My father sat in a quiet corner of the bar, holding a gin and tonic in one hand and a lighter in the other. His eyes crossed as he brought the flame to his cigarette; he puffed once, and went back to staring. He had been staring all night, looking out through the feathery darkness beyond the bar where dozens of young women bounced and twirled, rallying in daubed-on clothes.

He could see the dance floor in the middle distance, the sounds of Shannon and Culture Club bounding and rebounding. Then "Girls Just Wanna Have Fun" came on, and the effect of the first note on the crowd was like spray from a hose. A friend of my father's, a coke wholesaler with a pencil-thin mustache, threw him an apologetic look and jumped into the fray.

Anthony Edward Dokoupil was known for his on-the-job sanity. If he was working, he was happy and healthy, drug-free, focused, flowing, time bouncing off him. He had enough hair on his chest to float a gold chain, his belly was trim, and when he walked he swung his legs in loose semicircles, exuding a practiced magnetism, a put-on air of immortality. But this was the close of the 1984 pot season, the harshest of my father's long career. It was October, and he was back in Miami, tired and disappointed, his body quiet, all his energies turned inward.

He was angry at himself for letting cocaine use throw off his judgment; embarrassed about a botched stash house and a car crash; worried about those security cameras that must have caught him running through the lobby of a hotel with a box of money. All eighteen thousand pounds of weed had been sold, nothing lost, no one arrested. But by getting high on the job, he had broken the pirate code, nowhere written down but known by all. And now he had three months to sit and stew about it.

He was also expected home. He had a work-life conflict. It was a common thing for a family man, but it dragged my dad into a state of furious resentment. He loved us, would die for us, but go home to us? Sometimes it was asking too much.

So he sat in the Mutiny Hotel's private club in Coconut Grove and he drank, reaching the snapped lime in the bottom of another gin and tonic. The Mutiny Club was the capital of the American drug world, and though it was a generally safe place, it swam with suspicion and sex, emitting a palpable energy that attracted a romantic class of criminal. The most famous were the South American cocaine dealers, unsmiling businessmen who slid into the banquettes and hid guns in their baskets of dinner rolls.

My father's kind was rarer: the gringos, the grass dealers, the smugglers who tied off catamarans or cruising yachts, hair touseled, Top-Siders squeaking across the bow. As a public nuisance they were the buzz-muffle of an airplane over your house at midnight, the glow of brake lights on the highway at dawn. Where the cocaine kingpins murdered cops and bribed judges, the gentlemen of marijuana tipped their caps at the law and wished their competitors a happy chase.

My father was proud to be one of them. He ran stateside operations for one of the largest pot rings of the twentieth century. In all they sold hundreds of thousands of pounds of marijuana, and my old man distributed at least fifty tons of it. From New York City to Maine, and as far west as Colorado, people at that very moment could smoke my father's weed and feel the stress of the day wash clear. But six millions joints in a single load and no fun for the man who sold them? My father didn't think that was fair.

By 1:00 a.m. he had forgotten his woes, swallowed his conflicts, and slid off his barstool. He was celebrating his six million joints. He danced in white linen pants and what had to be one of the only short-sleeved V-neck sweaters in existence. Then, at about 3:00 a.m., he rented the highest room possible—ocean-facing, so no one could look in, and he and his friends from the escort service could be naked for days.

In recent years I've looked for a moment that defined my dad, and I return to this one again and again, largely because of its purity. After he landed at Miami International Airport he had a simple choice, a literal fork-in-the-road in Coconut Grove. He could go straight and find his family, or he could turn left and face trouble.

He turned. My father always turned.

If you smoked Colombian weed in the 1970s and 1980s, I owe you a thank-you card. You paid for my swim lessons, bought me my first baseball glove, and kept me in the best private school in south Florida, alongside President George H. W. Bush's grandkid, at least for a little while. But even though my father's vocation made all these things possible, the truth is I never really knew him, not as a man. He started a family the same year he graduated to loads of ten and twenty thousand pounds of marijuana, transported on freighters and tugboats from the northernmost point of Colombia to sailboats near the Virgin Islands, and ultimately to New York City wholesalers, vacation markets, and college towns along the East Coast.

