Rush hour starts early on Heroin Highway, generally by 6 a.m. Hockey dads in sport-utes; high school teens in car pools; commodities brokers and pensioners making their early-morning runs into Chicago on I-290. The Eisenhower Expressway – the Ike, as locals call it – is a straight shot in from the western suburbs to the mob-deep blocks of West Chicago. So Gangster Disciples and Vice Lords are up with the sun to pitch their work to the early birds, hugging the corners under the Ike's offramps to do much of their day's business by 8 a.m. Since cheap, potent heroin flooded Chicago 10 years ago and addicted a bell-cow demographic – middle-class whites – those corners off the Ike have become bull markets for gangs strong enough to hold them down. "They serve you in your car, quick-out in under a minute, and you're back home in Hinsdale before the kids wake," says Jack Riley, the ex-special agent in charge of the Chicago office of the Drug Enforcement Administration. "That's why gangsters kill for those corners. They're the Park Place and Boardwalk of the drug game."
Riley, the town's most famous federal agent since the days of the Untouchables, put together a strike force that jailed the major kingpins and left the gangs rudderless and scrambling. "We knocked down the big guys – the suppliers and OGs – but the young ones started killing their way up. That's what happens when you get your targets: The gangsters don't know who they work for." Actually, even before his strike force rolled up the leaders, no one here knew who they really worked for. Riley estimates that Mob City has 150,000 gangsters in residence – and though most are in endless wars with one another, they've all blindly served the same master for 10 years: Joaquín Guzmán Loera, better known as El Chapo. The king of all kings has likely never set foot here, though he made this city his American office, trucking heroin (and coke) from Mexico by the metric ton and taking billions of dollars out in small bills. Chicago has been a most congenial hub for Chapo. Centrally located and braided by interstates, it is a day's drive, or less, from most of America – and from the Mexican border.
For 15 years, Chapo has been Riley's white whale, the object of an obsession that teetered on derangement and sidelined everything else, including his family. "I love my wife and kid, but I was never home for dinner," says Riley, who fought Chapo's proxies in five different cities while rising through the chain of command at the DEA. Seven years ago, when he returned to Chicago for a third (and final) tour of duty, his charge was to quash Chapo's deadliest gambit: a species of heroin spiked with fentanyl that killed seasoned addicts by the hundreds. Riley stormed in, knocked a bunch of heads together and brought everyone – the DEA, FBI, state troopers and Chicago PD – under one roof to chase the "choke-point guys": brokers who were buying in bulk from Chapo and selling wholesale weight to the gangs.
By most measures, Operation Strike Force was a smash success; arrests and seizures soared, the local drug lords fell and the busts netted many millions in cash forfeitures, enough to pay the salaries of strike-force adjuncts. But by the only metric that mattered – the price of heroin on the street – Riley's mission was a wash. "It was 50K a kilo when we started this, and 50K a kilo" three years later, he says.
And so, in 2013, Riley summoned his stagecraft and pronounced Chapo public-enemy number one. At a press conference carried by hundreds of outlets, Riley and members of the Chicago Crime Commission proclaimed Chapo the greatest threat since Al Capone, a mass poisoner of the city and its suburbs. The fallout from Riley's broadside surprised everyone, Riley included. "At most, I hoped they'd find some corrupt colonel to go after him down there," says Riley. Instead, the Mexican government was barraged with phone calls from infuriated business leaders. "They screamed that Chapo was disgracing their country" and demanded his arrest, says Riley. Authorities in Mexico changed their tack, offering new levels of cooperation. That included a firm commitment to use SEMAR, Mexico's tactical corps, to hunt down Chapo in the hills. Working hand in glove, the DEA and SEMAR closed the net on Chapo. A year after Riley's announcement, they chased him to Mazatlán and arrested him, without resistance, in his hotel room. His escape from prison in 2015 merely prolonged the ending: He was busted by SEMAR (using DEA leads) five months after he'd fled. Thus fell the dragon: After a 30-year reign of murder and terror, Chapo was caught fleeing a sewer tunnel in a shit-stained tank top and chinos.
Last spring, I flew out to sit with Riley, who retired after Chapo's arrest. At 59, he'd moved with his long-suffering wife, Monica, to a resort town whose name I can't divulge. (For 10 years, Chapo has had a price on Riley's head, a threat confirmed in recent interviews with captured traffickers.) A ruddy, white-haired bruiser who holds court from a bar stool, Riley seemed dispatched from the days of fedoras and cops lighting Luckies at crime scenes. Born and raised in Chicago, he joined the DEA out of college and moved his family 12 times as he climbed the ladder. By the time he had quit last fall, he was the nation's number-two drug cop, having been at or near the center of nearly every major mission to catch foreign kingpins since the early Nineties. (It was his squad in Washington that built the intel platform to bring down Pablo Escobar in Medellín, Colombia; that helped catch the leaders of the Cali cartel and, later, the overlords in the Mexican mobs.) Riley recites their names, but they mean nothing to him now. Only Chapo endures, though he's being held at the Manhattan Correctional Center, where he awaits his trial of the century in New York.
