the beard, and used makeup to cover a birthmark on his neck and chin. He topped off his makeover with a collection of kufis and colorful dashikis, high-end clothing, and a tasteful collection of rings and necklaces — stuff that looked expensive but was age-appropriate. Finally, Shepherd came up with the nickname, which came to him as he pictured the character he was about to morph into. “We’re trying to be smooth and easy,” he says.

It may have been a longshot, but it was the best they could do. And as reluctant as he was, Shepherd wasn’t surprised that Walters couldn’t find anyone else to play the part. “Trying to find a policeman to go undercover and work, especially against another policeman, is a daunting task,” he says. “You’re gonna lose some friends, naturally. And I guess I was the kind of guy for because I didn’t have a lot of police friends to begin with.”

When two cops in Austin pulled their guns on him, Silky was ready.

It was the night of March 13, 1996. Over the previous few months, Bougie had frequented Pacman’s barbershop, My Place, chattering about Silky. As word of Silky spread on the streets, Walters had obtained wiretaps for cellphones and landlines used by Pacman and several of his crew.

Earlier that day, Bougie had mentioned that Silky would be driving his Cadillac, flush with cash, to a West Side chicken restaurant. Soon, two cops — M.L. Moore and Lennon Shields — rolled up. Walters was filming from a surveillance vehicle disguised as a Chicago Transit Authority van. The officers jumped out and handcuffed Silky, then loaded him into their car.

Shepherd was surprised that neither of the cops was Pacman, whom he’d studied in photographs, but he rolled with it. “You can’t control who’s coming and what’s going to happen,” he says. “You just got to play the game when it’s presented to you.”

Staying in character, Silky explained to the cops that he was on parole and asked if there was anything he could do. Moore asked what he had in mind, and Shepherd offered $1,000. The cops drove around the neighborhood for a while, talking, before pulling into an alley.

“These guys, they played the game just like they were supposed to in terms of Pacman’s operation,” Shepherd says. “I knew when they got me in the car, we would talk. And I knew that they were ready to steal.”

The alley prevented Walters and the rest of the surveillance team from watching, which spiked everyone’s blood pressure. “We had no way to know what these cops were doing with Shep, and no way to know what they might do,” Walters says.

Shepherd had also refused to wear a wire, which meant no one could hear anything either. Walters had deferred to Shepherd’s experience — and the fact that Shepherd was the one putting himself at risk. “I was smart enough to be like, ‘OK, we’re gonna go with what he says,’” Walters remembers. But he found the experience excruciating: “You’re kind of sitting on the edge of your seat. You can plan for a lot of things, but you don’t control anything once it starts going.”

Moore told Shepherd that $1,000 wasn’t enough, and he reached down and pulled a wad of bills totaling $5,000 out of Shepherd’s front pocket.

Damn, man, don’t take all my money,” Shepherd told them.

The cops began talking about how much would be enough. Shepherd mentioned that he was carrying five grand because he knew the game. If you were a dealer and you said you had $3,000 when you really had $5,000, the cops would skim off two grand before they even started negotiating. “Most policemen who are thieves, they all got the same MO,” Shepherd says.

The cops offered to give him back $1,000. Shepherd objected, but Moore tucked that amount back into his pocket, then uncuffed him and pulled him out of the car.

With that, Silky was off and running. “Once I get them to bite that first time,” Shepherd says, “I’m straight.”

As spring blossomed in Chicago, the investigators worked toward the second encounter, which led to the strip search with Pacman. Just a few weeks in, the cops had already stolen $14,000 from Silky.

After the strip search, Shepherd felt sure of two things. One was that if there had been any remaining doubt about the rot in the 15th District, it was now erased. He was stunned that Pacman and everyone else on duty that day had let him walk out with the scale — an unmistakable tool of a dealer’s trade. “You gonna let me walk out of here past all them cops carrying that scale?” he’d asked Pacman, who had nodded.

“I didn’t believe it,” Shepherd recalls, “but I said, ‘I’m gonna try it.’ And nobody said a word.”

The other certainty: Whenever Silky was on the street in Austin from now on, he was a target.