But he vanished when I was about ten, and for most of my adult life I had only scraps of information about my old man. My mother almost never spoke of him, but I knew that he did drugs, sold weed, slept around, and bottomed out so completely that friends presumed him dead long before he was forty. My mother advised me to consider him dead as well. But I did the opposite.

How could I not? My father and I are separated by only an adjective—Big Tony, Little Tony—and when I was truly little, we toured Miami with our seamless tans and Lacoste swimsuits. My father liked daiquiris, virgin for me and extra shot of rum in the straw for him. He also liked girls, and he liked how approachable he was with a toddler sitting awestruck on the next stool over. He liked hostesses in particular.

Hostess: "Would you like to try our shrimp sampler?"

Dad: "I'd like to take a shower with you."

As a teenager, I began to build a theory of my father. A heartsick boy can compose a small, speculative history of manhood from a few photographs and a knife left behind in a drawer. Such was the style of my own imaginings. I told people my father was a cross between Tony Montana and Willy Loman, a big-time drug dealer, licking his wounds somewhere in South America. I could accept this version of him, and anyway, I needed it to survive. High school is hard enough without having to wonder about the blood you have, the brain you've inherited.

When I was twenty, I felt established enough to face the truth, so when a relative slipped me the number, I called my father. He refused to see me. After a few letters, he changed his mind, but then I refused to see him.

A few years later, in 2006, I changed my mind again. I found him near Boston, arriving unannounced after more than fifteen years and ringing the buzzer with my last name on it. He was living in a dreary apartment for ex-cons, the kind of place that brings down real estate prices and is quietly campaigned away by people with children. I rang the buzzer again. No answer.

He was in the Boston area because that's where one of Ronald Reagan's drug task forces decided to charge him. That, and because after his last marijuana job in 1986—an effort the DEA estimated at seventeen tons with a street value of more than $100 million today—he exploded his life. He lost his Mercedes, a boat, a condo, our family home, more than a million dollars in cash, and ended up working as a trash picker on Miami Beach. After his arrest, he had nothing but the system to take care of him.

The elevator opened and he walked out. He looked like a guy who had been on an all-night bus every night of his life.

"Are you Tony?" I asked.

"Yes."

"I'm Tony," I said.

"Okay."

"No," I said. "You don't understand. I'm Tony."

"Your name is Tony, too?"

"Yes. I'm Tony."

"Stop shitting me."

"No, I'm Tony."

No response.

"Your son?"

He bear-hugged me. He pushed me back into the wall. He was a smoker. He used Right Guard. He saved money on laundry. He was skinny except for his belly, which was fat in that way people appear to be fat when they're undernourished. His fingernails were thick and brown and yellow. Everything about him was raw.

His apartment was a studio with a shared bathroom down the hall. It was barren of furniture except for a bed with a body print on the mattress, night sweats in the sheets. There were a couple of hardback chairs, a desk. The walls were cluttered with Christian iconography; the surfaces were strewn with cigarette-scarred plastic cups.

He refused lunch, saying he couldn't handle crowds. So we went for coffee—his treat, he insisted—and then to his local library, where he introduced me to the bewildered librarians, their eyes assuming the same unfocused look of kids confronted with a chalkboard full of hard math. We were a head-scratcher, all right. I was fit, twenty-six, a graduate student in the big city. He was fat and unkempt, sixty, eyes wild in a way that made a person feel ill by association.

Less than thirty minutes later, I excused myself. I did not even ask him about marijuana. I consciously went unconscious about my father again, burying him so I could live a bit more.

It wasn't until I was pushing thirty, and a few years into a journalism career, that I was ready to talk to my father again. Peering over a reporter's notebook this time, I saw him as a character in a larger story about outlaws. In a digital age, hackers and Internet pranksters are the mantle bearers, people whose work is massively influential but rarely romantic, almost never sexy. There are no grand vistas, no beer commercial–grade photo ops, no tradition of carousing and womanizing, winning it all and losing it fast. There are no deathless pop songs about computer keystrokes.

