One of the biggest drug investigations in history began in Chicago with less than two ounces of heroin.

On a hot summer day in 2007, a west suburban drug dealer named Christopher Baines sold a plastic baggie containing 50 grams of the brown, powdery stuff to a government informant near Cicero and Chicago avenues on Chicago’s West Side. 

It was a modest, street-level deal. The buyer paid Baines $5,000. After three more sales to informants, Baines was busted for drug-trafficking. 

Cases like these happen all the time in Chicago. Only this time, it ended up leading to Mexican drug kingpin Joaquín “El Chapo” Guzmán Loera, the world’s most-wanted criminal, court records and Chicago Sun-Times interviews with key players in the investigation show.

The arrest of El Chapo by Mexican marines near the coastal city of Los Mochis in Sinaloa in January 2016 already is the stuff of legend, with his unsuccessful escape through stinking sewers following a series of failed raids on his properties, one of them after a clandestine meeting with actor Sean Penn.

Authorities have never revealed that the case against the man who some believe was the biggest drug kingpin in the world began with Baines, a mid-level dealer whose father owned a grocery store in Austin and also drove a bus for the CTA.

But a Sun-Times review of court records and interviews with Baines and others involved in the case, including a key former federal prosecutor, has found that a Drug Enforcement Administration task force used a web of informants and hundreds of wiretapped calls to trace a path that ultimately led from Baines to El Chapo.

“We went from the streets of Chicago to the mountaintops of Mexico,” says Thomas Shakeshaft, a former assistant U.S. attorney who supervised each phase of the investigation. “We started a case against the Traveling Vice Lords on the West Side of Chicago and went all the way up.

“Before Sean Penn flew down to Mexico with [actress] Kate del Castillo and recorded this thing where Chapo admitted he was the largest drug-trafficker in the world, we had the only legally admissible voice recording of Chapo in the world.”

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Shakeshaft credits “a combination of hard work, the resources of the U.S. government and luck.”

The El Chapo case was the highlight of Shakeshaft’s career as a prosecutor. And it exacted an enormous toll. He says the pressure of keeping witnesses alive while overseeing an international drug investigation drove him to drink and led to a diagnosis of post-traumatic stress disorder.

And Baines’ case, he says, sparked all of it.

Thomas Shakeshaft is the former assistant U.S. attorney who handled every step of the investigations of Chris Baines, the Flores twins who were Chicago’s biggest drug dealers and Mexican drug kingpin Joaquín “El Chapo” Guzmán Loera. | Rich Hein / Sun-Times

THE INITIAL ‘BUY’

Once listed by Fortune magazine on its roster of billionaires, El Chapo had been charged in 1995 with drug conspiracy in San Diego. But the Chicago investigation led to some of the most damaging evidence against the security-obsessed druglord: a recording of Guzman negotiating a deal, according to Shakeshaft and high-level government officials.

El Chapo was indicted in Chicago in 2009. At the time, federal prosecutors said he exported tons of drugs to the United States via ships and submarines and 747s.

That case sprang from the 13-month investigation that led to Baines’ arrest, according to Shakeshaft.

“Chris Baines was known to DEA as a Traveling Vice Lord — not necessarily a full-on member of the gang — but he was a significant narcotics trafficker on the West Side and lived in Maywood,” Shakeshaft says. “And, like a lot of these cases, DEA got started looking at somebody that they know about. And the case agent had a cooperating source who could buy into Baines. And that’s how we work these things.”

The first “buy” was on July 3, 2007. Baines and his cousin Charles Parker sold 50 grams of heroin — less than a cup — to a man with a disturbing rap sheet, including an arrest for murder. The customer was paid at least $3,500 by the DEA to be an informant against Baines, court records show.

The informant hopped in Baines’ Chevy Tahoe outside a currency exchange in Maywood. After paying Baines $5,000 in money provided by investigators, the informant drove to a home near Cicero and Chicago avenues on the West Side where Baines’ cousin got in the car and placed the drugs in the cup-holder, records show.

Baines, known as “West Side,” offered to put him on his “team” of dealers, the informant told the DEA.

Baines and his associates sold similar amounts of heroin to informants three other times, records show.

In July 2008, a DEA task force — federal agents, Chicago Police Department investigators and members of other law-enforcement agencies — arrested Baines.