In some ways, this was unnerving. The team had confirmed Pacman’s active participation in the Vice Lords gang. And despite months of searching, Walters had been unable to find a replacement for Shepherd, and they’d never shaken concerns that Shepherd would be recognized, or that they would trip up in some small, seemingly insignificant way that would sabotage their work. They knew they needed more evidence to arrest Pacman and his crew and take them to trial. And they knew there were a lot more corrupt cops out there that they wanted to get.

Shepherd also worried about his colleagues in internal affairs, the unit he’d been assigned to over the past eight years. The CPD tried to seal off the IAD from the department at large; it was located in an unmarked industrial building apart from police headquarters. Shepherd only reported to two superiors, per protocol, but beyond that it wasn’t clear where word of their activities traveled. “The one thing about the people at the IAD,” says Shepherd: “I didn’t trust half of them.”

For that reason, Shepherd and Walters met at a greasy spoon most mornings to discuss strategy, or they sat in a car and talked. When they had to be in the office, they limited their meetings to the smallest number of people possible.

As the investigation rolled into summer, Walters and Shepherd expanded their approach, employing new strategies to gather evidence of the depth of corruption in Austin.

Silky invited M.L. Moore and another cop, Alex Ramos, to a 15th District apartment to float an idea: Instead of being adversaries, they could be partners. Silky proposed that he hire the officers as chaperones when he was moving large quantities of cocaine around the city, or down to Indiana, or up to the North Shore suburbs: “I’d like to get one of you cops to maybe kind of like protect my guy,” Silky said in a meeting filmed by hidden FBI cameras. He offered $3,500 per shipment. Moore gave Silky his pager number.

Walters recruited Daron Council, a New Orleans-based FBI agent, to play the part of Silky’s mule. In late summer, Silky and Moore met at a McDonald’s on Mannheim Avenue, then headed to O’Hare. This was pre-September 11, when people were still allowed to walk up to an airport gate and greet passengers as they disembarked. Council strolled off his flight and Silky introduced him as a guy who helped him move large shipments of drugs.

Soon afterward, Silky met Moore and Council in a remote parking lot. Walters and Shepherd’s team had wrapped up some dummy kilos of cocaine. As Moore watched from Silky’s BMW — which was wired with microphones — Council moved the packages into his vehicle. Shepherd had instructed him in advance to drop one of the phony bricks in full view, so they could capture Moore’s reaction. “Oh my God, they dropped one,” Moore gasped. It was as if someone had dropped a baby, Shepherd thought.

Moore was “really on board now,” Shepherd says. “He’s talking, getting all excited” about playing a part in Silky’s operation. Moore then followed Council to a delivery at 176th Street and Torrance to ensure that the trip went smoothly. Moore understood that his job wasn’t to protect Silky’s crew from criminals, but from other cops. If someone in uniform pulled them over, he would intervene, flash a badge, make up a story about what was going on.

Everything went smoothly, but Shepherd felt that something about Council was off. They had both signed out some Rolex watches and jewelry from the FBI as part of their disguises. Shepherd returned his that evening, but Council kept his stuff. Shepherd figured maybe the FBI policy was different for agents, but he still felt something was wrong.

Silky was in a tight spot. He had once again been hauled into a police station, and this time he was standing in front of cops that he knew.

It was autumn now, and Shepherd and Walters had decided to expand the investigation — to see how far Pacman’s reach extended. Bougie had spread the word that Silky would be visiting a shopping mall in the 25th District. The surveillance team this time included another internal affairs officer. Beforehand, Shepherd had taken him around the mall parking lot where the encounter would likely go down. “Listen, when you get into a parking spot, you can’t move,” he’d said. He expected that if he was taken into custody, the cops who grabbed him would be vigilant about making sure they weren’t being followed.

Pacman apparently had other business that day, so he called a couple of friendlies in the area. The officers — both white — had grabbed Silky and stuffed him into to their vehicle. “When they got me into the car, I knew from their conversation they came to steal,” Shepherd says. “They’re cussing me out, calling me names, the N-word about 35 times.”