This criminal-awe deficit, as I saw it, was the starkest in the weed business, where yachtsmen and beach bums like my father had been replaced by technicians and botanists. Bronze skin and wild, sun-bleached hair had faded into basement complexions and cowlicks. Where there was once the romance of foreign fields, leaky boats, and suburban stash houses there were now indoor "seas of green" and legal channels to market.

Weed is undeniably better today—every bud is a green chandelier of head-ringing crystals—but it's infinitely less interesting. Many of the old smuggler-dealers have come to the same realization. They see themselves as the last great outlaws, self-described pirates, heroically flouting a silly prohibition. They sure hope you'll agree, which is why more than a dozen of them were happy to talk to me.

But here I had a different motivation. See, I recently became a father myself. We had a boy, and it didn't take me long to see what I was up against. On my very first Father's Day, in fact, my infant son came home from day care with a preprinted poem, a trifle called "Footprints." Millions of dads probably got the same lines, and gave them no more than a sidelong glance before dinner. But the poem set off tiny sticks of dynamite behind my eyes.

It contains every immutable truth our society pushes—and I fear—about fathers and sons mimicking each other through the generations. It ends with the most painful idea of all, a repetition of the line "walk a little slower, Daddy, for I must follow you." I think it's the "must" that really stabbed my heart.

My father did not waver when I asked him to act as a tour guide to his past. We met at a different subsidized apartment, a federal home for the elderly and disabled, half a mile from Harvard University. It was still spare and grimy, adorned with the same Christian iconography and cigarette-scarred plastic cups. It may even have had the same liter of Diet Pepsi in the fridge.

We sat at the card table in the center of the room, where my father clapped his hands and smiled. The tour would need to hit New York and then Miami, he explained, and while he was open to itinerary ideas, he made the case for the Palace, the Plaza, and Gramercy Park, followed by Miami's Sonesta Beach Resort and of course the Mutiny Club.

I agreed to pay for it all. My father beamed as we shook.

Plenty of pot barons self-destructed in retirement, but no one did it quite like Anthony Edward Dokoupil. For weeks at a stretch he lived in luxury hotels, upended kilos of cocaine like bulk flour, and hired escorts by the squad. He found them in the phone book. One night my father started dialing, and the agencies somehow knew it was him. Every single one refused him service, for reasons I never mustered the courage to ask him about. And life was only just beginning to get ugly.

But two decades later, in the tasseled opulence of the Palace Hotel, my father moved like the chief conductor on a train, and when he leaned across the counter—raw-eyed and irregular despite his confidence—the check-in girl leaned toward him. To my surprise, their exchange carried on for a while. She laughed a little. Finally my father pushed off again, his legs working in those enlivening half circles, never straight lines.

"Seven hundred and fifty dollars a night," he said, eyes half open. "Fucking rip-off."

It was a similar scene at the Plaza, where we took a seat in the lobby, and I was sure we were about to be swept back outside. A waiter appeared, dropping menus in front of us, and stood there expectantly. The Diet Coke was six dollars. My father moved first.

"We won't be having anything today," he said, holding out the menus. The waiter's pen hovered above the pad. My father lifted his chin and managed to look down his nose at the waiter, who seemed to be losing air from somewhere in his lower back. I didn't even know declining to order was an option.

Our last stop of the day was Gramercy Park Hotel, where my father used to nettle the staff with endless late-night calls for more coffee and lubricant. The hotel had recently been redecorated, part of a quarter-billion-dollar renovation overseen by the painter and sculptor Julian Schnabel. The Times called the work "truly grand." My father sniffed around as though it were a ruined car.

