Jack Riley says his goal is to disrupt the drug trade from Mexican cartels to street-level distributors: "This is the new face of organized crime."
Jack Riley says his goal is to disrupt the drug trade from Mexican cartels to street-level distributors: "This is the new face of organized crime." Credit: Jeffrey Marini

Even back in the late 80s, Jack Riley knew his job was about more than just drug busts. But he also found that a good bust was a thing to relish. In 1987 Chicago, like other American cities, was awash in cocaine from Central and South America, and sales of it had moved into the open. Residents of the west-side Austin neighborhood were complaining to the police that dealers had set up shop in and around the Washington Pines, a seven-story apartment hotel where men were seen hanging out in the lobby all day and night. Business was so brisk that neighbors had taken to calling the area “Crack City.”

Riley and his partner, William Maloney, were assigned to investigate. Both had been agents with the rapidly expanding Drug Enforcement Administration for only two years, but they were already experienced at staging stakeouts and working undercover. They had even developed an act: Riley, driving a white Mercedes with gold trim (which had been seized in the course of an earlier investigation), would pose as a yuppie college kid while Maloney acted as his cousin and handled the money as they made buys.

But the Austin case turned out to be more complicated than setting up a few deals. Riley and Maloney were watching the hotel closely, and it was soon clear that they couldn’t turn to the local cops for help—at least not all of them. Someone in the hotel was cutting and packaging shipments of cocaine and heroin, but they were moved elsewhere minutes before the arrival of Chicago police officers who were tipped off to them—a sure sign of leaks within the department. This wasn’t unusual. Through the 80s most narcotics in Chicago were sold by dealers tied to the Outfit, which in turn kept friendly police on its payroll.

Eventually Riley and Maloney tracked down an informant who knew the guys at the hotel. The informant, a character called Top Cat, had just been released from jail for failing to pay child support to one of his many girlfriends. He was fond of orange suits and stylish hats, and drove an old Lincoln Town Car; when he wanted to visit Riley and Maloney he’d just park the car on the sidewalk outside the federal building downtown.

Top Cat was an old acquaintance of the manager of the hotel, who happened to be an infamous police officer named Nedrick Miller. “He was the Outfit’s muscle in the black community,” Maloney says. “A lot of police officers liked him because if you had an issue on the west side he could fix it. You’d mention Rick Miller’s name [to cops], and if they hated him, they were straight. If they said, ‘Hey, Rick’s a good guy,’ you knew.”

Riley and Maloney received a warrant to tap the hotel’s phones, a practice that wasn’t widespread in drug investigations at the time. The DEA agents listened as Miller arranged purchases of cocaine and heroin from Mariano Lettieri, an Outfit-connected butcher who owned a shop a couple of blocks away. “So Rick would get on the phone and say, ‘Hey, I need a couple of rib eyes,'” Riley recalls. “Now, I’m not saying Rick didn’t eat rib eyes, because he was about 700 pounds. But they were talking about kilos of cocaine.”

Another DEA agent posed as a dealer named Little Wolf and approached the dirty cop at the apartment where he did business. “Rick actually sold him some drugs, and then he went back the second time and they had a card game going on there, and I think there were either five or six other policemen in the apartment in their uniforms,” Maloney says.

The agents determined that Miller’s hotel workers and street salesmen included three Cook County correctional officers as well as members of the Vice Lords street gang, among them Willie Lloyd, who would go on to become one of the most powerful drug and gang figures on the west side.

On April 20, 1989, more than 200 police and agents moved in on the hotel, arresting Miller and 18 others. But Riley and Maloney kept working up the chain. They received court permission to listen to the mobile phones of several suspected cocaine distributors tied to Miller—a groundbreaking technological development at the time.