"Part of me understands it – he's done, he'll die in jail," said Riley. "But the other part says, 'No, he's still out there.' All those routes he opened, all that fentanyl he shipped – he's gonna kill our kids for years to come. This monster he built, this Sinaloa thing: It's too big to fail now, thanks to him."
"Explain it to me," says one retired DEA agent. "How did this mope become El Chapo?"
In the months we talked, either in person or on the phone, Riley spoke of Chapo in the present tense, as though he were still at large at his mountain retreat, running the world's largest supplier of illicit drugs from a town without power or plumbing. Twice, Chapo had famously escaped maximum-security prisons, traveling Mexico in bulletproof cars to dine and frolic with call girls in seaside towns. Since 2001, when he launched a crusade to corner Mexico's $30-billion-a-year drug trade, he'd been everywhere and nowhere, growing the parameters of his empire and leaving defiled corpses as deed of ownership. He waged war by atrocity in Juárez and Tijuana, bribed generals and governors to feed him intelligence, and sent his lieutenants to the DEA, ratting on both his enemies and his allies. "Other bosses you waited out 'cause they always make mistakes," said Riley. "But this guy? Invisible. You couldn't find him."
He grunted and drained the last of his beer. We'd been at this bar for hours and hadn't looked at menus; Riley flagged the bartender and ordered lunch. Since retiring, he had spent his time knocking tee shots into tree lines and starting early on the day's first cold one. Maybe it was just his nervous system resetting, but six months after he left, he still mooned over Chapo, the enigma he never fully worked out: "He's on top for 30 years, has billions of dollars hidden – and he's a second-grade dropout who can barely read and write and has to dictate love letters in prison. So explain it to me, 'cause I don't get it: How did this fucking mope become El Chapo?"
If you wanted to create a nursery for narco princelings, you'd probably build your greenhouse in the mountains of Sinaloa, where the conditions for pathology are peak harvest. A dirt-poor ribbon of rivers and farmland on the southwest shank of Mexico's coastline, Sinaloa was largely ignored by the central government from the moment it became a state, in 1830. Roads went unpaved, villages did without schools, and no self-respecting official would visit the plazas of those remote, no-horse towns in the Sierra Madre. And so the peasants, left to their own devices, developed a shadow economy. In the 1920s and Thirties, they ran booze to Tijuana, where Hollywood's darlings blew in for the weekend to flee the dry torpor of Prohibition. Marijuana grew wild in the pastures; farmers trucked their bales five hours down the road to market in Badiraguato. In time, some harvested the poppy fields that Chinese tradesmen planted in the 1860s. Sons were taught by fathers how to bleed the bulbs for their vile-smelling opium gum. You couldn't make a killing, but you could make a sort of living if your kids didn't waste their days learning how to read.
That was Chapo's boyhood, and the boyhood, by degrees, of most of Mexico's drug lords of the past half-century. He grew up with, or close to, kids who became his partners and, eventually, his mortal foes: the Beltrán Leyva brothers, five cutthroat charmers who would one day be his enforcers and political fixers; the Arellano-Félix brothers, seven legendary sadists who roasted their victims alive in vacant fields. Even Chapo's mentors were from Sinaloa, first-gen capos like Don Neto and El Padrino, who turned a backwoods sideline into a multinational machine that stretched from Cancún to San Diego. To this day, Sinaloa's hills are to gangsters what western Pennsylvania is to frac pads and NFL quarterbacks.
"He came of age in the Eighties, when everyone got rich moving coke," explains one former Mexican operative.
Chapo was one of seven kids born to Emilio, a rancher, and Maria, a devout Catholic, in La Tuna, population 200. The family raised cows and grew sustenance crops behind a two-room house with dirt floors. What money they laid their hands on was earned uphill, where Emilio tended his poppies and marijuana. Once a month, he took the yield to Badiraguato. There he'd be paid for his contraband, then drink and whore all weekend and go home broke. A mean little man, he beat Chapo and his brothers; Chapo fled, for good, in his early teens. He stayed at his grandma's, grew his own weed and sent some of the proceeds home to feed his siblings.
Chapo (Spanish for "Shorty") was a small, squat teen who burned to spit his nickname in people's faces. He wore hats with tall crowns that lent him an inch or two, rocked on his tiptoes when talking to friends and later, as a boss, only posed for photos while standing on a custom-built stool. His will to power sprang from being the picked-on runt despised and driven off by his father. That's not junk science; it's the finding of the psychiatrist who assessed him as an adult in prison. While jailed for eight years in the 1990s, Chapo sat for therapy sessions. The psychiatrist filed a report on the man he treated. Chapo's "tenacity" and "disproportionate ambition" were wound to a sense of inferiority. To compensate, he craved "power, success and [beautiful women]," orienting his "behavior toward their obtention."
