After El Chapo

Federal prosecutor Tom Shakeshaft ’89 helped take down one of the world’s most notorious drug lords. Now he’s fighting to recover from the aftermath.

Twelve years ago, Tom Shakeshaft flew to Monterrey, Mexico, to meet with a high-level drug dealer. Before that fraught encounter, which contributed a decade later to the conviction of drug czar Joaquin “El Chapo” Guzman, he wrote a letter to his wife. In it he told her how much he loved her. He acknowledged his mission involved danger, but as the lead prosecutor on a potentially crucial drug investigation, he told her he felt a sense of duty. Even with a wife and newborn, he couldn’t ask someone else to go in his place. 

Shakeshaft sealed the letter, wrote his wife’s name on the envelope and closed it in the top drawer of his desk at the U.S. attorney’s office in Chicago. He told one colleague about the letter. “This could go badly,” the man said of the trip. “It’s like sliding into Hitler’s Germany.”

“If something bad happens, just make sure she gets it,” Shakeshaft said.

Shakeshaft survived the trip without being gunned down in a flurry of drug violence, but it led to him facing another insidious danger. He spent the next seven anxious years shepherding a sprawling drug prosecution that drove him into heavy drinking. By the time of El Chapo’s conviction in a federal court in Brooklyn in February 2019, Shakeshaft had been in and out of rehab. He was living alone, practicing law by himself, seeing his young kids only after being cleared by Soberlink, a remote breathalyzer device.

Shakeshaft, 53, today says his journey was worth it. El Chapo now languishes in a federal prison in Colorado—“under a mountain,” as Shakeshaft puts it—and the investigation Shakeshaft ran brought down the biggest drug operation in Chicago history. “The one thing I lost out of all this is my marriage, and I loved my wife,” he says. The divorce counts as “one of my largest regrets in the world.” But, he adds, “I’m a Teddy Roosevelt, man-in-the-arena guy. I would rather have gotten a bullet in the head in Monterrey than not have gone.”

Shakeshaft was working in narcotics as an assistant U.S. attorney in 2007 when a garden-variety drug bust on Chicago’s West Side led to the arrest of a 340-pound dealer who went by the street name “Fat Mike.” In a meeting the next day, Shakeshaft asked Fat Mike who supplied him. “The twins,” he replied.

Drug insiders knew the twins—Pedro and Margarito Flores, a matching pair of young Mexican Americans who had created a huge drug-trafficking operation with a distribution network that stretched across the country. They’d grown up bilingual in a Hispanic neighborhood of Chicago, the sons of a small-time dealer. Though still in their 20s, they’d built an astonishing business infrastructure, including a fleet of semi-trailers with hidden compartments on their roofs, above the sniffing range of dogs trained to smell drugs. Under the guise of a legitimate shipment of, say, produce, the twins shipped heroin and cocaine to Chicago on the top of a truck and sent cash back to Mexico the same way. The money involved was staggering: Between 2005 and 2008 the twins moved $1.8 billion in drug money from the United States to Mexico, according to the U.S. attorney’s office for the Northern District of Illinois. 

Already facing indictment in Milwaukee, the Flores twins had fled several years before to Guadalajara, Mexico, where they were living lavishly with their wives and children while running their operation through Chicago. The twins acquired the drugs on consignment from a federation of Mexican traffickers, chiefly the Sinaloa Cartel, headed by the savage kingpin El Chapo. In the course of doing business, the brothers had come to know El Chapo. They had even visited him at his mountain hideaway. 

Not long after the arrest of Fat Mike, a Chicago lawyer asked to meet Shakeshaft in his office in the federal building. “I have a proposal for you,” the man said, after closing the door. “I have two clients who live in Mexico.” The cartel federation had cracked. Two of the cartels supplying the twins had each issued an ultimatum: Deal our dope and only our dope or else. “My clients don’t think that’s going to end very well for them,” the lawyer said, “and they would like to explore the possibility of cooperating with the United States.” 

