Jon Roberts: American Desperado Excerpt
Credit: Photograph by Jamie Chung

Shortly after Jon Roberts, the convicted drug smuggler profiled in the 2006 documentary 'Cocaine Cowboys,' invited me to stay at his house to work on his memoir, I woke to the sound of gunfire. I was in the guest room of the home, nestled in the ritzy lake section of Hollywood, Florida. Moments later, Roberts entered the hall, wearing shorts and an open shirt that revealed an almost freakishly ripped physique, especially given his age, 61 at that time, in 2009. "Nothing to worry about," Roberts said, sweating profusely from his face. "Just some birds."

He explained that a flock had descended on him – perhaps even initiated some sort of coordinated attack – while he shook out his bedroom carpet on the balcony overlooking the lake. The gunfire I heard was his attempt to scare them off. The birds, he believed, were "Satan throwing me a sign. That would be him saying, 'Hey, bro. This is to remind you I got my eye on you. You'll be mine soon.' "

Some 15 years earlier, Roberts had been a fugitive, having fled Miami after the U.S. government tagged him the "American representative" of the Medellín cartel. Roberts and his partners had created a veritable FedEx of drug smuggling. They employed secret airfields, listening posts to eavesdrop on government communications, and infrared homing beacons to track air drops. For nearly a decade, they evaded the authorities. The government conservatively estimates that Roberts and his crew were responsible for $15 billion worth of cocaine that entered the U.S. in the 1980s.

After doing a stretch in federal prison, Roberts returned to Florida and lived in obscurity until the release of 'Cocaine Cowboys' turned him into a surprise celebrity. Roberts was caught off guard when his attendance at a Miami Heat game was announced and drew a standing ovation from the crowd. The documentary had spun Miami's cocaine-fueled decade of mayhem into a mythic tale of outlaw glory, and Roberts was a charismatic presence, speaking in a streetwise but genial voice even as he told of beatings and murders he'd had a hand in. Soon Paramount was negotiating for his story rights, and Mark Wahlberg was angling to play him.

After I arrived at his Florida home to work on the book, Roberts proved to be an attentive host, a charming storyteller, a fantastic cook, and an utterly disturbing human being. It wasn't just the early-morning soliloquies on Satan or the guns with silencers sealed in plastic bags and buried not far from his house, which he made sure to show me – "in case I ever tell you I need one, you can dig them out with your fingers" – that were so jarring. It was also the principles he laid out to me for the book – principles that had made him effective not only as a criminal but also as a topflight racehorse owner and trainer and, earlier in his life, a Manhattan nightclub impresario. The secret to his success, he explained, lay in a diagnosis once given to him by a mental health specialist. "I'm a sociopath. Most of the time I've been on this Earth, I've had no regard for human life. In my world, that was an advantage. Inflicting pain and using fear were tools I used to get my way."

Roberts was born with the surname Riccobono. His father, an illegal immigrant from Sicily with ties to America's first truly national Mafia leader, Lucky Luciano, was a midlevel capo who ran gambling and loan-sharking operations out of black bars in New Jersey. When Jon turned five or six, his father began taking him on collection rounds. "My dad put me in back while he and his bodyguard drove around looking for deadbeats who owed him money." The boy internalized what he saw. "My dad always hit people with objects – a bat, brass knuckles, the end of his gun. His main philosophy of life was 'Evil is stronger than good. If you need more power in a situation, pick the most evil way, and you will come out on top.' "

As if to illustrate his point, Roberts's father shot a man to death in front of him – not as part of a crime operation, but simply because the victim would not get out of his way on the street. His father was deported in the late 1950s during a federal crackdown on the Mafia, and his mother changed Jon's last name to Roberts to sever his ties with his father's legacy. A short while later, his mother died. An orphan at 13, Roberts was raised briefly by his stepfather, but when he proved unruly, he was placed in a boys home.

Though it was his father who gave him his guiding philosophy on the power of evil, it was a loose-knit gang of mostly Italian teenagers in Teaneck, New Jersey, who introduced him to the thrills of street violence. I'll let Jon describe that period of his life in his own words.