No farm was going to hold a kid like that, and at 15 or 16 (early details are murky) he won an introduction to the don of Badiraguato, Pedro Avilés Pérez. Avilés, the first of the air smugglers in Mexico, hired him to do odd jobs for his lieutenants. Chapo rode along on their runs to the U.S. border, soaking up knowledge of roads and checkpoints and befriending dispatchers and truckers. Though he couldn't read or write, he had a head for numbers and a steel-trap memory for detail. Best of all, he didn't have an ounce of mercy in him. Ordered to kill a man, he'd calmly walk up to him and put a bullet in his head.
Avilés' lieutenants were a dream team of smugglers. After Avilés was killed in a shootout with cops, they moved the operation to Guadalajara and named it the Federation. Chapo learned logistics from Amado Carrillo Fuentes, an avid flier who bought a fleet of planes and was nicknamed "Lord of the Skies." From Ismael Zambada, the silent assassin called El Mayo, Chapo learned to leverage violence just so, using only enough to send a message. And from Arturo Beltrán Leyva, he learned bribes were the grease that kept the wheels of power turning. "He was around smart guys and paid attention," says Alejandro Hope, a former senior operative with CISEN, Mexico's version of the CIA. "And his timing was perfect: He came of age in the Eighties, when everyone got rich moving coke."
Chapo's first big break was a quirk of history: the U.S. war on Colombia's cartels. In the 1970s, when Escobar and his counterparts in the Cali mob swamped Miami with coke, they put themselves in the crosshairs of the DEA. "They got rich, then they got lazy – they talked on their phones, which was how we finally took them down," says Riley. By the middle of the 1980s, U.S. Coast Guard cutters had sealed off the cartels' sea lanes in the Caribbean. The Colombians had no choice but to transship over land, sending their coke through Mexico to America. This arrangement wasn't new – they'd used Mexicans for years and paid them flat fees to serve as mules. But now all the leverage was with the Federation, and Chapo was the first to see it. "He said, 'Screw you, Pablo, I've got the smuggling routes. From now on, pay me in coke,' " says Carl Pike, a former special agent in the Special Operations Division, an elite unit created by the DEA that brings together the resources of a couple of dozen agencies to attack the cartels from all sides. "The Colombians took Chapo's terms because he was the best at what he did: getting their drugs off the plane and up to L.A. in 48 hours or less."
"Chapo was creating a new kind of cartel," says one expert.
Then a second piece of luck fell into Chapo's lap. El Padrino, his cartel leader, ordered the kidnapping and killing of a DEA agent named Kiki Camarena. It was a blunder that brought the hammer of God down: a tenacious offensive by the Mexican army, at the behest of the U.S. government. Padrino was arrested and sentenced to 40 years, handing off his kingdom to his capos. In 1989, Chapo's peer group divvied up the country: Amado Carrillo Fuentes took the routes through Juárez; the Arellano-Félixes got Tijuana and the coast, and Chapo took the run straight north to Arizona, sharing Sonora with El Mayo and the Beltrán Leyvas. He had recently turned 30 and was still wrapping his head around the burdens of excessive wealth. But he was already investing in creative fronts: "He bought a fleet of jets for 'executive travel,' and a grocery business to can cases of peppers that actually contained cocaine," says professor Bruce Bagley of the University of Miami, a cartel expert who's written six books on the narco-economy. "He was so sure of his supply lines that he guaranteed shipment. If any of his loads got seized by the cops, he paid the Colombians in full."
While the other capos got drunk on plunder, building villas with waterfalls and private zoos, Chapo lived like a handyman, sequestering himself on a dusty ranch 20 miles clear of Culiacán. (He was by then twice married, with at least seven kids; he'd go on to have 11 more by five women.) But it was his vision that firmly set him apart. "Chapo was creating the new cartel, a decentralized, hub-and-spoke model," says Bagley. "He saw what was happening to the top-down version: If you chopped the head of the snake off – Pablo being an example – the rest of his operation fell apart." Chapo formed alliances with local gangs and cut them in on his profits. He planted cells in new cities and left his staff alone to run them, and happily shared power with his closest partners, El Mayo and El Azul, a former cop. They were men like him: discreet and coolheaded, occupied only by business. The other lords' loud lifestyles were an affront to them. The only fit response was to take their routes from them – and Chapo knew whose turf to grab first.
The other capos got drunk on plunder – Chapo lived like a handyman on a dusty ranch.
There are roughly two kinds of agents who go to work at the DEA. The Type A's – Jack Riley, for one – are moral avengers who wage their war on drugs in a fissile rage. Then there's the second type: the behind-the-scenes mechanic who patiently builds a case for weeks or months, and goes home to his wife and kids at a decent hour.
