After a lifetime of service to his country, Jack Riley sat in his corner office overlooking the Pentagon planning a retirement playing golf.
As number two in America’s Drug Enforcement Administration, he had led the most successful operations in the agency’s history.
The target of his obsessions were either dead or safely put away.
But then in July 2015, Riley’s nemesis, Joaquin “El Chapo” Guzman, escaped.
While being held in Mexico’s supposed maximum security Altiplano prison, the leader of the murderous Sinaloa Cartel – the world’s biggest drug-trafficking organisation – fled through a mile-long tunnel built under his cell before riding away to freedom on a makeshift motorbike.
“I was going to retire until this d*** escaped,” Riley said.
Chapo had been his white whale, the object of an infatuation that sidelined everything else, including his family.
“I love my wife and kid, but I was never home for dinner,” said Riley.
What followed was a very personal four-year mission that this week ended with Chapo being put behind bars on US soil for life – and Riley finally retired.
After a three-month trial in New York, jurors found the Mexican guilty on all 10 charges after six days of deliberation.
They convicted the near legendary cartel boss of operating a continuing criminal enterprise, conspiracy to launder narcotics proceeds, international distribution of cocaine, heroin, marijuana and other drugs, and use of firearms.
He faces life in a “supermax” American jail in Florence, Colorado, known as the “Alcatraz of the Rockies” alongside Boston Marathon bomber Dzhokhar Tsarnaev, British shoe bomber Richard Reid and 9/11 conspirator Zacarias Moussaoui.
The verdict brought a welcome end to Riley’s decades-long hunt for America’s most wanted man, who once offered an £80,000 bounty to anyone who brought him the DEA agent’s decapitated head.
It is a fact Riley, 60, admits not only scared him but also “p***ed” him off.
In 2007, Riley was handed a transcript of a conversation wiretapped by his staff. It eavesdropped on Chapo’s men negotiating a price to kill him.
“I saw a transcript, and it basically said, ‘What do you think Chapo would give us to shut him up and cut his head off.’
“The joke is, they talked about only $100,000 (£80,000), which p***ed me off.
“What bothers me the most is I did exactly what that d*** wanted me to do. I got scared, and I started looking over my shoulder. And that’s what he intended.”
Riley is the son of a hospital pathologist and a nurse, and grew up in Chicago. His first jobs with the DEA had him working undercover as a 1980s yuppie making cocaine deals.
But he soon realised he wanted bigger fish – those who ran the operations.
As he worked his way up through the ranks, he became involved in combating the Colombia drug trade, helping bring down Pablo Escobar in Medellín and catch the leaders of the Cali cartel.
Then when during the early 1990s Chapo announced himself to the world by executing dozens of rivals and decapitating several Mexican cops, Riley’s interested piqued.
“The images were seared into my soul. I never forgot the brutality or the name,” Riley said.
Plus Chapo showed a gift for logistics no other cartel could match.
At one point, he was called “El Rapido” because of his ability to move drugs from Mexico into the States within 24 hours.
“Guzman was the most business-savvy son of a bitch who ever ran a criminal organisation,” Riley said.
His obsession with Chapo helped him become the head of the El Paso DEA office covering nearly one-third of the US-Mexico border.
Upon his arrival, Riley made known his sole intention was “to get El Chapo under control”.
His display of defiance did not go unnoticed. A sign reading, “Welcome Jack Reilly [sic]” was hung off a bridge just across the border in Mexico.
Weeks later as he drove along a deserted road, Chapo sent his men to give a warning.
Riley was pursued at speeds of up to 100mph before he got out of his car, gun drawn expecting a firefight.
But his pursuers inexplicably then sped off. Their job, however, was done.
“That whole thing was just to scare the s*** out of me,” Riley said.
However it only served to further cement his resolve.
“I got p***ed off and said, ‘It’s either him or me,’” said Riley.
“I’m a stubborn old Irish cop from Chicago. I’d put my money on me.”
Despite a move back to his hometown, Riley refused to let his hunt for Chapo die.
He began building a case in the Windy City targeting local gangs who worked for the cartel boss to stop the streets flooding with heroin.
Under one roof Riley brought together the DEA, FBI, state troopers and police to chase the “choke-point guys” – the brokers who were buying in bulk from Chapo before then selling it on to the gangs.
It opened huge resources to him including wiretapping local criminals’ phones. “What really stands out is how stupid all these guys were,” Riley said.