“You have my attention,” Shakeshaft told him. The Sinaloa Cartel stood at the pinnacle of a multibillion-dollar, international drug-trafficking business with tentacles throughout the Mexican government. “We all of a sudden had a case that went right to the top of the cartel food chain—it went to Chapo himself,” says Shakeshaft.

Arranging the complex logistics of a meeting with the twins took several months. Because of the existing indictment, they couldn’t come to the United States, so the meeting would be in Mexico. The DEA, the FBI, and the U.S. Diplomatic Security Service all had a hand. The Mexican government couldn’t know—given El Chapo’s network, someone could tip him off. For the visit, Shakeshaft had to pretend he was a tourist. 

The meeting was set for November 6, 2008, in Monterrey, a city outside Sinaloa territory in a region controlled by a rival cartel. One of the twins, Pedro, would attend along with his lawyer. The day before leaving, Shakeshaft wrote the letter to his wife. “I wasn’t worried that I was going to get killed because I was me,” he says, “but when you’re meeting with a cartel member in Mexico, it’s the crossfire, it’s the inadvertent.” Pedro Flores was also at great risk. “Cartel guys are watched, not so much by the Mexican government but by rival cartels and their own cartels.” Being spotted talking to an American official would amount to a death sentence. 


(Illustration by P.J. Loughran)

The actual trip featured scenes that could have been lifted from Homeland. In Monterrey an armored SUV met Shakeshaft at the airport and the next day carried him to the American consulate. A squad of agents armed to the hilt waited behind a huge steel door. “It’s a f***ing armory,” Shakeshaft recalls thinking. “I am sitting there scared out of my mind and I’m running the show.” The American team loaded up in a convoy of SUVs and roared around the streets of Monterrey to make sure they weren’t being followed before ending up at a Radisson hotel.

The twins’ lawyer had flown separately to Monterrey and was with Pedro Flores. Following plans, an agent called the lawyer from a hotel room and told him to be there with his client in 20 minutes. Shortly after, the dealer walked in. “He’s wearing a polo sweater,” Shakeshaft recalls. “He could have been any young [man], really young. I introduce myself, ‘Tom Shakeshaft, I’m from the U.S. attorney’s office in Chicago.’ He said, ‘I’m Pedro Flores.’ ”

Through the course of the day, Flores provided an overview of the twins’ operation. Under the terms of the cooperation agreement, they would keep running the business from Mexico, helping to gather evidence. Shakeshaft was back on a plane to Chicago that night, “feeling absolute relief,” he recalls.

For a month the twins continued making deals, recording scores of conversations. The most significant were with El Chapo himself, including the first recorded conversation to place the drug kingpin in the middle of a deal. “It was the single biggest piece of evidence in the entire case,” says David Lorino, the DEA agent in charge of the Chicago investigation. Meantime, agents seized almost all the twins’ dope coming into the United States, obviously limiting the lifespan of the subterfuge. Shakeshaft and Lorino were working one Sunday when it became clear El Chapo would soon know the twins had betrayed him. The prosecutors needed the brothers alive to back up the recordings. “If Pedro and Margarito are killed, we got no case on anybody,” Shakeshaft says.

The Americans had the twins flown out that day, while their families left almost immediately for the States in a caravan of Range Rovers and then scattered across the country. Back in the States, the twins pretended to deal, gathering evidence against their network of distributors. Once the operation finally shut down, Shakeshaft and his colleagues spent years deciphering the tapes and making cases. 

Meanwhile, the pressure increased on Shakeshaft. For their protection, the twins were regularly moved from one Midwestern lockup to another. When their father defied warnings and returned to Mexico, abductors grabbed him at a pool hall and left a note on his car, a message for the twins: “Tell those f***ers to shut up or we’ll send you his head.” Shakeshaft had to break the news to the brothers. The father is presumed dead. “My adversary was the most murderous human being on the face of the planet,” Shakeshaft says of El Chapo. “I woke up every morning like, ‘Jesus Christ. God, help me get through this thing.’” 