Miguel Q. is a Type-B plugger who chased Chapo almost as long as Riley did. (Still on the job, he asked that I change his name; active agents risk their safety going public.) He's done multiple missions, on war-zone footing, in cities south of the border. He was on the scene for Chapo's arrest in 2014 – and his escape from prison a year later. "Most ridiculous engineering I ever saw," he says of the trench dug under Chapo's cell from a half-built house a mile away. "I mean, a dead-plumb line" from end to end, and "a hole just big enough for him to ride that cycle" and be out and on a plane back to the hills. "Who even thinks that, let alone does it?"
Well, Miguel, for one: He'd seen it up close as a young agent in the early Nineties. At the time, he was focused on truckloads of coke coming through major checkpoints out west. "It was Arellano-Félix dope, or so we thought," Miguel says – the cartel owned these particular checkpoints. Then his team started hearing chatter about a tunnel underneath the fence. A tip led them to a warehouse on the Mexican side, where miners were digging a quarter-mile tube, with rail cars, strong rooms and ventilation piping. It was a stroke of audacity and technical smarts far beyond the prowess of the Arellano-Félix Organization, who were brutal cocaine cowboys with a penchant for boiling rivals in acid and pouring their remains down a drain. "We're like, 'Who is this guy, and how many tunnels has he got?' " says Miguel. Hundreds more have been discovered in the decades since.
What vexed Miguel wasn't that he knew so little of Chapo; it was that no one in Mexico seemed to know him either. Since co-founding the Sinaloa cartel in 1989, Chapo had run it, yet there wasn't a single recent photo of him on file. It wasn't till his arrest, in June 1993, that the public got a glimpse of him. He'd been caught in Guatemala after fleeing the country in connection with a gunfight at an airport. The shootout had left several bystanders dead, including Juan Jesús Posadas, the cardinal of Guadalajara. Posadas' murder was an inflection point: the day that Mexico was forced to come to terms with the narco-state growing under its feet.
Chapo was convicted in a closed-door trial and given 20 years, hard time, for narco-trafficking. He treated this as a senseless inconvenience. At Puente Grande, a supermax facility 50 miles west of Guadalajara, he bought off everyone from wardens to washerwomen and settled down to do his business. He received his lieutenants in a sumptuous parlor and sent them away with detailed orders on where to ship his tonnage. He brainstormed markets with his older brothers, whom he'd deputized to manage his affairs. They were easy enough to reach; he had cellphones smuggled in. He was partial to BlackBerry, a Canadian company whose hardware was hellish to crack, says Pike.
But Chapo wasn't all work. He paid guards to round up hookers in town for orgies he threw in the mess hall. He kept up his spirits with fiestas and concerts: Chapo loved to dance with pretty chicas. The first feminist drug lord, he ordered the prison's integration with a select group of female convicts; one of them, Zulema Hernández, became his muse and in-house lover. He sent her schoolboy mash notes in hothouse prose that he dictated to his steno, a fellow convict. All the while, he juggled conjugal visits from his girlfriends, wife and ex-wife. The wear and tear of a multivalent love life took its toll on Chapo. Cocaine had previously been his drug of choice, but in jail he renounced it for Viagra. His people brought it in big batches, along with steak, lobster, booze and tacos – Chapo's weakness, besides women, was food. Eventually, the overindulgence levied its toll: At the time of his rearrest, in 2014, he'd been scheduled to meet with a specialist – "the penis-pump doctor to the stars," says Riley. "The vitamin V didn't cut it anymore."
"We knew he was moving tons while he was still in jail, " says one agent. "Turned out he had hired the warden"
In the end, though, he mostly used his time in jail to learn from the errors of other bosses. "Rule one: Don't talk on phones or send texts," says Miguel, who walks me through Chapo's communications methods. A densely complex system of encrypted squibs and Wi-Fi pings between lieutenants, it was built around a network of offshore servers that bounced the posts off mirrors in other countries. "We found 60 iPhones and hundreds of SIM cards when we raided his house in Guadalajara – and still we couldn't track where his calls came from," says Miguel. Chapo hired experts to constantly revise his tactics, and always made sure to toss his phones after a couple of days of use. He was an early adopter of social media, deploying hackers to mask his instructions to staffers on Snapchat and Insta-gram. "After years of trying to track him, we moved on in 2012 and got up on his tier-two guys – the bodyguards and cooks," says Miguel. Still, it took two years to divine his "pattern of life" – the small corps of people who served Chapo closely and could point to his general location.
Rule number two: Be a nimble supplier. He fitted tractor-trailers with elaborate traps – fake walls and subfloors that hid hundreds of kilos of product (and millions in shrink-wrapped cash on the trip back). He bought jumbo jets and filled them with "humanitarian" goods for drops in Latin America, then flew the planes back, bearing tons of cocaine, to bribed baggage handlers in Guadalajara. There were fishing vessels and go-fast boats and small submarines that could lurk underwater till the Coast Guard passed above. "We knew he was moving tons while he was still in jail, but we didn't find out how till later on," says Miguel. "Turned out he had literally hired the warden" to work as his logistics guy. That warden, Dámaso López, would vanish from sight shortly before Chapo escaped. Over the next 15 years, López rose through the cartel ranks, overseeing much of the daily churn while el jefe traveled the country dodging cops. Though Chapo trusted no one but family members and the men he came up with in Sinaloa, he made two exceptions to that rule. The first one was for López; the second, a pair of brothers who became his distributors in the States. In both cases, he'd have cause to deeply regret it.