“On one call, [a dealer] is talking to Chapo’s guys in Mexico, and he says he thinks the ‘three letters’ [DEA] are onto us. So the guy says, ‘Don’t call me at this number anymore.’ Then he gives out his new number. We laughed our ass off in the office.”
Operation Strike Force was a huge success. Arrests and seizures rose, local drug lords fell and the busts netted millions in cash forfeitures.
In 2013, Chicago named Chapo Public Enemy No1 – and the fallout from Riley’s move surprised everyone, him included.
The Mexican government was bombarded with calls from enraged business leaders demanding the drug lord’s arrest.
“They screamed that Chapo was disgracing their country,” Riley said.
Authorities in Mexico immediately changed their approach, offering new levels of cooperation.
They pledged to hunt down Chapo in the hills and working hand in glove with the DEA they closed in on him.
US intelligence began monitoring the phones of those around him, so Chapo ordered his henchmen to dispose of their burner phones regularly, but many got lazy and didn’t.
The US also used drones to carry out surveillance of suspected hideouts, hoping to snap an image of Chapo.
The method led to several close calls – in one raid, Chapo escaped through a tunnel hidden beneath his bathtub – and ultimately his capture in 2014.
A year after Riley’s announcement, they chased him to Mazatlán and arrested him, without resistance, in his hotel room.
A few months after his capture, however, Chapo was gone through that mile-long tunnel from his Mexican prison cell.
Although only 5ft 5ins, the drug lord compensated for his short stature as a giant in the Mexican underworld.
He paid a reported £40million in costs and bribes to officials to remove more than 3,500 tonnes of earth to escape. It all added to the myth of El Chapo.
“One of the reasons he’s been successful is he’s used the media. There are folk songs written about him,” Riley said.
“There is the Robin Hood theory that he builds soccer fields and water purification. I’ve never seen any evidence of that, but he tries to paint himself that way. The only thing I know is he’s a stone-faced killer.”
Riley, by now second in command at the DEA, had flown down a few days earlier to notify Mexican officials that Chapo was planning to escape.
The alarm went ignored.
Then in late 2015, they got another break. Officials suspected Chapo was heading to Los Mochis, a coastal town in Sinaloa.
Surveillance images showed building crews reinforcing the front door on one house, and locals were overheard saying, “Papi is coming.”
In the end, “burritos and porn are what did him in,” Riley said.
It was January 2016, when Mexican officials saw a van leaving from a safe house late at night. Inside the vehicle, one of the men looked like Chapo.
“They were going out for burritos and porn – who else would need both at that hour?” said Riley.
After watching him return, the Mexican marines moved in. Chapo escaped through the sewer and emerged, carjacking a driver before finally being apprehended.
He was extradited to the US in 2017.
Riley, who is now retired, is happy his nemesis is facing life behind bars after
He has no love or admiration for Chapo. “He was 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. Explain it to me, ’cause I don’t get it. How did this f***ing mope become El Chapo?” Riley said.
But sadly such was his business acumen that the drug lord has left a deadly legacy.
Riley said: “All those routes he opened, all that fentanyl he shipped – he’s gonna kill our kids for years to come. This monster he built, it’s too big to fail now, thanks to him.”
‘Fling Penn in jail for cartel boss’s escape’
The cop credited with capturing Joaquin “El Chapo” Guzman says Hollywood star Sean Penn should be in prison for allowing the drug lord to escape arrest.
As Jack Riley, his DEA team and elite Mexican marines were poised to arrest the fugitive kingpin in October 2015 in a rugged mountain hideout in his birthplace of La Tuna, their mission had to be aborted when the Oscar-winning actor suddenly appeared.
Just as the order was about to be given to move in, Penn and Kate del Castillo, a Mexican soap opera actress who had praised Chapo online, bizarrely arrived at the compound.
The pair had arranged to met Chapo in secret for a film about his life before the Dead Man Walking star then published a gushing interview with the cartel boss in Rolling Stone magazine.
Fearing the civilians would be caught in the crossfire, commanders ordered the marines to stand down.
It gave Chapo the chance to escape.
Riley, who inspired Breaking Bad’s Hank Schrader, is furious Penn has not faced prosecution.
“Oh, my God. If I could get my hands on Sean Penn,” Riley said.
“The people he put at risk because of that stunt. He should be in jail.”
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