If you’ve seen the 2006 documentary Cocaine Cowboys, you probably think you know Jon Roberts. He was the charismatic, smooth-talking New Yorker with the silver hair who practically built the Medellín Cartel’s distribution network in Miami. But honestly? The movie barely scratched the surface. It was the "PG" version. The real story—the one buried in the 500-plus pages of American Desperado—is way darker, weirder, and more disturbing than a ninety-minute documentary could ever handle.
I’m talking about a guy who didn't just sell drugs. He lived a life that sounds like a fever dream written by a nihilistic screenwriter. Born into Mafia royalty, trained as an assassin in Vietnam, and eventually becoming the secret weapon of the Colombian cartels.
Jon Roberts wasn't just a criminal. He was a force of nature.
The Mafia Kid Who Saw Too Much
Most kids are playing with blocks at age seven. Jon Roberts (born John Riccobono) was watching his father, a Gambino family associate, execute a man on a bridge. That’s not a metaphor. His dad literally took him along for the ride, popped a guy in the head, and then they went about their day.
Talk about a skewed moral compass.
Growing up in that environment didn't just make him "tough." It basically cauterized his empathy. He spent his teens bouncing between reform schools and the streets of New York, eventually working for his loan-shark uncles as an enforcer. He was a natural at it because, as he tells Evan Wright in the book, he simply didn't care about human life.
It was just business.
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The Vietnam "Correction"
When he got busted for kidnapping and attempted murder at seventeen, he was given a choice: jail or the Army. He chose the Army. But instead of straightening him out, Vietnam turned him into a professional killer. Roberts claimed he served in a long-range reconnaissance patrol (LRRP) unit, carrying out assassinations in Cambodia. While some of his military records are hard to verify—a common theme with guys like him—the sheer psychological damage he describes feels terrifyingly real. He returned to New York with a metal plate in his head and a complete lack of fear.
New York’s Disco King and the LSD Gags
Before Miami, Jon was the king of New York nightlife. By twenty-two, he was running some of the hottest clubs in the city, like Salvation. He wasn't just a bouncer; he was an impresario rubbing shoulders with Jimi Hendrix, Richard Pryor, and John Lennon.
But he wasn't exactly a "fan."
He’d do things like lace Ed Sullivan’s drink with LSD just to see what would happen. He treated celebrities like playthings. He was making a fortune, but the New York heat eventually got too high. After a business partner ended up dead and the Feds started sniffing around, he did what every smart criminal in the mid-70s did.
He moved to Miami.
The Medellín Cartel’s Secret Weapon
When Roberts landed in Florida in 1975, cocaine was still a "boutique" drug. It was expensive, rare, and sold in small amounts. Roberts changed that. He realized that the Colombians had the product but no way to move it efficiently.
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He teamed up with Mickey Munday, a mechanical genius and pilot, and Max Mermelstein. Together, they turned drug smuggling into a Fortune 500 operation. We’re talking:
- Secret airfields in the middle of nowhere.
- Advanced listening posts to eavesdrop on the Coast Guard.
- Homing beacons hidden in shipments to track them by sea.
- A "FedEx" style delivery system that moved billions of dollars in powder.
At his peak, Roberts claimed he was responsible for over half of the cocaine entering the U.S. He was making so much money he couldn't spend it fast enough. He bought dozens of racehorses, lived in a fortified mansion with mortars on the roof, and even kept a 200-pound cougar as a pet.
His bodyguard was a 6'6" professional wrestler nicknamed "The Thing."
Why American Desperado is Different
The book, co-written with Evan Wright (the guy who wrote Generation Kill), is a masterclass in true crime. Wright didn't just take Roberts' word for it. He spent years fact-checking the stories, interviewing old associates, and digging through FBI files.
What makes it so haunting is Jon's voice.
He doesn't ask for forgiveness. He doesn't pretend he was a "good guy with a bad job." He openly admits to being a sociopath. There’s a scene where he’s talking about picking up his son from school and being a "normal" dad, and in the next breath, he’s describing the most efficient way to dispose of a body.
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It’s that "Dr. Jekyll and Mr. Hyde" energy that makes the book so impossible to put down. It exposes the thin line between the "American Dream" and total moral rot.
The CIA and the "Get Out of Jail Free" Card
Eventually, the law caught up. One of his associates ratted him out in the late 80s, and Roberts spent five years on the run before being caught in 1992. But here’s the kicker: he only served about three years in prison.
How? Because he knew where the bodies were buried—literally.
He became a "secret government asset," helping the CIA and the Feds. He had connections to General Noriega and had played a role in the Iran-Contra mess. He was too valuable (or too dangerous) to leave in a cell.
He died of cancer in 2011, shortly after the book was released. He never expressed regret. He just viewed his life as a series of moves on a chessboard where he happened to be the king for a while.
What We Can Learn From the Chaos
Reading about Jon Roberts isn't just about the "glamour" of the 80s drug trade. It’s a reality check on how power and greed actually work. If you want to dive deeper into this world, start with these steps:
- Watch the original Cocaine Cowboys (2006): It gives you the visual context of Miami in the 70s and 80s.
- Read the book American Desperado: Don't skip the footnotes. Evan Wright’s fact-checking is where the real gold is buried.
- Look into the Iran-Contra affair: It provides the political backdrop for why guys like Roberts were allowed to operate for so long.
- Compare the narratives: See how Roberts’ stories differ from other "cowboys" like Mickey Munday to get a fuller picture of the truth.
The story of Jon Roberts is a reminder that the most successful criminals aren't the ones you see on the news—they're the ones who make themselves indispensable to the people in power.