“My adversary was the most murderous human being on the face of the planet. I woke up every morning like, ‘Jesus Christ. God, help me get through this thing.’ ” 

Lorino, the DEA agent, says, “Tom internalized a lot of what was happening out on the street on himself, [worrying] about whether somebody was going to get hurt because of a decision.”

Patrick Radden Keefe, a New Yorker writer who has reported extensively on El Chapo, interviewed Shakeshaft for a 2016 New Yorker podcast that featured the Chicago investigation. The two became friends. “I think if you listen to that [podcast] you can hear—it’s not a word I throw around—but you can hear some of the residual trauma in his voice from that experience,” Keefe says.

The intense story of the drug investigation inevitably folds into the story of Shakeshaft’s alcohol abuse, and some of his pain seems to spring from his surprise at how things have turned out. He came to Dartmouth from Ames, Iowa, in 1985 as a standout athlete. After quarterbacking the freshman football team, he competed for the starting QB role through two varsity seasons. “Tom was very thoughtful, very receptive, very competitive, and just a highly intelligent guy,” says Buddy Teevens ’79, who arrived for his first stretch as Dartmouth head football coach when Shakeshaft was a junior. The two have remained in touch. 

Although his 6-1 frame has puffed out somewhat, Shakeshaft still carries himself with the assurance of an athlete. “The reason I became a trial lawyer was I tried to find the closest thing in the professional world that approximated competitive athletics,” he says.

After the University of Iowa Law School and a federal clerkship, he worked for Cravath, Swaine & Moore in New York City and made partner at McDermott, Will & Emery in Chicago. In 2004 he joined the U.S. attorney’s office for the Northern District of Illinois. He took a pay cut of several hundred thousand dollars, but he carried a strong commitment to public service instilled by his father, who had earned a Silver Star in the Battle of the Bulge and became a beloved political science professor at Iowa State. 

By then, Shakeshaft was dating the woman who would become his wife. (She declined to comment for this story and asked that her name not be used.) They married in 2006, and their first child was born two years later. 

During the investigation, Shakeshaft reasoned that there was relatively little risk to himself or his family, which in 2010 grew to three children with the birth of twins. He assumed the cartels wouldn’t go after a federal prosecutor or agent because the response would seriously upend business. Still, when the Department of Justice arranged to install a security system in the house of Shakeshaft’s boss, U.S. Attorney Patrick Fitzgerald, who had been deeply involved in Al Qaeda cases, Fitzgerald ordered a system for Shakeshaft’s house, too. The equipment amounted to a regular ADT electronic security system, wired to alert both ADT and the U.S. Marshals Service.

Not long after, several marshals visited the Shakeshaft house to inspect the installation. One ran through standard security advice for Shakeshaft’s wife: Don’t take your kids on a walk in the same direction at the same time on consecutive days. “You could have seen the fire come out of her eyes,” Shakeshaft recalls.

As both a private lawyer and a prosecutor, Shakeshaft had enjoyed consistent success, never losing a case. Still, he couldn’t shake a growing fear of failure. Through the Flores twins’ investigation, he was overseeing several dozen cases involving 62 defendants, including El Chapo. “It was very complex, it was really stressful, and you had to be in nine different places at one time,” Shakeshaft recalls. At one point, referring to the twins’ investigation, Patrick Fitzgerald told him, “This is the most important case in the country. We can’t f*** it up.”

Shakeshaft often worked late nights and weekends. He was virtually absent from home, where he says his wife was coping with three small children. Because of concerns for secrecy, almost the only people Shakeshaft could talk to about the investigation were fellow prosecutors and federal agents. Many evenings he and colleagues would gather at a favorite bar near the federal building. “It was the one time I could shut my brain off for a little bit.” At first he mostly drank beer or wine. “And then at some point it turned to Scotch. That’s sort of when it became a problem.” 