He wouldn’t talk. But one of his friends, a higher-level dealer named Michael “Fat Mike” King, agreed to cooperate.

King’s suppliers were Pedro “Peter” Flores and Margarito “Junior” Flores, identical twin brothers who grew up in Chicago’s Little Village but moved to Mexico, shipping tons of drugs back to Chicago, court records examined by the Sun-Times show.

The twins agreed to cooperate with U.S. investigators in late 2008, court records show, and Pedro Flores recorded a damning phone conversation with his supplier — El Chapo. The recording became the key evidence in the 2009 federal indictment filed in U.S. District Court in Chicago.

Guzman and dozens of underlings were charged with running a criminal enterprise that exported billions of dollars of cocaine and heroin to Chicago and other U.S. cities, according to the indictment.

In early 2016, El Chapo was extradited to New York, where he’s being held awaiting a trial set for September. The charges against him in the Chicago indictment have been rolled into the monumental case against him to be heard in Brooklyn. The case involves hundreds of thousands of documents and thousands of hours of secret recordings.

Chris Baines. | Arrest photo

FROM CHURCH USHER TO DEALER

In a series of emails and phone conversations from prison in Ohio, where he’s doing a 20-year sentence, Baines, 44, who was once a youth usher in church, talked about his middle-class background, his involvement with drugs and his unwitting role in the investigation of El Chapo.

His parents owned a grocery and liquor store near Columbus Park in Austin, and the family also lived in that West Side neighborhood. His late father also drove a Chicago Transit Authority bus, working the night shift. The family moved to Maywood when Christopher was 5.

In the late 1980s, Baines’ older brothers got shot to death within a year of each other, and Baines’ best friend also was killed. Baines was 14.

“It wasn’t the same when I lost my best friend and my two brothers,” he said.

Baines said he wasn’t a good student but managed to graduate from St. Joseph High School in Westchester, where he was a classmate of basketball players William Gates and Arthur Agee, who were featured in the acclaimed documentary “Hoop Dreams.”

He said he got a job at Riverside Mall in the suburbs and also worked for a couple of months at the Melrose Park post office. His parents tried to keep him away from the streets and the life that claimed his brothers, he said.

In 1991, he was gassing up his car in Maywood when a man came up and asked for an “eight ball,” street lingo for an eighth of an ounce of cocaine. Baines said he’d never dealt drugs before, but he agreed to do the deal for $150, then drove 10 minutes to the West Side and met with a drug dealer who’d been a friend of one of his brothers.

“He said, ‘No, I’m not going to get in trouble with your dad,’ ” Baines said. “But I said, ‘He’ll never know.’ He said, ‘OK, just bring me back $125.’ I met the guy in Maywood and made $25 in no time. Before you knew it, I was selling 10 eight balls a day. Then 100. And on and on.”

Still, Baines said he moved downstate to Bloomington, planning to attend a junior college, then go to Illinois State University, but that never happened. In 1992, he was arrested in Bloomington on charges of supervising 20 people selling crack cocaine. He was sentenced to 18 years in state prison for being the ringleader of a gang-related drug conspiracy that netted up to $10,000 a week. He was 19 years old.

In prison, Baines said he learned to be a barber. After he got out in 2002, he cut hair at Adams Barber Shop at Madison and Laramie on the West Side:

“I was making $1,000 a week when cuts were just $12 each. My parents were proud of me. I can cut all races and any style. I’m very fast and accurate.”

All of his pals were coming to see him at the popular barbershop, he said, “So it was only a matter of time before I got into the game.”

He supplied heroin and cocaine to lower-level dealers who sold drugs to gangs on the West Side. He said his middle-class upbringing set him apart.

“Most street guys that are in gangs are idiots, and they can only get so far,” he said. “I never got involved in gang activity, and I never hung with gangbangers.”

Baines said he lived with his parents during his year after he left prison in 2002, then he bought a house in Naperville but would stop by to see his parents, bringing them groceries and shoveling snow for them.

Meantime, he built up his network. Parker — the cousin involved in the July 3, 2007, buy that federal authorities arranged — and another cousin, Craig Smith, sold drugs for Baines, court records show. Smith, a heroin addict, tested the product, giving a thumbs-up when he thought customers would approve, the records show.

