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APRIL 2008—MIAMI

EVAN WRIGHT (E.W.): During a break in the Heat versus Pistons game at Miami’s American Airlines Arena, an announcer informs the crowd that a “very special celebrity” is in the house. “Ladies and gentlemen, we have Jon Roberts, Miami’s original cocaine cowboy, with us tonight.”

Live images of Roberts seated in the arena splash onto the screens in the arena: a physically fit sixty-year-old with silver hair combed straight back. Unaware that he is being filmed, Roberts gazes expressionlessly. Deep-set eyes give his face a wolfish, predatory appearance. Fans seated near him stand with their camera-phones and take aim. Roberts notices his image on the screens and offers a pained okay-you-got-me grin. He puts his arm on his eight-year-old son, Julian, seated beside him. Julian ducks his head into his father’s shoulder but peeks up, grinning, as cameras flash. His dad is the biggest star in the arena.

Little more than fifteen years earlier Roberts was a fugitive. His face was featured on FBI most-wanted posters at U.S. post offices across North America. He fled Miami after the U.S. government labeled him as top “American representative” of the Medellín Drug Cartel and charged him with overseeing the importation of billions of dollars of cocaine. Roberts and a small band of American partners had created a veritable FedEx of drug smuggling. They employed secret airfields, listening posts to eavesdrop on Coast Guard communications, and sophisticated homing beacons for tracking cocaine shipped by sea that stymied the U.S. government for nearly a decade. That part of Roberts’s story—and the outrageous life he led that epitomized the excesses of Miami’s cocaine-fueled boom of the 1980s—was told in the underground hit documentary Cocaine Cowboys, released in 2006.

Key aspects of Roberts’s extraordinary criminal life remained untold—his rise in a powerful New York Mafia clan, the murders that prompted his exile to Miami, his involvement with a CIA official that led to a secret plea deal with the government.

Through it all, he possessed an asset not typical of admitted killers: charm. A man who did business with Roberts in his New York Mafia days—and later joined the priesthood as a result of the experience—told me, “Jon was extremely likable. He was fun to be around. Underneath that was a person capable of very bad things. He is an extreme dichotomy of good and bad. He is a very old story, Dr. Jekyll and Mr. Hyde.”

Roberts’s frankness about himself—usually blended with a sly, sardonic humor—can be disarming. In a phone call before we met to discuss telling his full story, he said, “I might be a sociopath. Most of the time I’ve been on this earth I’ve had no regard for human life. That’s been the key to my success.”

I ARRIVE in South Florida the spring of 2008 to begin interviewing Roberts for this book. He insists that I stay with him and his wife, Noemi, and son, Julian, at their house in Hollywood, Florida. He insists that I not rent a car. He’ll pick me up. He’ll drive, always. “I don’t ever want to be in a car with somebody else driving it,” he explains.

Jon’s accent is New York, but not the tough-guy dialect of the streets. He speaks an urbane New Yorkese, like Michael Douglas’s Gordon Gekko in Wall Street. We do many hours of interviews in Jon’s car, visiting old haunts—bars, smugglers’ docks, murder scenes—with time out to pick up Julian at school and shuttle him to playdates and hockey practice.

When Julian is in the car, Jon drives at the proper speed and questions him about school, like any other involved parent. When Jon and I are alone in the car, he reverts to old habits. He seems to drive his car, a late-model Cadillac, at only two speeds, 75 mph on surface streets and 110 mph on freeways. As he darts in and out of traffic and squeals out of parking lots, driving with Jon feels like being dropped into a car-chase scene in a 1970s movie. I glimpse the rearview mirror, expecting to see elaborate car crashes in our wake and flashing red lights. But Jon is a precise high-speed driver, never reckless. Rocketing toward a parking space, he flicks the wheel with one hand and backs in. He always parks his car facing out, primed for a quick getaway.

Jon’s home is an expansive Spanish modern, set against a lake on the Inland Waterway. Before we enter, he clips blossoms from a jasmine vine, then places them in a vase in the front hall. A friend from his New York days tells me that Jon has always liked flowers. “In his apartments he always had a bowl of water with a gardenia blossom floating in it.”

Jon’s hospitality is obsessive. Before my arrival he phoned me on a morning when I happened to be eating blueberries. Now a fresh basket of blueberries waits for me in the refrigerator. Every time I visit there will be blueberries.