In one of Jack Riley’s first big cases with the DEA in the 1980s, former Chicago police officer Nedrick Miller (left) was found to be overseeing a west-side drug operation tied to the Outfit. Among his workers was Willie Lloyd (right), who went on to become a leading gang figure.Credit: SUN-TIMES PRINT COLLECTION

It turned out that the men were underlings of a top mobster named Anthony “the Hat” Zizzo. One member of the operation was a Chicago police officer who made trips to Florida to pick up cocaine from a Colombian source. Others were also trafficking in stolen goods and overseeing gambling operations. Area business owners were told their legs would be broken if they didn’t cooperate.

In May 1990 the U.S. attorney’s office indicted nine of the Hat’s men for distributing cocaine. Riley was one of the star witnesses in the trials of both Nedrick Miller and the Outfit dealers. “It just showed you how nasty the underbelly was,” Riley says. “I think I aged about ten years in that case. But we were so into this—you didn’t want to take a day off. That’s how fun and exciting it was.”

It also left him believing that he was part of a bigger, more important fight, with nothing short of the security of the nation at stake. Riley began to understand the ways in which street dealers were working under other, more powerful figures—gang leaders, organized crime networks, and international traffickers who were in it to make a stunning profit, no matter how much devastation it brought on communities like Austin. As a law enforcement official, stopping the destruction meant working up the chain.

As Maloney remembers it, Riley vowed that he was in it for the long haul, with a specific goal in mind. “He says, ‘I want to be back here and be the agent in charge of the DEA here in Chicago.'”

In 2010—after a quarter century as a DEA agent—Riley got his wish. He was tapped to lead the agency’s Chicago division, overseeing operations from North Dakota to Indiana. By most measures, it’s one of the toughest jobs in federal law enforcement.

The city of Chicago has led the country in murders for the last two years, outpacing its larger rivals, New York and Los Angeles. The daily bloodshed is fueled at least in part by a drug trade that’s replaced the legal economy in many neighborhoods where disputes are settled with guns.

While the demand for powder and crack cocaine has decreased, the heroin trade has grown. Thanks to its “logistical advantages”—its rail, air, and highway networks—Chicago is a hub for heroin trafficked from Mexico by cartels, distributed to street gangs in the city, and eventually dispensed to customers from Vermont to Missouri. “It’s a great place to do business, and unfortunately that’s true for the bad guys too,” Riley says.

The metropolitan area is the national leader in the rate and total number of heroin overdoses. The supply is so ample that prices are lower here than anywhere else except Detroit.

“Virtually every trafficking case we dealt with crossing the border had something to do with the midwest, and Chicago was the center of it. Money flowing down, dope going up. I thought to myself, ‘This is what we’re missing.'”—Jack Riley, special agent in charge of the DEA’s Chicago division

“That’s why I look like this,” Riley jokes. Now 56, Riley keeps his white hair cropped short, and his ruddy face is punctuated by crescent bags under his eyes. But it’s clear he views his job as a calling. He’s fond of telling stories over a pint or two about his life’s work, whether they’re about Mexican cartels shipping heroin north in trucks of chile peppers or the time he was doing undercover surveillance on the west side and a homeless man walked up to his car, dropped his pants, and defecated on the hood. It’s not a coincidence that these tales usually feature colorful characters, one of his own miscues, or, especially, a dumb slipup by a criminal who thought himself invincible. In this work, Riley finds it essential to keep himself and everybody around him loose.

Since becoming the special agent in charge in Chicago, Riley’s intensity and charisma have made him one of the most quoted and recognizable advocates for drug enforcement in the country. What he does while in this role will affect the future not just of Chicago but of drug policy in a larger, philosophical sense. If he has his way, he and his agency will lead the effort to break down the international drug trade—both by weakening the Sinaloa cartel while its leader, El Chapo Guzmán, is prosecuted, and by dismantling the criminal organizations operating in some of America’s most troubled neighborhoods. “I don’t want to sound like an old cold warrior, but I think that this goes to the heart of what America is about,” he says. “This is good versus evil.”