"It's too bad they had to do this," he said, passing artwork by Andy Warhol and Damien Hirst. He paused in front of the baroque, heavy-beamed lobby and massive fireplace, dismissing it, likening it to "some place in Vermont." On the way out we passed beneath a humongous chandelier suspended by bronze chains. My father gave it a verbal middle finger. "Those crystals aren't even real," he said, and I dragged him out before anyone heard more. Later I looked it up, however, and it turns out he's right. Schnabel designed the chandelier with cast resin. My father knows his chandeliers.

For our first few days together, we were easy in each other's company. Dad was full of far-seeing criminal wisdoms and tourist board–ready exclamations. On Broadway he sauntered into the middle of the street and yelled down the canyon of buildings, hollering toward the horizon line: "I love being back in New York!" He started to make me angry only when his tone turned to one of regret. "Boy, I wish I had the money to live in the city," he said, as we walked a lane in the southeast corner of Central Park.

"You did have the money," I said.

"I did have the money," my father repeated. "But I had you."

"That's not where the money went."

"No, that's right. The money went like lightning. There was so much money I didn't know what to do with it."

A few minutes later my father patted all his stash spots, forgetting where he put his Social Security money. My father still gets federal checksbecause he paid taxes on two front companies and never faced charges for tax fraud. At last he found it and a twenty fell from his pocket as he paid for a two-dollar food cart coffee.

I had wanted my father to let me in on the story of his life. I had wanted to feel a shift from the ranks of those for whom the past is blank, the future uncertain, to those to whom all is known. I had wanted a simple window on who he was, and why he had left. I had wanted answers, is what I'm trying to say—but he seemed incapable of them.

I hoped Miami would be different. It was our shared city, after all, a shipwrecked fantasy where people ran away to live on squirt cheese and crackers, sleeping on their boats or way out in the ocean in houses on stilts. Our Miami was an exciting place to be a drug dealer or a little boy. It was barely a place at all.

In 1992, my father was charged with two counts of conspiracy to import and distribute seventeen tons of marijuana, and one count of criminal forfeiture for the $750,000 he made doing so. He pleaded guilty to distribution, and cooperated enough against his partners—according to a copy of a letter he sent his lawyer—to help get the other two charges dropped.

In all he served about a year and a half in custody: six months awaiting a court date (he had no money for bond), six additional months in a federal home for addicts, and six more for violating the rules of the home. He was lucky. Had the crimes he was busted for been committed a year later, he would have fallen under the mandatory sentencing guidelines of 1987—serving a minimum of ten years.

Our flight to Miami was my father's first takeoff since his extradition flight in 1992. Back then he was wearing an orange jumper, his feet chained together and his hands cuffed and then locked inside a black box, as though otherwise he might spontaneously procure and deal another seventeen tons of weed. This time, he wore an oversize blue knit shirt with Polo emblazoned across his heart. He began furiously chewing gum, mouth open wide enough to pop in a grape between each clench. His toes, exposed and wiggling in a pair of liquor giveaway flip-flops, looked as though they were recently recovered from an archaeological dig.

"Where's the stewardess?" he asked me. I looked up from a magazine to see my father hit the orange call button again, and again, and again. Finally a flight attendant came over, a concerned expression on her face, as if my father might be having a heart attack.

"Is everything okay, sir?"

"Could I have a coffee, please?"

The flight attendant looked annoyed but also wary.

"We don't have coffee prepared yet, sir. I'm sorry."

"Well, how long before the meal?" my father asked.

"No meal, sir." She gave him a wincing smile. "We'll be around with a drink cart soon enough. Meantime, would you like some peanuts?"

"Yes, thank you. And some coffee when it's ready."

My father downed the peanuts. When the coffee came he downed that, too. He'd assumed he'd get a plate of eggs, which is why he hadn't eaten in the airport. I could hear his stomach rumbling. He moved to hit the button again, and I grabbed his hand.

"They don't give you multiple cups of coffee anymore."

"They used to," he said, sinking back.