Given his honeycomb of routes and the tonnage he pushed through, there wasn't much point in warring for turf. But something happened to Chapo during those eight years in prison, some fundamental shift in his sense of self. Once happy being the wizard behind the curtain, he now seemed intent on announcing to the world who the real boss had been all along. "He broke out of Puente Grande with an S on his chest, thinking, 'I'm the baddest motherfucker on the planet,' " says Dave Lorino, a retired DEA cop who helped mastermind the case against Chapo in Chicago. "He'd learned he could buy anyone, get out of any jail – and there was nothing that us gringos could do about it." "Prison made him hard, at least in his own mind, and all the other bosses were soft," says Riley. "He thought, 'Why should I settle for a chunk of the pie when I can have the whole thing?' "
After escaping Puente Grande in 2001, either crouched in a laundry cart or strolling out the door – "official" versions vary; none are confirmed – Chapo lost no time planting his flag. He paid Tejano pop bands to spread the news, crafting narcocorrida ditties that sang his praises and warned rival capos to leave town. Stories began running in the Mexican papers about Chapo's generosity to the poor. "He was building roads here and sewage plants there and schools in the pueblos and all that crap," says Riley. "But the hell of it is, we never found those schools – and if he ever built a road, it was for his trucks." The thesis of these ploys was always the same: Chapo was the great exception. He was the honorable capo who would swell peasants' hearts with his derring-do defiance of los Yanquis. "Please," says Riley. "This is a guy who chops heads off and leaves 'em in coolers."
In 2002, Chapo launched a war on the Gulf Cartel; he sent his death squad, Los Negros, into Nuevo Laredo to bang it out in the streets. The Gulf returned fire with its own band of crazies, a U.S.-trained group of army deserters who called themselves the Zetas. The Zetas were (and are) a special slice of hell, terrorists who happen to deal drugs for a living and are as happy killing citizens as narcos. To defeat them, Chapo upped his cruelty quotient. His assassins stormed a nightclub and rolled severed heads across the dance floor. Body parts were stuffed in the mouths of dead Zetas as dumb-show warnings to his foes: "A hand in the mouth meant you'd stolen from him; a foot meant you'd jumped to the other team," says Riley.
By 2006, Chapo's violence was general in Mexico. He pushed his fight with the Zetas into Juárez, where the gutters ran red for years. Tens of thousands of people were slaughtered in Murder City, as Juárez came to be known. Riley was the agent in charge of El Paso, Texas, when the worst of the carnage erupted. "We'd intercept calls from the other side of the fence" – Chapo's hit squads checking in with their bosses. "They'd say, 'We took care of that thing on Calle so-and-so; what else you got for us tonight?' "
Being two miles from bedlam – with no jurisdiction – drove Riley to desperate measures. He broke with protocol and phoned the local papers, calling Chapo a "coward" and a "butcher." Chapo took the bait: He put a hit out on Riley. One night, Riley was at a gas station refueling when two men in a pickup pulled in. They got out of the truck and came at him in the dark. He drew his pistol first. They turned and fled. "Maybe that was a warning: 'Back off and shut up,' " he says. "I hope he knew better than to have me whacked. He'd seen what happens when you shoot DEA."
History bears this out: Chapo has never killed a fed or declared war on the U.S. government. But it's clear now that he entertained the option. According to multiple witnesses who'll testify at trial, Chapo went looking for heavy ordnance in 2008 to attack the U.S. Embassy in Mexico City. He was furious at extraditions of cartel leaders, who were getting long sentences in U.S. courts and dispatched to spend their days in federal pens. Many of them were sent to Supermax, a facility in Colorado where inmates live in near-total isolation. It was one thing to do time at Puente Grande, where a man of Chapo's means could live like a pimp while waiting for his crew to dig him out. It was another to go to Supermax, where anyone wishing to pay him a call would be subject to extreme vetting by U.S. Marshals.
In 2007, Chapo tipped the DEA off to a coke shipment coming from a man he'd grown up with. "Chapo was basically saying, 'No more friends,' " says one agent.
Still, that Chapo would consider buying a bomb suggests that he'd lost his bearings. In 2007, Miguel was stationed in Guadalajara when he got a hot tip from Chapo's camp. A ship from Colombia was bound for Manzanillo with an enormous cache of coke onboard. Of even greater interest was the name of the cocaine's owner: Arturo Beltrán Leyva, or ABL. Chapo and ABL had been like brothers since their teens in Badiraguato. They'd made each other rich with their complementary gifts: Chapo the genius at blazing new routes – ABL the master of pervasive bribes. To be sure, there'd been tensions building between them – but what made Sinaloa the world's biggest drug gang was its settling of internal disputes. Its bosses had stuck together while Chapo was away, then welcomed him back, without a squawk, when he returned to his seat of power in 2001.