Even though Baines was arrested for selling small amounts of drugs to informants — 334 grams between July and December 2007 — authorities said he was a “mid-level” dealer. He agrees, admitting he bought from several major “connects” who supplied him with dozens of kilograms of cocaine and several kilos of heroin at a time.

Michael “Fat Mike” King — a bigger fish.

THE ‘FAT MIKE’ CONNECTION

One of his good friends was King, the trafficker known as “Fat Mike,” who weighed over 300 pounds and owned homes in upscale neighborhoods around Chicago — on the Gold Coast and in Country Club Hills, Willow Springs and Orland Park.

Court records show King’s homes were outfitted with concealed compartments in the walls where he’d hide drugs and cash. A 100-kilogram cocaine deal was no big deal for King, according to prosecutors, who said he got his drugs directly from the Flores twins in Mexico.

Baines and Fat Mike rode Harleys together and ate at places like Ruth’s Chris Steak House.

Baines said he didn’t want to do business with his good friend, so he went through an associate of King. But the relationship was rocky from the start.

Baines said the supplier, whom he would not identify, bought directly from the twins. “My first order was 25 ‘keys,’ ” he said. “I paid in three days. But he only gave me 12.”

Later, when a shipment of 35 kilos of cocaine and two kilos of heroin didn’t show up, Baines said he and his girlfriend flew to Cancun, Mexico, where the 6-foot-tall Baines met the 5-foot-4 Peter Flores in early 2007.

“He told us about a nice, newer hotel to stay at, so we stayed there along with his family,” Baines said. “He knocked on the door of my hotel room, and I went to answer it. He was so short! I looked down and said to him, ‘Damn, you’re a funny looking mother——.’ He was, like, ‘Man, f— you.’ We got alone fine after that.”

Baines said he learned that his Chicago supplier was cheating him, and he started dealing directly with Peter Flores. That didn’t last. Baines said he accepted a few multi-kilogram loads of drugs from the twins but stopped dealing with them in February 2007 because they were delivering low-quality cocaine and heroin, which were tough to move in Chicago.

“And I just didn’t trust them,” said Baines, who didn’t like that Peter Flores talked openly about his other customers.

According to court records, Baines also was buying heroin from Emeterio Gutierrez, whose family founded the popular but now-closed Mexican restaurant Nuevo Leon on 18th Street in Pilsen.

Gutierrez had worked in the restaurant and in his mother’s store before he started Bubbles Auto Spa in Cicero, where he met a cast of characters who introduced him to the drug business, according to court records.

“Emeterio Gutierrez was not my main connect,” Baines said.

Still, when authorities approached Gutierrez, he agreed to cooperate against Baines. Gutierrez and Baines’ courier, Christine Burgos, testified Baines was buying about a kilogram a week from Gutierrez in 2005 and 2006 and about two kilograms a month in 2007.

Baines incriminated himself, court records show, in hundreds of wiretapped calls in which he plotted drug deals and bragged he made $25,000 a month and drove a silver Corvette.

In July 2008, Baines and his network — Gutierrez, Burgos, Smith and Parker — were charged with drug conspiracy. All pleaded guilty.

Gutierrez got nine years in prison, Smith six years and Parker five years. Burgos got just a day in jail. U.S. District Judge Rebecca Pallmeyer hammered Baines with a 20-year prison sentence.

“There is no doubt in my mind that you were dealing in very substantial quantities of a drug that is dangerous and that destroys the fabric of our community and makes Chicago not a nice place to be,” Pallmeyer told Baines at his sentencing in 2014.

Baines said he “got screwed” for refusing to cooperate.

In his plea agreement, Baines admitted to four heroin deals that ranged from 29 to 165 grams, totaling 334 grams. Those were the sales to informants.

At his sentencing, though, prosecutors presented evidence Baines sold at least 30 kilograms of heroin, as well as cocaine.

“Anytime you don’t cooperate with the feds, they throw everything at you,” he said. “My case was a petty case. This is not fair.”

Shakeshaft, who prosecuted him, said: “If you cooperate, you have the potential to gain a benefit.”

Identical twins Pedro Flores (left) and Margarito Flores — the biggest drug dealers in Chicago history. | Arrest photos

WORKING UP THE CHAIN

Baines occupied one of the lower rungs in Chicago’s drug-supply chain. But information from wiretaps and informants in his case led investigators up the ladder, records show. “Fat Mike” King was a much bigger fish, and authorities quickly set their hooks in him, too.

