Joaquín “El Chapo” Guzmán — twice out of maximum security, finally extradited

On January 8, 2016, Mexican marines stormed a house in Los Mochis, Sinaloa, ending a six-month manhunt for Joaquín Archivaldo Guzmán Loera — “El Chapo,” the leader of the Sinaloa Cartel — who had escaped a maximum-security prison the previous July through a mile-long tunnel dug to the floor of his shower. He had escaped Mexican custody before, in 2001. He would not escape a third time. A year later he was extradited to the United States, and in 2019 a federal jury in Brooklyn convicted him on all counts.

Guzmán built and ran one of the most prolific drug-trafficking organizations in history, moving cocaine, heroin, methamphetamine, and marijuana into the United States across decades, and the violence that sustained that enterprise killed an uncounted number of people in Mexico and beyond. This file concerns the narrow arc the case ultimately turned on: his flight and capture. It treats the deaths around him — including the five cartel gunmen killed in the final raid — not as incident color but as the cost of an organization that defended itself with force.

The recapture was hastened by an unlikely vector. In October 2015, while Guzmán was a fugitive, the actor Sean Penn and the Mexican actress Kate del Castillo met him at a hilltop hideout for a Rolling Stone interview. Mexican officials later said the communications and movement around that meeting helped them close in. Marines tracked him to Los Mochis; in the raid five gunmen died and one marine was wounded. Guzmán slipped out through a storm drain and was caught hours later on a highway in a stolen vehicle.

He was extradited to the United States on January 19, 2017. His trial in the Eastern District of New York ran from November 2018 to February 12, 2019, when the jury convicted him on all ten counts. On July 17, 2019, U.S. District Judge Brian Cogan sentenced him to life in prison plus thirty years and ordered $12.6 billion in forfeiture. He is held at the federal supermax in Florence, Colorado.

Richard Matt & David Sweat — twenty days in the north woods, ended by gunfire

In the early morning of June 6, 2015, two convicted murderers were found missing from the maximum-security Clinton Correctional Facility in Dannemora, New York, the first escape from the prison’s secure perimeter in its long history. Richard Matt, forty-eight, and David Sweat, thirty-four, had spent weeks cutting through the steel wall at the back of their adjoining cells, working down through a labyrinth of catwalks and tunnels, sawing through a steam pipe, and surfacing through a manhole on a Dannemora street roughly a block beyond the wall. They left a taunting note behind. The breakout triggered one of the largest manhunts in New York history.

The escape was not a feat of solitary genius; it ran on inside help. A civilian tailor-shop instructor, Joyce Mitchell, supplied the hacksaw blades, drill bits, and chisels the men used, smuggling them past unmanned screening in frozen ground beef. A corrections officer, Gene Palmer, passed contraband for Matt’s paintings. Mitchell had agreed to be the getaway driver and to bring a gun; on the night of the escape she suffered what she described as a panic attack and never appeared, leaving Matt and Sweat on foot in the densely forested Adirondack borderland just south of Canada.

For three weeks the two evaded a force the State Inspector General later put at as many as 1,300 law-enforcement personnel, costing 22.8 million dollars in state overtime alone, who chased more than 2,500 leads through rain-soaked woods and abandoned hunting cabins. The arc ended in violence. On June 26, in the wilderness near Malone, U.S. Border Patrol agents confronted Matt after he fired a shotgun at a passing camper; he was shot and killed. Two days later, on June 28, a State Police sergeant spotted Sweat walking a back road near the Canadian line, gave chase across a hayfield, and shot him twice as he ran for a tree line. Sweat survived.

David Sweat, captured wounded and later recovered, pleaded guilty to first-degree escape and received an additional three-and-a-half to seven years on top of his existing sentence of life without parole. Richard Matt, who had been serving twenty-five years to life for a 1997 murder and dismemberment, died in the field. The escape exposed a culture of complacency at Clinton so thorough that, by the Inspector General’s account, basic counts and cell inspections that would have foiled the plot many times over had not been performed for years.