Heroin use and overdoses were soaring nationally by the time Richard Nixon created the DEA in 1972 with a vow to fight traffickers as well as street distributors. Two years later, the top DEA official in the midwest told the Tribune that Chicago’s role as a transportation center had turned it into the nation’s “hub” for trafficking heroin.

The next DEA chief tried to clarify the agency’s role. “I want to get away from having a number of arrests simply for the sake of statistics,” Peter Bensinger, a Chicago native, told reporters upon his appointment in 1976. “Our effort will not be on the street dealer but on the financier, importer, the criminal organization leader or leaders.”

Heroin use dropped in the late 1970s. But Americans developed an appetite for cocaine, and Latin American suppliers happily obliged by channeling their products through south Florida. After President Reagan declared another war on drugs in 1982, authorities poured resources into thwarting the cocaine trade. In 1980 the DEA had about 1,900 special agents and a $207 million annual budget. By 1994 it had 3,400 special agents and a $1 billion annual budget.

Riley grew up in the south suburbs, one of three kids. His mother was a homemaker and, by his account, “the life of the party,” while his father was a doctor who’d attended Notre Dame on the GI bill, leaving Riley with a lifelong devotion to the Fighting Irish. He was also riveted by stories about his grandfather, a Chicago cop who’d worked in the vice districts just outside the Loop. “He was a hard Irish guy who loved his city and loved the police department, but I think he was a son of a bitch. They said he had fists as big as a table, and I’m told he laid them on some people.”

After high school Riley went to Bradley University with the hope of walking onto the basketball team. “They wouldn’t let me in the gym, I was so bad,” he says. He focused on having a good time, and by graduation he still had no idea what he wanted to do with his life. With a general interest in government and public service, he enrolled at the University of Illinois Springfield to pursue his master’s in public administration. One of his classmates was a DEA agent, and Riley was immediately intrigued by tales of the agency’s investigative work. “The DEA was under the radar—that was before the Miami Vice days—and it sounded like a really good time to be on the job, because everyone stayed out of your way,” he recalls. Riley submitted an application, and six months later completed the screening process. He started his career in Chicago in 1985.

There were relatively few regulations in place for DEA agents, meaning even rookies were given the latitude to improvise along the way. “We just were running by the seat of our pants half the time—we didn’t have much supervision back then,” recalls Maloney, who was Riley’s first DEA partner.

Maloney’s father, a veteran Chicago police officer, put the two in touch with some street informants, and they developed their act for making undercover buys as yuppies. “We did some crazy stuff—just unbelievably stupid and crazy,” Riley says. One of their scares came in 1987, when they nabbed a cocaine buyer in the western suburbs who agreed to help them snare his suppliers—members of the Brothers motorcycle gang. After a series of smaller buys, Riley and Maloney went to a high-rise apartment in suburban Addison to negotiate a $175,000 deal. They quickly realized the apartment was out of the sight and sound of other agents who were providing backup, and Riley wasn’t wearing a wire. He decided to go ahead anyway.

As soon as Riley stepped into the apartment, one of the gang members grabbed his bag and found his gun. He accused Riley of being a fed. Riley denied it. “This goes on for 20 minutes,” he says. “I knew there was about a 30-minute limit before [other agents] came up and they were going to knock the door down, and I’m beginning to think I’m not getting out of this. So I say, ‘Come down and see the money.'”

Finally they agreed. Riley showed them the cash, and the gang members agreed to bring the cocaine to the parking lot of a pizzeria that night. When the coke arrived around 11 PM, other agents and police swarmed the scene and placed the bikers under arrest.

Riley and Maloney suspected that the gang had a connection to Colombian suppliers, but they were never able to prove it.

By the mid-90s the federal government had mobilized enough land, air, and sea forces that smuggling drugs through the Caribbean and south Florida became difficult and prohibitively expensive. So Colombian cartels began working with Mexican drug organizations that would move their shipments across the open border.