In the Roberts household, Jon does the cooking—French toast for breakfast, pasta and baked fish for dinner. Unless there is an NBA game on, or a new episode of Two and a Half Men—his favorite show—meals are eaten at the long, plank-wood dining table. Noemi is responsible for setting it.

She is an energetic presence, thirty years younger than he. Noemi is African on her father’s side and Hungarian on her mother’s. She and Jon met shortly after she arrived in America, when she was training in a Miami park for a triathlon. There is an athletic bounce to her movements, and she speaks in an exuberant, bubbling accent—not always easily understood. She pulls me aside before my first dinner in the house and says, “I adore Jon. But the day I met him, he touched me and my body went numb, because his energy is black. Jon is not human. I love him, but I live as his prisoner. I cannot leave him because his evil is magnetic.”

Overhearing his wife’s commentary, Jon offers a Father Knows Best laugh. “Please, Noemi. You’ll spoil his appetite.”

Jon’s older sister, Judy, who lives nearby, is a frequent dinner guest. A graduate of Emerson College, Judy was a personnel director at a large New York company while Jon pursued his criminal career. After the birth of Julian (by Jon’s previous wife), Judy moved to Florida to help raise him. In her mid-sixties, Judy is slim and stylish. At the dinner table she speaks in a calming voice, directed at Julian when he mumbles about his schoolwork, then at Jon when he shouts at Julian for mumbling. “Let him speak in his own voice, Jon,” she scolds.

Jon shakes his head and sighs, surrendering to his sister.

Julian smiles. You get the idea that agitating Jon is something he likes.

After dinner Jon and Julian shoot hoops in the driveway. When Julian runs for a layup, Jon grabs him and swings him in the air, closer to the rim. Julian makes the shot, and Jon releases him. Jon says, “He’s a monster. He beats kids twice his size.”

There are three dogs in the house. (“My first ring of defense for an intruder,” Jon explains.) The biggest is Shooter, a 150-pound Presa Canario—a fighting breed banned in parts of the country due to the dogs’ well-deserved reputation for fatally mauling humans. Shooter follows Jon everywhere and growls if I make a sudden movement. “He’s very protective of me,” Jon says. “Don’t ever lift your hands high. Shooter doesn’t like that.”

“What will he do if I raise my hands?”

“Just don’t do it. Trust me on this one, bro.”

There is an awkward moment when Jon walks me into the guest room, where I’ll sleep. The carpet is smeared with a five-foot-long trail of blood, bones, and animal guts. Jon curses. It’s the neighbor’s cat, whom Shooter has eaten and vomited up. “What a shame,” Jon says, delicately scooping pieces of cat into a trash can. “I love cats.”

Shooter has also killed two dogs on the block, a pit bull and a chow. Recently, he chased a Haitian gardener into a tree for whistling at Noemi. At sunset, when Jon and Noemi take Shooter for a walk, neighbors greet them with frozen smiles and retreat behind their doors. “Unfortunately, if a dog challenges Shooter, he will kill him. It’s his nature,” Jon says.

Late at night Jon scrubs the house from top to bottom. Judy says he has always been neat. His prison reports state that as a federal inmate, he “went beyond the call of duty in maintaining the sanitation of his sleeping area and the kitchen.”

As he mops the floor one night, Jon explains the secret of a perfect shine, which he learned in prison. “Fill the bucket with ice, put the wax on when it’s almost frozen. That’s how you get the shine.”

I joke that he cleans the house like it’s a murder scene. Jon tilts his head back and laughs, while keeping his eyes on me. The eyes don’t laugh. Jon is a formidable presence, even in his sixties. Though no taller than five foot ten, he wears tight shirts that show off a shredded and always deeply tanned physique. A few years ago, after his release from prison, Jon was involved in a petty altercation on the street. Police were called, and Jon found himself in the back of a squad car. With his arms cuffed behind, Jon kicked out the back window and escaped. When the two officers attempted to rearrest him, Jon badly beat one, and several more were called to subdue him with a Taser. “I overreact sometimes,” Jon explains. “But I don’t want to do that anymore, because of my son.”

Jon avoids talking about his past in front of Julian. But the dark side of Jon’s life intrudes. When Jon sends me to the store in his car to buy milk, I reach for sunglasses under the armrest—and a loaded .45 falls out. Later Jon shows me the locations of two guns with silencers, sealed in plastic bags and buried not far from his house on somebody else’s property. He says, “I’m not saying these are my guns, but now you know where they are, in case I ever tell you I need one. You can dig them out with your fingers.”