In Miami I got a glimpse of my father in his natural habitat, the place where he lived among his own kind, a group of righteous dope dealers that Timothy Leary once described as "the holiest, handsomest, healthiest, horniest, humorest, most saintly group of men that I have met in my life." When the legalization movement took off, my father was a supporter but his enthusiasm was tempered by a crisp, self-satisfied melancholy, an acknowledgment of the fact that legalization meant the final extinction of this cherished way of life.

But all that was far away as he was walking through Miami International Airport again, recalling the spirit and thrill of his last triumphant arrival, before it all went bad. As one of the nation's multi-ton dealers, he had felt like a hero to thirty million regular marijuana smokers, like their forty-year-old god, with a bag of money at his side and the promise of extraterrestrial bliss until every dollar was spent.

Our first stop was the Sonesta, where I had booked us a room. My father hummed happily to himself as we took his beloved fork in the road in Coconut Grove. The Sonesta Beach Resort was one of the swankier resorts on Key Biscayne, a breakwater island near Miami. The chickadee huts by the shore shaded conventioneers and wedding parties. ABC booked the beach for television specials.

It had been one of my father's favorite hangouts for partying and parenting alike. The poolside bartender, Geno, made a name for himself by pouring sweet rum into the straws of his piña coladas and daiquiris, and my father had frequently gone to see him or a deputy right away. But when we pulled up to the hotel, his mood blackened.

"What the hell is this?" he said.

At the front desk, we learned that this was the new Sonesta Bayfront, in Coconut Grove. I had booked it hastily, and then just followed the GPS to a place called "the Sonesta." My father, breathing Miami air, hadn't noticed we weren't following the old route. The woman at the desk gave us an address for the old hotel, and we got back into the car and drove over. We were not prepared for what it would look like. It turned out that the Sonesta Beach Hotel had been on an epic slide of its own. It was half destroyed by Hurricane Andrew, which left it windowless and closed for more than a year, and it never fully recovered. It changed hands a few times, was sold and resold. Big rehabs were hatched. And then, just a few months before we got there, the Sonesta was demolished, the tennis courts hacked up, the beach brushed clean.

When we arrived at the site, it was just a pile of rubble. My father put his hands on his head, and said, "Oh no. Oh no. Oh no." He stepped out of the car before it stopped rolling and, in his flip-flops, slipped in the construction muck as he walked to a perimeter fence and peered in at a mud pit. The picture could have run on front pages as a natural-disaster photo: Man in grief. It was not just the building they had flattened. It was my father.

We returned to the new Sonesta, which was first-class in every way, but my father couldn't help notice that it had no poolside bar, no Geno waiting with a shot of rum. There was a business center, but no beach for father-son Wiffle ball, and I didn't see anybody wearing banana hammocks into the pool.

For dinner we went to the rooftop restaurant, where we had a view of Biscayne Bay, which bristled with dozens of sailboats in silhouette. It was Sailboat Bay, my father suddenly realized, almost the same view as from the upper rooms of the Mutiny Hotel, where he'd had so much fun he never came home.

That meant the Mutiny was right next door—but when my father looked, his face fell again. The original hotel and clubhad fallen on hard times, changing hands and suffering a series of reversals. The property was closed for most of the 1990s, and when it reopened the club was gone and so were the rooms that once had functioned like themed porn sets. The "Gypsy Caravan," "Hot Fudge," and "Outer Space" rooms, along with a hundred and thirty-five other scenes of vigorous American history, were redone in a "British Colonial" motif and sold as condos.

My father turned away from the rail and found a poolside lounge chair, where he lay down, throwing his hand over his face in a death-to-sunlight fashion. After I ordered, he came over to join me, adding a white wine to the tab. He was silent.

"All the good old fucking days are gone," he said at last, his voice quavering. "This is goodbye to the best times in the world."

The next day in the car my father volunteered that he was going to heaven. He says his was a victimless crime, and that if he had the chance to do it again, he would live his life exactly the same way.

"All of it?" I said.

"In a second," he said.