Riley, meanwhile, was promoted. In 1998, as the stream of drugs across the border was building, he was assigned to the agency’s special operations division in Washington to investigate Mexican drug organizations.

Veteran DEA agent Jack Riley says the captures of Sinaloa cartel leader Chapo Guzmán (left) and top deputy Jesus Vicente Zambada-Niebla (right) offer an opportunity to weaken drug trafficking networks, but police don’t believe it will make a difference on the streets of Chicago.Credit: ALFREDO ESTRELLA/AFP/Getty Images; LUIS ACOSTA/AFP/Getty Images

That’s when he first took notice of Joaquín Guzmán Loera, otherwise known as “el Chapo.” Despite being incarcerated in Mexico, Guzmán was a logistical expert for the Sinaloa cartel as it fought for a bigger share of the American drug market. “He was showing up all over the place,” Riley says. “I always thought, ‘We’ve got to go after this guy if we’re going to disrupt the company.'” Riley and other DEA officials thought about how earlier federal investigations had broken down the Outfit over time—and concluded that the same strategy could work with the Mexican cartels.

In 2001 Guzmán escaped from a Mexican prison with the help of his guards, reportedly hiding in a basket of dirty laundry. He went into hiding and from there led the Sinaloa cartel to its dominant position in the worldwide drug trade, with networks in the United States, Europe, and Africa.

Riley, meanwhile, spent seven years as a supervisor in Saint Louis before being named the special agent in charge of the DEA’s El Paso division in 2007. He would be responsible for southwestern Texas and all of New Mexico, including a third of the Mexican border.

His arrival late that year coincided with an explosion of violence on the other side of the Rio Grande. In 2007 Juarez—a city of about 1.5 million people, half the size of Chicago—reported 320 murders. In 2008, as Sinaloa cartel members fought for control of the city with the Juarez cartel and other gangs, the homicide toll soared to 1,623—and then to 3,622 by 2010. There were concerns that the violence would spill into the U.S.

In a newspaper interview after he started the new position, Riley declared his intention to go after the cartels. “They might already know who I am, and we know who they are,” he told the El Paso Times. The cartels did know. Soon after, Mexican authorities conducting wiretap surveillance heard a cartel associate say, “How much do you think they would give me for killing Riley and cutting his head off?”

Riley downplayed the news, saying it “surprised me because I didn’t think they could read.”

He tried to focus the DEA’s efforts on the cartels. Conceding that his agents couldn’t investigate every case of drugs seized at the border, he took aim at midlevel players, “the operational guys, the ones who call the shots daily,” who might lead them higher up the pyramid.

“The problem with El Paso is that none of the dope really stays there,” Riley says. “Virtually every trafficking case we dealt with crossing the border had something to do with the midwest, and Chicago was the center of it. Money flowing down, dope going up. I thought to myself, ‘This is what we’re missing.'”

There was another widely watched development while Riley was in El Paso. Breaking Bad was in production, and Riley went on the set several times at the invitation of Vince Gilligan, the show’s creator. Riley says it was largely an accurate portrayal of the meth business in New Mexico, though the show may have even understated the violence. Riley also found plenty to like in Hank, the DEA agent, saying he was hardworking and “matured as an agent throughout the show.”

In 2010, when Riley was tapped to lead the DEA’s Chicago division, close observers saw it as an acknowledgment of the growing ties between Mexican cartels and the drug business in Chicago. The connections were already being spelled out in federal court. In March 2009 Mexican authorities arrested Jesus Vicente Zambada-Niebla, the son of Chapo Guzmán’s top lieutenant and a high-ranking Sinaloa operative in his own right.

A month later federal prosecutors in Chicago indicted Zambada-Niebla, his father, Guzmán, and several associates, charging that they had arranged to have cocaine brought into Mexico from Colombia and Panama, and then had hired a pair of brothers in the Chicago area to distribute cocaine as well as heroin.