By Shakeshaft’s account, he basically held things together until the spring of 2014, when he handled a guilty plea in one of the last Chicago-based cases to come out of the investigation. He thought once his role ended, the stress would pass and he would return to normal. Early the next year, he left the U.S. attorney’s office for a big Chicago firm, but the work he expected to do for a major corporate client never materialized. And it turned out he’d triggered a habit he now couldn’t throttle. He went through several rehabs, but each time fell back. 

He says his wife grew worried about the impact on their children. He devised schemes to hide his problem. “I had all the same gimmicks as the other guys. Mine was to put little red wine bottles in my golf bag in the garage. And so after dinner I’d say, ‘I’ll go park the car.’ ” Finally, in October 2016, he says, his wife told him to move out.

Shakeshaft acknowledges that he can’t simply blame his problem on his former job. Alcoholism runs through his family. Shakeshaft says that at some point in his life something stressful would have driven him to find solace in alcohol. “It’s in my heredity.” 

The Justice Department consolidated nearly a dozen El Chapo indictments around the country into a single prosecution in the Eastern District of New York. In December 2018, Pedro Flores appeared as a government witness. During two days, Flores, then 37, testified that he had sold about 38 tons of drugs for El Chapo. Jurors listened to the recordings of conversations between the two men. Flores was one of more than a dozen prosecution witnesses with inside knowledge of the cartel, but his testimony came up repeatedly in Assistant U.S. Attorney Andrea Goldbarg’s closing argument. The jury convicted El Chapo on all 10 counts, and the judge sent him away for life. 

The Justice Department views the investigation that started with a minor drug deal on Chicago’s West Side as a success. Of the 62 people indicted under Shakeshaft’s watch, 58 were convicted. The other four are either dead or on the run. 

Shakeshaft doesn’t pretend that El Chapo’s conviction comes close to squelching the drug trade. The Sinaloa Cartel continues to send drugs into the United States, reportedly with Chapo’s sons taking a growing role in the business. So what’s the point? “It certainly can lead to the feeling that we were playing whack-a-mole,” Shakeshaft says. “But the flipside to that question is what’s the alternative? Just give up?” 

These days Shakeshaft has his own quiet practice, but he is looking to sign on with a Chicago firm. He says he’s not concerned about the stress of big cases—he knows he’s better when he’s working hard. He admits that he has struggled even recently to stop drinking. “My biggest times are when I’m alone or feeling useless, which makes the last couple of years pretty tough,” he says. As of this writing, he thinks he’s made it, pushed by his commitment to his children and the physical pain of withdrawal. “My body is telling my brain, ‘You can’t do that anymore.’ ” He lives in a tiny house just down the street from his family and breathes into Soberlink 90 minutes before he picks up his kids. His ex-wife gets the report immediately. Then he’ll breathe into the device several times when they are with him. His Jeep has a breathalyzer ignition device. Alcohol, he says, “just messed up my life.”

Keefe, the New Yorker writer, says Shakeshaft’s decision to come forward about his drinking problem is brave. “He has a sort of warts-and-all candor about his own life and experience,” he says.

Buddy Teevens puts it this way: “He takes ownership.”

Shakeshaft says it is possible to come out on the other side. He maintains that he’s “weathered the storm. Certainly, I did not weather it like a champion, but if this were a disease that were that easy, you would just snap your fingers and say, ‘Oh, okay, I’m done.’ It doesn’t work that way. And so I have taken seriously my responsibilities to my children, to my—to use a technical term they use in AA—my fellow sufferers, to my community, and to everybody else. And to my country. That’s why I did all this stuff.”   

Richard Babcock, the former editor of Chicago magazine, is a novelist and teaches journalism at Northwestern University. 


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