"For Chapo to reach out about ABL's dope – yeah, I was shocked," says Miguel. "All those years together and all the money they made? Chapo was basically saying, 'No more friends.' " One morning in the fall of 2007, Miguel and 120 heavily armed troops descended on the freighter. Unsealing the shipping pods, they found double what was promised, almost 25 tons of cocaine. Gathered end to end, it ran four basketball courts in length. Street value: $2 billion. "When we loaded it out to burn on the Army base, it was the biggest fire you ever saw," says Miguel. "And I had to stick around for every minute, make sure no kilos went out the door." With the exception of El Mayo, Chapo had burned all his bridges; he was now, like Macbeth, so steeped in blood that there was no going back, only forward.
Somewhere in America, in the witness-security wing of an undisclosed federal prison, sit the two men whose testimony will seal Chapo's fate. Margarito and Pedro Flores, identical twins in their thirties, are two of the least fearsome thugs on the planet, nerds who somehow noodled their way to the center of Chapo's circle. "They're, like, five-foot-five and a buck-40," says Lorino, who spent months debriefing them when they surrendered, in 2008. "I laugh when I read that they're Latin Kings. Real Kings would eat 'em for lunch and still be hungry."
In 2005, while launching his quest to monopolize Mexico's drug trade, Chapo was told about a pair of Chicago natives with the best broker network in the country. For years, the Flores brothers had been buying in bulk from one of Chapo's lieutenants near the border. They were smart and street-avoidant, faithfully paid on time and looked like they worked at a Wendy's in La Villita, the barrio on Chicago's West Side. Chapo was intrigued. Set a meeting, he told his guy. The twins were brought to Mexico for the rarest of honors: a face-to-face with Chapo at his compound.
Chapo was impressed when he sat with them: They were all about business, not bravado. He and his principal partners, El Mayo and ABL, came to an agreement on a deal. They would front as much dope as the twins could handle and give them a break on the price. They would also allow them to buy on terms instead of cash on delivery for each load. For the twins, it was like cashing a Powerball ticket. In the summer of 2005, they swamped Chicago with Chapo's H. Almost immediately, the city's hospitals were packed with ODs: Newbies and junkies abruptly stopped breathing after snorting or spiking the product. The Chicago DEA went to wartime footing, scrambling to interdict the lethal batch that would kill a thousand people in less than a year. Agents traced the dope to a lab near Mexico City. "Chapo had brought in chemists to make it extra-super-duper," says Riley. How? By adding fentanyl, a synthetic narcotic that looks (and cooks) like heroin. "It's 30 to 50 times stronger than heroin, and you can't tell which from which when you cut 'em up." In May 2006, authorities raided the lab and arrested five employees. One of them had been busted in California for manufacturing fentanyl.
But Chapo shrugged off the takedown. He had a vise grip on Chicago – and Milwaukee, Detroit, Cincinnati, Columbus, Ohio, and cities farther east that the twins supplied. From 2005 to 2008, they moved $2 billion of Sinaloa's product. The arrangement worked smashingly for the cartel. It was supplying half the coke and heroin in America, according to reports by the Justice Department. It had partners in West Coast cities, was moving heavily into Europe and planting new cells in South America. With cash pouring in from every port, it was paying hundreds of millions a year in bribes to Mexican officials, and getting white-glove service in return. Attempts by the DEA to catch Chapo and his partners were subverted time and again by intel leaks. "Outside of SEMAR, there was no one we could trust," says a frustrated DEA hand. "We'd feed them information and our informant would turn up dead." Often, Chapo would saunter away minutes before a raid, as if to thumb his nose at the pinche gringos.
He'd become, in short, the man he dreamed up as a pudgy teen in La Tuna. No one could touch him, and everyone feared him. He even had the requisite beauty-queen wife: In the summer of 2007, he married Emma Coronel, Miss Coffee and Guava. Their wedding was virtually an affair of state. Drug lords and ladies flocked to the event, dancing to Tejano combos playing songs of praise for the groom. For added amusement, the Mexican army swooped down to finally corner Chapo. This time, he didn't even make it exciting. He skipped out a full day early, having fed the generals a phony wedding date.
In May 2008, Chapo called the Flores twins to a summit at his compound in La Tuna. Pedro couldn't make it, but Margarito went, taking the five-hour car ride up the mountain. He'd done this once before, but something was different this time: As he glanced out the window, he saw bodies chained to trees, their flesh being eaten by coyotes. He'd been in the game long enough to know what that meant – there was a tree along that road reserved for him.