The older of the two officers was clever, Shepherd says. He called in a second unit and asked them to park up on a nearby knoll and watch the area — installing his own surveillance unit. Then he drove Silky to a different area of the parking lot. The IAD surveillance officer, ignoring Shepherd’s instruction to remain stationary, drove to a different spot to get a better view. “When he made that move, this cop was astute enough to say, ‘Hey, wait a minute, something’s not right — that car moved when I moved,’” Shepherd recalls.

The officer asked his colleague on the knoll to go check the mystery vehicle. When confronted, the IAD cop admitted to working for internal affairs. “That was mistake number two he made,” Shepherd says. This information was radioed back — and after the cops holding Silky heard the letters IAD, they abandoned the plan to take Silky’s money and instead drove him to the 25th District.

The officer, clearly spooked by the events in the parking lot, called for the asset forfeiture unit to come and run Shepherd’s money through a money counter — part of the process of seizing and recording evidence. “Now they’re trying to play it by the book,” Shepherd says.

When the asset forfeiture officer showed up, Shepherd recognized him as someone he’d worked with years earlier, in the department’s Area 1, on the South Side — and felt a wave of anxiety wash through him. He said to himself, “Oh my God, this guy might recognize me. I’m trying to do the best I can not to look like Gene Shepherd.”

The cop stared at him for a beat, then started asking questions: “Where are you from? I know you from someplace.”

Fighting to stay calm, Shepherd figured that he just needed to give the cop a plausible explanation for why he looked familiar. He knew the cop had worked Area 1, so Shepherd started naming gangbangers from those streets who would likely have been known to anyone who had worked there.

The cop nodded, but wasn’t convinced. He went upstairs to the detective division and asked whether anyone had worked in Area 1. Four guys piped up, and the cop called them downstairs.

Shepherd felt a fresh jag of nerves when he recognized at least two of the new faces. My jig is up, he thought.

“One of the guys questioned me about who I knew, where I came from. And I gave him a whole lot of crap, but he kind of said, ‘Yeah, he looks like someone, but that’s not the guy I was thinking about.’” And walked away.

Of the three remaining cops, one seemed to recognize Shepherd. “Yeah, I do know his face — it’s real familiar,” he said.

“Well, you know, I’ve been arrested numerous times, man, you can check my record out,” Shepherd said. “I got arrested four or five times at 51st Street.” Then he named a couple of notorious incidents that everyone was likely to remember, and said he’d been taken in for questioning.

“It made them think,” Shepherd says.

They all kept saying, “Yeah, I know that guy” — but ultimately, to Shepherd’s enormous relief, no one could identify him. They finally let him walk out with his money.

Pacman sounded agitated. He was tearing up a drug house, and he wasn’t finding everything he wanted. Or so he claimed, as Shepherd and Walters listened in on their wiretap.

Walters and Shepherd had heard that one of Pacman’s alleged tactics was essentially a home invasion: entering a building without a warrant, conducting a search, taking what he pleased. They decided to see if that was the way it would play out if they offered Pacman the opportunity.

In November, they set up an Austin apartment as a drug factory, with duct tape and cut-up wrappers and crushed aspirin scattered across a table. “It was as legit as you could make a place look,” Walters says. “We wanted to make it look like they just missed a big payday — the drugs and the cash.”

They hid $25,000 in cash in a false wall panel inside the closet and scattered some jewelry around the apartment. Then they loaded the place with hidden microphones and cameras, including one in a lamp. Once they were set, Bougie tipped off to Pacman with the address.

Pacman raided the place with two other cops. Once inside, he repeatedly called Bougie for instructions about where the money was hidden, as Shepherd and Walters listened in. FBI videotape shows the cops stuffing cash into their bulletproof vests.

In a final call to Bougie, Pacman claimed that they hadn’t found as much as they’d expected. “There wasn’t nothing but 13 (thousand) in there,” he shouted. “We went in, there wasn’t nothing in there.” Pacman, of course, had a motivation: The lower amount meant a smaller cut for Bougie.

Still, Bougie collected a reward of $2,000 and a gold chain left for him under a car at a beef stand in Oak Park. The other two cops netted $5,000 each.