While Jon keeps some secrets from Julian, he doesn’t hide the positive attention he receives for his gangster past. Hollywood übre-agent Ari Emanuel calls frequently to discuss Roberts’s deal with Paramount Pictures and Mark Wahlberg, who plans to portray him in a film. During one such call, Noemi says, “See. People come to Jon because he is evil. Mr. Emanuel and the movie star Mark Wahlberg worship the power my husband has. They wish they could have even one pinkie full of the evil that Jon has.”

Julian tells me, “Mark Wahlberg is going stay at our house. My dad’s the cocaine cowboy.” He adds, “Akon* wrote a song about my dad.” And Julian sings, “ ‘Stone cold killer with a pocket full of triggers, movin’ that shit by the pound, boy. Better watch out, my dad’s the Cocaine Cowboy.’ ”

Later in the week I enter Jon’s home to find Akon himself sitting in front of the TV with Julian playing video games. Jon claims that Snoop Dogg, 50 Cent, and Lil Wayne have all made pilgrimages to visit him. As Julian explains, it’s “because my dad’s an original gangsta.”

Jon and I begin our interviews each morning at eight-thirty, after he drops Julian at school. We sit in the living room by a window overlooking the swimming pool. Jon’s recall of names, dialogue, and small details about people is impressive. Due to the notoriety of Jon’s family and his own criminal career, there is a vast newspaper archive chronicling key events of his life—his name first appeared in The New York Times in connection with a murder shortly after his twenty-first birthday. The format of this book was originally intended to be strictly “as told by Jon,” but when some of the stories he told stretched my credulity—from his tales of hanging out with Jimi Hendrix to his detailed account of committing a murder with a man who later became a high-ranking CIA officer—I sought other sources. Their voices are included here and serve to corroborate or at times challenge Jon’s version of events.

Jon’s language is direct, simple. He generally speaks in what could be called community college–level English, but when recalling past events, he often switches to a syntax of double negatives and ain’ts that’s closer to the street. Like many people, when Jon tells a story from the past, he often slips into the present tense for the more action-oriented sequences. In writing the book, I occasionally changed the order of the narrative and cut for length, but I didn’t invent flowery language or put false observations in Jon’s mouth. In some instances, improper grammatical constructions used by Jon are preserved to maintain the authenticity of his voice. It is his story.

In pop culture the rough-edged but almost lovable gangster has almost become a stock figure. Jon does not fit that image. His self-portrait of violent and predatory behavior is far too frank. His is a story that deconstructs the myth of the honorable gangster and along the way does some serious damage to idealized views of American innocence. Jon thrived as a criminal by being a keen observer of people, and his narrative is filled with cutting portraits of the corrupt politicians, dirty cops, fallen celebrities, rogue CIA agents, and other members of the decadent ruling class who populated his world. His story ultimately stands as an unsettling social history of America, from the 1960s through the 1990s, as told from the perspective of a largely unrepentant criminal.

Jon assures me he has no interest in morality, but his conversations always turn to the moral puzzle of who he is. He begins our interview, saying, “If there is one thing my life has been about, it’s the idea my father taught me when I was a boy: Evil is stronger than good. If you have any doubt, pick the side of evil. Those are the morals I lived by. It’s how I got power in different situations. Evil always worked for me. My life is proof that my dad was right. But I hope he’s wrong, too. For my son’s sake. I don’t want to raise my son like my father raised me.”

“I don’t like some of the things my son hears about me from other people. I think it’s strange that we go to Miami Heat games, and when they announce I’m there, everybody applauds, like I’m a hero. If people knew the truth about me, I wonder if they would still be applauding my name.

“When I was born, America was a very straight country. A guy like me wouldn’t have been applauded back then. But I hear the music my son listens to, and it’s all garbage—this gangsta crap—where the singer doesn’t even talk English. This is what people value today, so they probably will still applaud me. I don’t care what they do. The important thing is my son will know the truth about me.”

* The Grammy-nominated hip-hop performer and producer.

The lyrics to the song “Cocaine Cowboys,” written by Akon and performed by Akon and DJ Khaled, do not include the line “Better watch out, my dad’s the Cocaine Cowboy.” Julian added the line after listening to an advance copy of the song Akon gave to Jon.