At the meeting in La Tuna, Flores was given an ultimatum: Stop buying ABL's dope now, or else. "Chapo told him to pick a team – and he only warned people once," says Lorino, the retired DEA agent. "He liked the twins personally – they'd made him a lot of money," but he was prepared to kill them and forfeit billions to settle his accounts with the Beltrán Leyvas. This put the Flores twins in a desperate fix: Soon after, ABL called and told them not to buy from Chapo. Caught between two killers, the twins weighed out the options, then phoned their lawyer in Chicago. Reach out to the DEA, they told him – "We'll give them Chapo and ABL if they protect us."
In June 2008, DEA agents flew to Mexico to sit with the Flores twins. "We needed a lot of convincing; we'd been promised Chapo before," says Lorino, who was at the meeting. "But the twins, man, they had the bona fides." There were stacks and stacks of logbooks listing every drug shipment, four dozen cellphones with texts and voicemails saved from Chapo's lieutenants, and flowcharts of brokers back in the States who were buying hundreds of kilos apiece. It was one of the greatest caches of court-admissible evidence in the history of the War on Drugs, but the DEA wanted more: It wanted Chapo himself on tape. In exchange for reduced sentences in a witness-protection wing, the twins agreed to stay in Mexico for several months and record their every phone call with the cartel. They also promised to tip the DEA to each major shipment going north. Lorino returned to Chicago and assembled a team of agents to obtain warrants, tap phones and stage raids. Then he sat and waited, holding his breath.
"In two weeks, we got the first call," says Lorino: a quarter-ton of coke in a produce truck. He alerted state troopers, who pulled over the semi a half-hour south of Chicago. Major takedowns followed for the next four months. Stash houses, count houses, tractor-trailer loads – three tons of cocaine and heroin were seized, $22 million in cash was recovered, and 68 people were arrested in Chicago, many of them brokers and gang chiefs. By November, the feds had their sweepstakes ticket: two crystal-clear audio recordings of Chapo and Pedro Flores discussing a 20-kilo order of heroin on the telephone. "I was putting my daughter to bed when my cellphone rang: 'Dave, we got the big guy on tape,' " says Lorino. "I said, 'Dude, if you're fucking with me, I'll end your career.' But he said, 'Nope, it's over. We got him cold.' "
In the following years, Mexican soldiers and marines killed or caught dozens of the 37 tier-one drug lords on the country's kingpin list. Chapo was the 33rd to be nailed. He was first busted in February 2014 in Mazatlán. But the following summer, he was gone again, vanishing down the wormhole below his cell. Riley, who'd left Chicago for Washington, D.C., to take the number-two job at the DEA, let himself seethe for 10 minutes. Then he made calls to Mexican officials, demanding they dedicate a SEMAR unit to a third, and final, arrest. SEMAR is the unicorn of Mexican law enforcement: a bribe-proof corps of tactical fighters trained by U.S. soldiers in Colorado. Small in relative numbers (there are just 16,000 marines), they rarely stay in one place long, racing from fire to fire. But the government, mortified by Chapo's escape, agreed to Riley's terms. It dispatched 100 marines to track down Chapo, using leads from the special-ops group in D.C.
"We went back to what we knew – get up on his people," says Riley, meaning the cooks and drivers who serve him. Pings from their phones suggested Chapo was in the hills, moving nightly between a cluster of farms in and around La Tuna. SEMAR rallied for an all-out raid, then got orders from the top to stand down. "I was furious," says Riley. "What's the fuck-up this time?" He learned after the fact that the actor Sean Penn, on assignment from Rolling Stone, had gone up the mountain to see Chapo. SEMAR was instructed to wait till Penn and his associates left, then go in hot and heavy. This it certainly did, storming La Tuna in a shoot-'em-up, weeklong siege. Eight people perished, none of them Chapo. Reportedly, a SEMAR marksman had him in his sights as he ran from one of his ranches. But Chapo was carrying a small child, and the marine declined to fire. Chapo slipped into the bush and disappeared.
When Chapo was caught, one agent couldn't believe it. "I wanted pictures of that prick in cuffs," he says.
For weeks, he and his henchmen went zero-dark silent: No calls or BlackBerry messages hit the wire. Then someone saw Ivan, Chapo's son and security chief, scouting neighborhoods in salty Los Mochis. A sweatbox of a city on the Sinaloan coast, it had everything Chapo lacked while he hid out in the hills: fiery taquerias, underage hookers and an easy in-and-out by land and sea. SEMAR sent spies in civilian clothes to check out the report. They fixed on a bloc of condos getting aggressive renovations – loads of steel and concrete were arriving daily. For weeks, the spies lunched at a corner bodega and heard chatter among the workmen that "Grandpa" was coming. Late one January night, sitting vigil across the street, they saw a white van leave the complex. There were three men inside it; one of them looked like Chapo. "They were going out for burritos and porn – who else would need both at that hour?" says Riley.