Initially Zambada-Niebla’s attorneys argued that he and his Sinaloa associates had been operating with the consent of the U.S. government in return for providing information about rivals. The U.S. government denied the claim.

Zambada-Niebla was brought to Chicago to await trial, then moved to Michigan as a protective measure. Riley was among the authorities who interviewed him. Riley says he was furious about all the deaths Sinaloa was responsible for. “But he was respectful to me,” Riley says of Zambada-Niebla. “He grew up in a military-style organization.”

Publicly, Riley used the opportunity of the high-profile arrest to emphasize the threat posed by the cartels: “We’re 1,800, 2,000 miles off the border, but don’t think that that’s not your problem.”

He and other officials successfully lobbied the Justice Department for about $1 million to set up a strike force—a team drawn from numerous federal agencies and local and state police departments, housed in a renovated warehouse just outside the Loop.

In February 2013 the Chicago Crime Commission, a nonprofit civic organization, took Riley’s message to a dramatic new level by naming Guzmán Chicago’s public enemy number one—the first person to earn that designation since Al Capone. “We know that, for the most part, the gangs make their money, fight over their turf, shoot each other in defense of the drug trade,” Riley said at the announcement. “And we do know that Chapo Guzmán and Sinaloa supply the majority of narcotics available to the city and to the region.”

One morning last August, Riley put on a tie and carried his DEA windbreaker—which he prefers to a sport jacket—as he hurried into the DuPage County courthouse in west-suburban Wheaton. As he stepped into an elevator with several suburban police officials, one of the men turned shyly to Riley. “You probably get this all the time, but my wife’s got me watching this show, Breaking Bad—”

Riley didn’t need to hear the question. “I was the special agent in charge on the border when that show started,” he said. “We actually went on the set.”

“I wouldn’t think I’d like it, given the subject,” said the officer. “But I have to say, it’s a good show.”

In a few minutes they sat around a conference table with DuPage County state’s attorney Robert Berlin and went over the case they were about to announce to the public: 25 suspects were in custody after a six-month investigation into a heroin ring by the DEA, the DuPage state’s attorney’s office, the state police, and several local departments.

Berlin asked if anyone knew the whereabouts of two of the suspects who hadn’t been rounded up yet. One of the other DEA agents—a medium-built man wearing a wide brown tie—reported that their phones were still being tracked, and the first suspect was driving a truck somewhere in Georgia. He added: “One of the phones we seized was getting calls yesterday from Mexico.”

“That’s what I like to hear,” Riley said. He looked quizzically at the agent. “Nice tie you got there. You get that from a search warrant in the 70s?”

Five TV cameras and half a dozen reporters were waiting in the press room downstairs. Berlin told them authorities had uncovered a heroin operation based on Chicago’s northwest side; customers would call in orders that were filled by runners making deliveries or arranging meetups. The business brought in as much as $3,000 a day.

Berlin noted that in the previous 20 months, 70 people in DuPage County had died from overdosing on heroin. “We have a heroin epidemic,” he said.

Riley stepped to the podium and delivered his trademark message. “This is a great day for the good guys in this county,” he said. “This is the way we’re going to do business from this day forward. We’re going after organizations, from the people bringing it in to the people putting it on the street.” He added: “This is the new face of organized crime.”

Though the faces, names, and techniques of his targets are different than they were 30 years ago, Jack Riley admits that the drug business remains strong. “The game hasn’t changed a lot.”Credit: Jeffrey Marini

Peter Bensinger, the DEA head from 1976 to 1981, says Riley’s approach has been “very effective.”

“People like Jack Riley are going to make it harder for the traffickers to make it available,” Bensinger says.

Yet the drugs keep arriving, and the cost of policies to stop or slow them keeps climbing. The DEA’s annual budget now exceeds $2 billion.

The number of defendants detained in the war on drugs keeps growing as well—with no end in sight. More than 215,000 people are locked up in federal prisons, about half for drug offenses, and the population is expected to continue to swell. Another 400,000 drug offenders are in state prisons and local jails. The federal prison system alone costs more than $6.5 billion a year.

