Escobar Hitman Popeye Coordinated 3,000 Cartel Killings Before Launching Unprecedented YouTube Channel

BOGOTÁ — He orchestrated the murders of 3,000 people, survived 23 years inside maximum-security prisons, and walked out to command a digital audience of millions.

Jhon Jairo Velásquez was Pablo Escobar’s premier executioner.

Operating under the underworld moniker “Popeye,” Velásquez personally pulled the trigger on more than 250 victims during the bloody zenith of the Medellín Cartel. He hunted down Cabinet ministers, rival drug lords, investigative reporters, and police officers. He bombed a civilian airliner mid-flight, killing 110 people to eliminate a presidential candidate who was not even on board. Yet after serving nearly a quarter-century behind bars for terrorism, murder, and narcotics trafficking, Velásquez engineered a second act that stunned Colombian society: he became a digital media celebrity.

Through his YouTube channel, titled “Repentant Popeye,” Velásquez weaponized his lethal notoriety, firing scathing polemics at the Colombian political establishment while coolly dissecting the mechanics of his historic atrocities.

The Making of Escobar’s Lead Enforcer

Born in Yarumal in 1962, Velásquez abandoned high school to enlist in the Colombian Navy, where peers coined the nickname “Popeye” in reference to his physical appearance. He departed the military to enter police training, but the academy quickly dissolved into another dead end. At 17, a friend landed him work as a driver and bodyguard for a young woman who was dating Pablo Escobar.

The Medellín Cartel noticed his cold detachment.

By 18, Velásquez received his first execution order. Escobar wanted a municipal bus dispatcher dead after the man pulled away abruptly at a transit stop, throwing an elderly woman—the mother of Escobar’s close associate—to the asphalt and killing her.

With that single hit, Velásquez earned Escobar's absolute trust. He rose rapidly to command squads of cartel gunmen throughout the 1980s, enforcing Medellín’s territorial dominance through unsparing violence. That loyalty extended to his own personal life. Around 1984, Escobar ordered the assassination of Wendy Chavarriaga Gil—Escobar’s former partner, whom Velásquez had fallen in love with—suspecting she was passing intelligence to state authorities.

Velásquez did not hesitate. He lured her into an ambush executed by his subordinate hitmen, later stating he could not bear to pull the trigger himself.

Bloodbath Across Colombia and the Avianca Flight 203 Bombing

By 1988, the Medellín Cartel was waging open war against the Colombian state to smash extradition treaties with the United States. Velásquez stood at the operational center of every major strike.

In January 1988, he orchestrated the abduction of Andrés Pastrana Arango, then campaigning for mayor of Bogotá. National police units rescued Pastrana a week later—and he went on to win the presidency of Colombia a decade later in 1998. Just seven days after snatching Pastrana, the cartel kidnapped Attorney General Carlos Mauro Hoyos. When army battalions encircled the region, Velásquez disguised himself in a sweater and thick spectacles, bluffing his way through military barricades by claiming to deliver urgent medicine to an ailing relative. He reached the safehouse ranch and pumped three rounds into Hoyos.

In August 1989, Velásquez coordinated the assassination of Liberal Party presidential frontrunner Luis Carlos Galán. Hitmen gunned Galán down in Soacha in front of 10,000 supporters, breaching an 18-man security ring as the politician stepped onto the campaign stage.

Three months later came his most catastrophic operation.

On November 27, 1989, Avianca Flight 203 departed Bogotá bound for Cali carrying 101 passengers and six crew members. Velásquez and cartel operatives had duped an unwitting young man into carrying an explosive briefcase onto the Boeing 727, instructing him to press a button to activate what he thought was an audio recording device. The bomb detonated at cruising altitude over Soacha. All 107 people aboard perished, alongside three residents struck by raining fuselage on the ground. Escobar aimed to assassinate presidential contender César Gaviria, who had cancelled his seat at the final hour. Gaviria swept the 1990 presidential election.

From La Catedral Fortress to Digital Video Confessions

When Escobar brokered a conditional surrender with the Colombian government in 1991 to avoid extradition, Velásquez entered La Catedral—the custom luxury prison Escobar constructed for himself in Envigado—to serve as the boss's personal security chief. When Escobar escaped in July 1992 amid a state push to transfer him, Velásquez fled alongside him.

His flight did not last long. In October 1992, with security forces tightening their dragnet and the Medellín Cartel disintegrating under rival assaults, Velásquez surrendered to federal prosecutors.

Colombian courts convicted him of murder, narco-terrorism, criminal conspiracy, and extortion, handing down the statutory maximum sentence of 30 years. Velásquez served nearly 23 years across several penal facilities before winning conditional release in 2014.

Velásquez remained under scrutiny by state prosecutors for extortion and criminal ties until his death from stomach cancer in February 2020 at age 57, closing the chapter on one of South America's most lethal criminal lives.