Before dawn on the morning of January 8th, marines stormed the condo. Inside was a maze of reinforced doors designed to blunt and confuse them. By the time they crashed the right one and killed Chapo's gunmen, he'd bolted down an escape hatch under a closet. Accompanied by El Condor, his lieutenant and chief assassin, he slogged through thigh-deep water in the sewers. Emerging a mile later, he was barefoot and filthy; none of his men were there to scoop him up. Chapo jacked a car, ordered its occupants out at gunpoint, then raced through town, heading south. He made it a couple of miles before police cut him off; the prolific killer went meekly. For the third and last time, he'd surrendered without a shot after his men fought and died to protect him.
Riley was at a ceremony in Quantico, Virginia, presenting badges to a class of new agents. His cellphone, on vibrate, kept growling in his pocket; it all but killed him not to answer for an hour. When at last he ducked out, he got the word from his team: Chapo was being held by the cops. "I refused to believe it till they sent me proof. I wanted pictures of that prick in cuffs." An hour or so later, a photo came through: Chapo sitting disheveled, in a dirty wife-beater, his hands bound tightly behind him.
Riley informed his chief, thanked his counterparts at SEMAR, then rounded up the boys to celebrate. They all piled out to a bar in Crystal City – a dozen senior DEA agents roared like pledges at the final keg party of rush week. News of Chapo's capture flashed across the television. From then on, none of them could pay for drinks; fellow patrons bought toast after toast. "We were badly overserved," Riley recalls, still basking in the glow of that night. Alas, he was so excited that he did it again the next day, and the day after, and the day after that. Finally, his wife said enough. "Chapo never managed to kill you," she said. "But keep this up and you sure will."
A year and a half later, Chapo sits in his cell, quietly losing his mind in solitary. He is denied human contact, except with his lawyers; his wife and kids are barred from seeing him. One hour each weekday, he leaves his cage for a slightly bigger enclosure. There, he can either ride an exercise bike or watch a nature program; the TV isn't viewable from the bike. His hair is falling out and his "mental health" declining: He suffers "auditory hallucinations," per his lawyers. "We run a real risk of him going crazy," says Michael Schneider, a senior public defender on Chapo's team.
Chapo faces 17 counts in Brooklyn's federal district, including charges of narco-trafficking. A conviction for narco-trafficking would get him life without parole under federal kingpin sanctions. In no known universe does he stand to beat those charges. Among dozens of witnesses on the government's list are fellow narcos who've pleaded out for shorter terms. The most crucial, of course, are the Flores twins, whose encyclopedic records are damning to the point of overkill. "His lawyers can attack them till the cows come home – there's nothing they can do about those tapes," says a U.S. attorney. Adds Riley, with a sprig of Gaelic glee, "How great that the rap he can't get out of is for 20 lousy keys of smack. He wipes out Chicago and kills tens of thousands of people – and his smallest deal is the one that does him in."
Then there are the indictments in five other cities, though no one thinks those trials will happen. The likeliest outcome, say those close to the case, is that Chapo pleads guilty to an omnibus proffer that settles all counts, Brooklyn's included. Says the U.S. attorney, "He can't win at trial, but he has assets he could trade" for better conditions in prison. It's presumed that Chapo's hiding billions of dollars in cash and business holdings. If the feds want that money, they will need his help to find and claw it back. A second bargaining chip is his years-long log of bribes paid to Mexican officials. Under the Obama administration, that log would be worthless – but in the age of Trump, it's priceless. Vicente Fox, the ex-president who compared Trump to Hitler, has long been accused of taking money from Chapo in exchange for going easy on Sinaloa. President Enrique Peña-Nieto, who vowed never to fund Trump's wall, lost close colleagues to bribery charges after Chapo fled in 2015. If Chapo has any proof that he paid those people, he'll be holding a set of aces when the dealing starts.
Finally, there's the question of his legacy. For years, experts thought that the syndicate he built would stand long after he fell. "If you kill the CEO of General Motors, General Motors will not go out of business," said a Mexican official to The New Yorker. But 20 months after Chapo's final arrest, his monolith is falling apart. His sons – the "Chapitos" – are at war with Dámaso López, the ex-prison warden who helped Chapo flee and became his key lieutenant for 15 years. In February, López lured the sons to a narco summit in Sinaloa. Gunmen broke in and tried to kill the Chapitos, who fled, on foot, into the brush. "This was weeks after Chapo was extradited – the war to replace him was on," says Alejandro Hope, the ex-intelligence officer for the Mexican CIA. It was a bold betrayal and a sign of the chaos to come.
Ten years ago, five cartels ran Mexico. Now there are 80 splinter sets, all of them vicious and unstable. Beheadings are banal, civilians are being slaughtered and the government hasn't the faintest clue how to stem the havoc. Mad as it sounds, we may mourn the passing of Chapo. He was the Assad of cartel bosses, but he kept the carnage bottled, stopping at his side of the fence. What replaces him – chaos – respects no borders. We could wake one day and find we're next door to Aleppo, with flames overleaping our beautiful wall.
Watch our exclusive interview with El Chapo from 2016.