Yet few of those hauled into federal court are “at the top of the pyramid,” notes Beth Jantz, an attorney for the federal public defender’s office in Chicago.

“They’re not making much money, maybe a couple hundred dollars on the deals,” she says of the average federal inmate. “They’re not organizing or making decisions, and they can’t offer much to the authorities.”

Jantz argues that locking up these dealers doesn’t address the larger issues of drug abuse and economic opportunity. At the very least, she says, enforcement and sentencing should be based on the offenders’ leadership roles rather than metrics like the volume of drugs they handled.

The idea is catching on. In March, U.S. attorney general Eric Holder—the figure Riley ultimately reports to—announced that he backs lighter prison sentences for nonviolent drug offenders. And both Holder and President Obama have signaled that they’re not going to stop marijuana legalization in Colorado and Washington.

Riley responds to these developments with a mix of resignation and frustration. “I’m employed to enforce the laws until the policy makers change them,” he says. “Sometimes I’d like to say what I think, but I’ve got to do my job.”

Still, he predicts that legalizing marijuana won’t eliminate the black market, because someone will try to offer products below the price of regulated pot. And he’s concerned that Illinois won’t even be able to control its slowly unfolding medical marijuana program. “This is a state that can’t even get video poker straight, and they’re talking about a substance that kills people?”

Kills people?

When pressed, Riley won’t reiterate the claim—but he says he does believe that smoking pot can lead to abusing harder drugs, including heroin. The so-called gateway theory has been debunked by studies; most weed smokers never try cocaine or heroin.

“That’s the argument, but I don’t see those people,” Riley says. “I see the other side.”

He tells a story about meeting the parents of an Iraq war veteran who came home and overdosed on heroin. “Your son’s a hero and we can’t control heroin? That’s the shit I see.”

In February Chapo Guzmán was captured without a fight after a raid in Mazatlán, Mexico. Several sources have suggested that intelligence from Guzmán’s connections in Chicago was instrumental in tracking him down.

The Justice Department won’t let Riley comment on the case. He’ll only describe how he felt when he received the news: “I’m the starting quarterback for the Fighting Irish, we’re playing in the national championship game, and I just threw a touchdown in the fourth quarter and we won.”

Riley has always argued that Guzmán’s capture could cause disruptions in the international drug trade that make the Sinaloa cartel vulnerable. But when I asked a veteran Chicago narcotics officer what impact it would have on the day-to-day business here, he didn’t hesitate. “On the street, the only thing that’s really going to happen is absolutely nothing,” he said. “As long as there’s a demand, there will be a supply. They’re trying to use him as an example—for PR.”

Riley agrees that Guzmán was a symbol and that he can be replaced. “What he represents is really the dominance of Mexican organized crime in the midwest and the importance of this city,” he says. “I think that’s what people want. They want to know what evil is.”

In early April officials revealed in an unsealed court document that Zambada-Niebla agreed last year to plead guilty to distributing cocaine and heroin and is cooperating with authorities investigating his father and El Chapo’s organization. At least one other Sinaloa operative has pleaded guilty in federal court in Chicago in recent weeks, and others are in custody.

Riley himself faces mandatory retirement next year, but he’ll say only that his work isn’t winding down—far from it—and neither is the drug business. “We talk about a Gangster Disciple guy being an unwitting contractor for Guzmán—well, Anthony “the Hat” Zizzo, Mario Lettieri, and Rick Miller did the same thing. They never thought of themselves that way, but they were dealing with a foreign entity that didn’t care about who died. The game hasn’t changed a lot.

“Let’s be honest—we’re going to be grappling with this for the rest of our existence. We’ve been fighting and fighting to stop murder, and we’re not giving up. I think that’s what narcotics trafficking is about.”

Mac Irvine and Jillian Sandler helped research this story.