The FBI’s phone surveillance of Pacman and his crew was valuable to more than just Operation Broken Star. Walters shared information with the FBI’s gang squad, as well as with the Chicago PD narcotics unit, which was working a case involving T-Fly, a dealer who was a Pacman associate.

One evening, a couple members of the narcotics unit stopped Pacman, who showed his badge, expecting the usual free pass — but instead, the narcs searched his car. Walters and Shepherd were listening as Pacman reacted afterward. “Man, there’s something going on,” Pacman said. “The police just stopped me, and they didn’t let me go — they searched my car. So we got to be careful.”

Walters, Shepherd and an IAD colleague, Joe, headed to the office at around 1 a.m. to discuss the situation. Shepherd felt that they should try again to expand the case beyond the core group and zero in on some of the white cops who had turned up in their net. He was uncomfortable that all seven of the cops they’d built evidence against were either Black or Hispanic men, and mostly young. It was a mirror image of the demographic disproportionately targeted by the American criminal justice system. The problem was, the fiasco with the two white cops in the 25th District had changed the vibe there. “From that point on,” Walters says, “they were everything by the book.”

Walters recalled another time when two white cops had stopped Shepherd and seemed on the verge of taking his money. Out of nowhere, in the middle of the interaction, they had received a call. Suddenly, they reversed course and started following normal protocols. “Their whole attitude changed,” Walters says. He was convinced that someone had alerted them to what was going on.

Still, Shepherd thought that there were at least a few white cops there who were linked to Pacman, and he felt that they could still be included in the operation — or at the least offered another chance to shake down Silky. As Walters and Shepherd debated how to proceed, Airhart disappeared. Shepherd believed that Airhart had been installed by his boss, Michael Hoke, to report back on the progress of the investigation. (Hoke could not be reached for comment for this article, and Airhart died in 2008.) This made for a tense dynamic: Cops don’t like have bosses constantly looking over their shoulders, and Shepherd didn’t want Hoke making decisions for him about the investigation.

Not long after Airhart slipped away, Hoke abruptly appeared. “Shep, what’s going on?” he asked. “You two having an argument?”

Shepherd denied it was an argument, but explained the gist of the conversation. “You’re stressed out,” Hoke replied. “I want you to go home for the next couple of days and take a rest.”

The message, Shepherd says, was clear: “We’re not going after white folk, was what he was telling me. Which we didn’t. So that was that.”

From there, the end came fast. When Walters brought in paperwork to renew the undercover operation — something the FBI required every six months — his boss called. “We’re gonna go ahead and close this down,” he told Walters. “You know, this is gonna be embarrassing enough for the police department as it is.”

Walters pushed back. “We can get a lot more officers, you know,” he said. But that went nowhere.

Still, Shepherd believes it was the Chicago PD that pulled the plug on Operation Broken Star, knowing that there were seven cops on the hook and that the investigation was on the verge of spilling over into multiple districts, which would have suggested a more systemic problem. By Shepherd’s count, they had identified between 35 and 40 cops potentially linked to Pacman’s group, many of whom were white. “We knew that Pacman had a little organization,” he says. “And it wasn’t just the few guys that we had.” He thinks that, at minimum, they could have netted another seven or eight officers.

Early on the morning of December 20, 1996, agents and police fanned out across Chicago. All seven of the accused cops were grabbed in their homes, except for one of the more peripheral figures, who surrendered that afternoon. The arrests made national news.

Walters and his FBI colleagues brought each cop into the federal building and placed them in separate interview rooms outfitted with TVs and video recorders. Walters went from room to room, revealing Silky’s identity and playing video they’d captured — after which he asked whether they were interested in talking.

The cops, who would become known as the “Austin 7,” had been caught stealing nearly $66,000, in amounts ranging from $500 to $25,000, over the course of a dozen encounters with Silky (a fraction, of course, of what they’d stolen over time). Drugs were found in the police lockers of four of the indicted officers, and investigators also found 11 guns in the officers’ homes; they suspected that some of them had been confiscated during investigations.