Unfortunately for King, one of his biggest customers became a snitch for the DEA. The informant, who lived in Lexington, Kentucky, revealed that he and King had flown to the resort city of Puerto Vallarta, Mexico, in 2006 to meet with King’s suppliers — the Flores twins.

In 2008, the informant agreed to cooperate with investigators. He got King making incriminating statements on secretly recorded calls. In one, the informant spoke to King about a five-kilo cocaine deal.

The informant said he sent a courier to Chicago with $120,000 to pay King for the drugs, but he said police officers stopped his courier in a car outside Louisville, Kentucky, for doing 62 miles an hour in a 55-mph zone and took the money.

It was all a lie aimed at getting King to talk about the twins. But it got King worried because he was planning to pay Peter Flores with that money.

King called Flores, whom he referred to as “Slow Poke,” about what the informant told him. Then, he called the informant back. According to a transcript, King said of Peter Flores, “He ain’t mad.”

But King also warned the informant that Flores was worried someone in King’s organization was cooperating with investigators, not knowing it was the informant.

The transcript of another call, on June 22, 2008, reads like the goofy script of a Quentin Tarantino movie. King told the informant, “I’m going to buy me some mother—— patio furniture.”

“Patio furniture for your house?” the informant asked, incredulous.

“Hell yeah, man,” King responded. “Sit out there like them white people. Get me a TV out there . . .  It is roomy. I can get five, six people in there real comfortable.”

Soon, King’s suburban bliss would end. Presented with the evidence against him, he, too, agreed to cooperate, court records show.

King never went to prison. Suffering from diabetes and other medical problems, he died of natural causes before the case against him was resolved.

The informant, who admitted receiving up to 100 kilograms of cocaine a month from King between 1999 and 2008, pleaded guilty to drug conspiracy. He got 96 months in prison.

drug lord Joaquin "El Chapo" Guzman

Mexican drug kingpin Joaquín “El Chapo” Guzmán Loera — the prize catch at the end of the investigation. | AP

THE FINAL LINK TO EL CHAPO

Now, the Flores twins were in investigators’ sights.

The brothers — sons of a Mexican drug dealer who lived in Little Village — had become the most prolific drug suppliers in the city’s history, according to prosecutors. By the summer of 2003, they were moving two tons of cocaine a month from Mexico to Chicago, which became a major distribution hub — and moving more than $2 billion in cash to Mexico in less than three years, prosecutors said.

They’d been indicted in Milwaukee in 2005 on charges of selling more than five kilograms of cocaine. But no one knew the extent of the twins’ operation until the Chicago task force investigation that began in 2007.

El Chapo had met several times with the brothers and, in 2008, warned them to buy drugs only from him and stop doing business with the Beltrán-Leyva Organization, his enemies, according to court records.

On Nov. 6, 2008, they chose a third option. U.S. authorities — including Shakeshaft and DEA agents — secretly met with the brothers at a hotel in Monterrey, Mexico. They agreed to inform on El Chapo.

They ended up recording more than 70 phone conversations with Guzman. The most important call was on Nov. 15, 2008, when Peter Flores spoke with him. Flores was at his home in Guadalajara. El Chapo was in hiding somewhere in Mexico.

“Nice talking to you,” El Chapo said, according to the transcript of the call. “How is your brother?”

Flores bargained the price of 20 kilograms of heroin down from $55,000 a kilo to $50,000. “That price is fine,” El Chapo finally said.

With that, prosecutors had their first direct evidence of El Chapo negotiating a drug deal, said Shakeshaft, calling it “the case of a lifetime.”

In 2015, the Flores brothers — with their boyish looks and crewcuts looking more like Boy Scouts than drug dealers — were sentenced to 14 years in prison by U.S. District Judge Ruben Castillo, who warned them they’d always have to be looking over their shoulders for El Chapo’s assassins.

The judge said he was giving them a huge break because of their extraordinary cooperation against El Chapo.

The brothers are expected to be the star witnesses against him.

Though he’d been unaware of his role in the investigation that ended up landing the twins and El Chapo, Baines said it doesn’t surprise him.

“It’s a small world,” he said.