We had driven over the causeway to find the Monkey Jungle, one of the only father-son haunts we had left to visit. It was gone, another casualty of Hurricane Andrew. So I headed down an interesting side road, passing dry pines, then mangroves, then a greedy waterline that left just a few feet of land and a row of colorful shacks, fishermen's lean-tos and the like. A spray-painted school bus threw shade on some old men selling drinks. We bought Diet Cokes and walked out on a dock, which yielded a perfect view of the Miami skyline.

My father started in again about money and wishing he could live in Miami, and I realized that he was enjoying this trip too much. He loved the high life. He loved to lose it. His own father went crazy because as a bombardier in a B-24 over Europe, he could never see what happened after the bombs fell. But my father didn't give a shit about the damage that remained.

"Do you think there was something romantic about pissing your life away?" I asked him.

"Looking back, it wasn't romantic."

"Yeah, I know. Sure. That's what you're supposed to say. But seriously. Was it literary for you to live the low life?"

"Tony," he said, with a shrug, "I've liked my life. I liked the drugs and the girls and the money. I liked living like a pirate, outside the real world, never doing anything but dabbling and talking."

"You wouldn't change a thing?"

"I wouldn't have walked out on you."

"But you had that chance. You made a choice."

"I chose drugs."

"Yes, you chose drugs. So you can't go through the motions of regret, not if you don't really feel them."

"I regret…" He stopped. "I regret that I pissed it all away."

"Bullshit," I said. "Obviously you don't. You had to piss it all away or you wouldn't be an outlaw."

"That's good, Tony. You're a pretty smart kid, you know that? I think you hit it on the head."

We stood in silence.

"I also think I was angry inside. You think that's bullshit?" he asked.

"I think you made your choice."

"I thought I was going to die not being with you. It felt like a stone in my stomach, like having a rock inside me, a heavy rock, and the dope didn't take it away, and the prostitutes didn't make it better."

"If it was so bad, then why didn't you stay with me?"

"I did the coke to dull the pain."

"If the pain was so bad, why not alleviate it by staying?"

"I have no explanation. I don't know," he said. "I know the coke didn't work."

[BREAK]

We parted ways again in New York. I headed for my family in Brooklyn, he headed to Chinatown for an all-night bus to Boston. That night, for the first time, I looked at the darker side of my father's story without looking away. I glanced through pictures from the trip, toggling between the reality of the image, my father's reality, and my own. To everyone else who saw him in Miami, he was surely a bum. To me, he was a bum who was once a millionaire, and that's a very different thing.

Or maybe it is just that I have my father's eyes, not their blue tint but their double vision. I see the horror; I see the glory. I am a boy abandoned by a father who still describes his time drug-dealing, and not his time raising a son, as "the most exhilarating and wonderful years of my life," and "absolute heaven." I am an adult who understands my father's reasons, even if I do not find them compelling. When I look at my own son, as my father must have looked at me, I think my father is heartless for leaving. When I look at the man who left, I think he is human for doing so.

But most of all, I realized—on that last day in Miami—that I didn't lose my father to drugs, or addiction, or anything quite so shameful. I lost him to work, to passion, strange to say: a drive not so different from another man's drive to put his name on a door, his stamp on a building. Evidence of fatherless children is everywhere, once you become alive to life's trade-offs, and you learn that there is no balance, none possible, and for many, my father included, none really desired.

"I loved you," my father said at one point, interrupting one of my interrogations. "I would die for you. But I was what I was. I was a scammer and a smuggler and I was a good one. That's it. That consumed me. I never thought about doing anything else."

I love this about my father. It means everything, in fact, because for as long as I can remember, I've been afraid of becoming him. I thought I would lose control and go skidding into his state of being. But my father wasn't out of control. He wasn't driven by demons. If he chose his life, I can choose mine.

Tony Dokoupil is a senior writer for NBC News. He lives in Brooklyn. The Last Pirate: A Father, His Son, and the Goden Age of Marijuana, from which this story was adapted, is on sale now.

Tony Dokoupil Tony Dokoupil is a co-host of "CBS This Morning." Previously, he was a CBS News correspondent and a "CBS Sunday Morning" contributor.

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