U.S. Magistrate Judge Rebecca Pallmeyer ordered four of the suspended officers — Pacman, Moore, Tripp and Lennon Shields — detained until trial, saying the charges against them “represent the grossest violation of the public trust that can be imagined.” Police Superintendent Matt Rodriguez called the seven cops “traitors to their professions” and “brazenly corrupt.” The Chicago Tribune described the affair as “one of the most notorious police corruption cases in Chicago history.”

In the coming weeks, Tripp and another officer eventually pleaded guilty and testified against the others.

After a jury found him guilty, Edward “Pacman” Jackson received a 115-year sentence. Moore was given 109 years. “These sentences are unbelievably tough because the crimes are so unbelievably terrible,” U.S. District Judge Charles Kocoras said.

After the trials ended, Shepherd was awarded the FBI Shield of Bravery, the highest honor given by the Bureau. An award from the Chicago PD arrived in the mail.

Operation Broken Star led to sweeping departmental changes. Chicago cops were forbidden from associating with gangs, and the city began scrutinizing the juvenile records of recruits for gang connections. Classes in the police academy put an increased emphasis on ethics and integrity. And applicants had to be at least 23 years old to apply and possess either two years of college or 60 hours of credits. A new commander was installed in the 15th District. “I want to restore the pride rightfully that our officers should have in themselves, and their department, and their city,” Superintendent Rodriguez said.

But Walters and Shepherd still feel the investigation didn’t go far enough.

Nearly a year after the case was shut down, Walters was home reading the Sunday Tribune when he came across an article that stopped him: An FBI agent had been arrested for allegedly stealing money from drug dealers. In one instance, the agent was accused of cooperating with a New Orleans drug dealer so he could rob others.

Walters froze when he saw the name: Daron Council — the New Orleans–based agent who had posed as Silky’s mule and spooked Shepherd with his behavior. Walters was stunned. (Council later plead guilty to accepting money from a dealer in exchange for information about narcotics operations. The other charges were dropped.) To Walters, it was more evidence that the crimes of Pacman and his crew were hardly isolated incidents.

Meanwhile, the Austin neighborhood has continued to struggle under the weight of painfully familiar urban American issues. When neighborhoods with boarded up storefronts slide into a pit of economic disadvantage, crime and systemic racism, the climb back is steep. In the clamor around the arrests, a TV news reporter interviewed Brad Cummings of the Austin Voice. “We don’t think that the department is ever going to be without corruption, or that the streets are ever going to be without gangsters and drug dealers,” Cummings said. “But we have to be able to depend upon the police to see what we see.”

Shepherd retired in 2000, having played his last undercover role. Walters remained in the FBI until 2012, working a variety of jobs, including with a surveillance squad and a unit whose members break into buildings — houses, businesses, hotel rooms and more — under court order to either put technology in or take something out.

Back in Austin, the cops played it straight, and the new leadership cracked down — at least for a time. But Chicago, like many big-city police departments, seems resigned to occasionally operating under a nimbus of scandal. There’s so much temptation. In 2011, a cop was nabbed for leading a corrupt group of officers and plotting to kill another cop. A year later, two Chicago police officers were arrested on charges of stealing $5,200 from an undercover informant whom they believed was transporting the cash for drug dealers. One of the cops had falsely planted drugs and guns on so many people that the city was forced to drop charges against 226 of them. And so on.

A quarter century after Operation Broken Star, Shepherd is still haunted by thoughts of how they were shut down too early. “I hoped that we would do the right thing, but you know how life is, especially in police departments,” he says. “It didn’t work out that way.”

Still. They had accomplished much against long odds, and for a while at least the people of Austin could walk the streets without being confronted by a rogue cop. “It was a good operation — fruitful,” Shepherd says. “And we got a few of the bad cops off the street for a while.”

David Howard is the author of two nonfiction books, most recently “Chasing Phil: The Adventures of Two Undercover Agents with the World’s Most Charming Con Man.”

Guang Lim is an award-winning illustrator and designer from Malaysia currently based in New York City. His illustrations deliver creative ideas and moods through the use of expressive strokes and shapes. Guang graduated from California College of the Arts in 2019.

Brendan Spiegel is Narratively’s Editorial Director and Co-founder.