He was a ghost that refused to stay in the shadows. Most people know him as "Popeye," the right-hand man to Pablo Escobar, but the reality of John Jairo Velásquez Vásquez is way more complicated than a Netflix series or a viral YouTube video could ever portray. He didn't just witness the rise and fall of the Medellín Cartel. He was the trigger finger.
You’ve probably seen the interviews. The chillingly calm demeanor. The way he spoke about murder as if he were describing a mundane trip to the grocery store. It’s haunting. Honestly, there’s a weird fascination with him because he’s one of the few high-level "sicarios" who didn't end up in a shallow grave or a permanent DEA cell in the States—at least, not initially. He survived. Then he talked.
The Making of Pablo’s Most Famous Hitman
John Jairo Velásquez Vásquez wasn't born a monster. He actually spent time in the Colombian Navy—where he allegedly earned the nickname "Popeye" because of his distinct physical profile—and even briefly attended police school. Imagine that. The man who would eventually help dismantle the Colombian state started by trying to join it.
Life took a sharp turn when he met Escobar. To Popeye, Pablo wasn't just a boss. He was a deity. This wasn't business; it was a cult of personality. He once famously said that if Escobar told him to kill his own father, he would have done it without blinking. That level of devotion is hard to wrap your head around, but it explains how a single individual could claim responsibility for over 300 personal kills and the coordination of thousands more.
He wasn't just a guy with a gun. He was a manager of death. While other sicarios were just muscle, Popeye was operational. He handled the logistics of some of the cartel's most high-profile atrocities. We’re talking about the Avianca Flight 203 bombing and the kidnapping of presidential candidate Andrés Pastrana.
The Crimes That Defined an Era
When you look at the track record of John Jairo Velásquez Vásquez, the numbers lose their meaning. Three hundred? Three thousand? It becomes a blur. But specific events stick out because they changed the course of Colombian history.
Take the 1989 bombing of Avianca Flight 203. The goal was to kill César Gaviria, then a presidential candidate. Gaviria wasn't even on the plane. 107 innocent people died. Popeye later detailed how they tricked a young man into carrying the briefcase bomb, telling him it was a recording device to spy on an official. The kid blew up along with everyone else. It’s gut-wrenching.
Then there was the assassination of Luis Carlos Galán. Galán was the hope of a nation, a man running on a platform of extradition and cleaning up the narco-influence. Popeye and his team snuffed that hope out in a public square in Soacha. These weren't just "hits." They were messages designed to bring a government to its knees.
One of the most bizarre and tragic stories involves his own girlfriend, Wendy Chavarriaga Gil. She had been Escobar’s lover first. When she became a mole for the government, Escobar gave the order. Popeye didn't hesitate. He set up the meeting and had his men do the job, or as some reports suggest, he was right there for the final moment. He spoke about this later with a disturbing lack of regret, citing "loyalty to the boss" above all else.
Prison, Parole, and the YouTube Pivot
In 1992, as the Medellín Cartel was collapsing, Popeye surrendered. He spent 22 years in prison. Most people thought that was the end of the story.
It wasn't.
He walked out of Cómbita prison in 2014 and did something nobody expected: he became a social media star. He launched a YouTube channel called "Popeye Arrepentido" (Repentant Popeye). It was surreal. You had a mass murderer with over a million subscribers, filming videos where he’d walk through the streets of Medellín, point at a corner, and say, "That's where we killed those three cops."
Critics were rightfully disgusted. They argued he was "narcotraficante-chic," glamorizing a dark past while the victims' families were still mourning. He claimed he was warning the youth against the life of crime, but he often looked like a man relishing his former glory. He’d sign autographs. People took selfies with him. It felt like Colombia was suffering from a collective Stockholm Syndrome.
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But he couldn't stay out of trouble. The "repentant" part of his persona seemed to be a thin veil. In 2018, he was arrested again. This time, it wasn't for 80s-era terrorism; it was for extortion. He was allegedly linked to a "re-collection" scheme involving assets from the old days.
The End of the Line: Cancer and a Quiet Death
The bravado finally hit a wall in early 2020. John Jairo Velásquez Vásquez died of stomach cancer at the age of 57. He passed away in a hospital in Bogotá, a far cry from the violent, bullet-riddled end most of his contemporaries met.
His death sparked a weird mix of reactions. Some felt cheated that he didn't serve more time or face more direct justice for the thousands of lives he ruined. Others felt his death marked the final closing of the book on the Escobar era.
What’s left? A legacy of blood and a lot of questions about how society consumes "true crime." Popeye was a master of his own narrative. He knew that if he kept talking, people would keep listening. He turned his atrocities into a brand.
What This Story Actually Teaches Us
If you’re looking at the life of John Jairo Velásquez Vásquez, don't just look at the body count. Look at the mechanics of the "sicariato." It's a reminder of how easily a society can be destabilized when the line between the law and the underworld blurs.
Here are a few takeaways that actually matter if you want to understand the modern context of Colombia:
- The Power of Narrative: Popeye proved that if you control the microphone, you can reinvent yourself. His YouTube career is a case study in how "bad guys" use digital platforms to bypass traditional media scrutiny.
- The Fragility of Peace: His re-arrest in 2018 showed that the "old guard" of the cartels often leaves a lingering shadow. Transitioning from a war-torn narco-state to a peaceful democracy is a process that takes generations, not just a few peace treaties or prison sentences.
- Victim Erasure: In the frenzy of "Narcos" and "El Patrón del Mal," the victims of men like Popeye often get relegated to the background.
If you want to dig deeper into this, don't just watch the glamorized shows. Look into the archives of El Espectador, the newspaper that stood up to Escobar even after their building was bombed and their director was murdered. Read the testimonies of the families of the Avianca flight. That’s where the real story of Colombia lies—not in the self-serving tales of a man who killed for a living.
To truly understand the impact of this era, the next logical step is to research the "Extraditables" and how the legal battle over extradition shaped Colombian sovereignty in the 1980s. Understanding that legal struggle explains why men like Popeye were so desperate to fight the state in the first place.