The Last Pirate: A Father, His Son, and the Golden Age of Marijuanaby Tony Dokoupil
A haunting and often hilarious memoir of growing up in 80s Miami as the son of Big Tony, a flawless model of the great American pot baron.
To his fellow smugglers, Anthony Edward Dokoupil was the Old Man. He ran stateside operations for one of the largest marijuana rings of the twentieth century. In all they sold hundreds of thousands of pounds of
A haunting and often hilarious memoir of growing up in 80s Miami as the son of Big Tony, a flawless model of the great American pot baron.
To his fellow smugglers, Anthony Edward Dokoupil was the Old Man. He ran stateside operations for one of the largest marijuana rings of the twentieth century. In all they sold hundreds of thousands of pounds of marijuana, and Big Tony distributed at least fifty tons of it. To his son he was a rambling man who was also somehow a present father, a self-destructive addict who ruined everything but affection. Here Tony Dokoupil blends superb reportage with searing personal memories, presenting a probing chronicle of pot-smoking, drug-taking America from the perspective of the generation that grew up in the aftermath of the Great Stoned Age.
NBC News senior writer Dokoupil offers a gripping examination of his longtime marijuana-dealing father, as well as a researched look at the evolution of American narcotics laws. In the early 1970s, Dokoupil’s father, also named Tony, dropped out of graduate school to deal marijuana. The charismatic “Old Man” was quickly able to make the necessary connections and, with support from a woman he married, rose to a position of power on the East Coast drug circuit, eventually setting up base in Miami. According to Dokoupil, who grew up in 1980s Miami, his father’s constant need for excitement and hedonistic tendencies coupled with an ever-changing drug market led to his eventual downfall. Drug and prostitute binges, risky schemes to smuggle drugs across borders, shady associates, and the frequent mistreatment of his family (including throwing a knife at his wife and leaving his four-year-old son alone at a hotel at Disneyworld) eventually led to the family falling apart and Tony’s incarceration in 1992. Dokoupil’s sharp eye for detail makes for a lively and often moving narrative full of cinematic scenes and snappy dialogue. Dokoupil draws on his experience as a reporter to deliver an unflinching and detailed look at a criminal family’s life. (Apr.)
Vanity Fair “Hot Type” Pick, April 2014
GQ “Best in Culture” Selection, April 2014
Esquire “Passage of the Week” Selection, April 2014
"A probing, exuberant memoir about the history of the American drug economy, the ambitions and failures of politicians and outlaws, fathers and sons...a fascinating tale about the wreckage of addiction and the shadow side of the American dream."
-Domenica Ruta for The New York Times Book Review
“Dokoupil’s early childhood wasn’t exactly ordinary. It was a hedonistic life of beach resorts, yachts and private schools paid for with drug money–a million of it stored in coolers and buried in backyards around the country…Now in his thirties with two children of his own, Dokoupil mines his father’s memories and his own to produce a funny, beautifully written and sometimes unsettling personal narrative that is entwined with the story of marijuana’s dramatic ascent in the United States over the last three decades.”
“At the height of the 1980s' war on drugs, the scoundrels who defied Reagan by smuggling in tons of pot viewed themselves as latter-day pirates who lived by their own code of ethics and, apparently, the lyrics of Jimmy Buffett songs. Four years ago, journalist Tony Dokoupil tracked down one of the era's most infamous outlaws: his own father…Get a contact high from the golden age of pot.”
“The book is fascinating…more than just a rollicking, dope-saturated yarn. Yet the book is also a rollicking, dope-saturated yarn.”
—Salon (Book of the Week)
"A meticulously researched history of America's rocky relationship with marijuana... It's also a memoir about a son struggling to process his abandonment by a dope-obsessed, deadbeat dad who happened to be a key figure in all that smuggling, distributing and dealing. And, as those first two descriptions suggest, it's the kind of narrative that screams out to be adapted into a gritty, layered cable TV drama with a prime-time slow on AMC or FX."
—The Washington Post
“The Last Pirate” is an astonishing account of a marijuana millionaire’s hedonistic life—one so stuffed with cash that he literally buried a million dollars worth of bills in ice coolers on Long Island and in New Mexico. Anthony Dokoupil’s story of incredible excess is told by his son, NBC News senior writer Tony Dokoupil…Dokoupil’s prose is as artfully vivid as the tale itself and explicit about the sins of the father who abandoned him.
—New York Daily News
“He wrote the book to explain his own father, who was smart and self-destructive and finally was arrested in 1992. As a writer, the son saw a larger story about my father's generation and the world he lived in. The rise and fall of a certain kind of outlaw who no longer exists.”
"While the author does show how the drug culture has grown up and settled down, his father's story and his own outshine the large-picture history and bring it up-close and personal, with humor, sensitivity and a keen eye for the surprising detail."
“NBC News senior writer Dokoupil offers a gripping examination of his longtime marijuana-dealing father, as well as a researched look at the evolution of American narcotics laws… Dokoupil’s sharp eye for detail makes for a lively and often moving narrative full of cinematic scenes and snappy dialogue. Dokoupil draws on his experience as a reporter to deliver an unflinching and detailed look at a criminal family’s life.”
—Publisher’s Weekly (Starred Review)
“There is a pseudoheroic, merry-band-of-pirates tone to these often-hilarious adventures in the drug business during the Reagan era. Dokoupil recounts how the smuggling and distribution business ran and contextualizes it within the “Great Stoned Age.” Partly the history of a generation, yet very much a family story…though there are no heroes, readers owe the author thanks for this well-told, ironic, and gripping story.”
“With its unmistakable ring of truth, The Last Pirate strips away the self-serving blarney about big-time pot smuggling of the seventies and eighties to tell the sad but compelling story of a narcissist who, with a notable lack of self awareness, wrecks his family and his own life to fulfill his delusions of grandeur. In reporting on and coming to terms with his father’s colorful and destructive past, Tony Dokoupil has added remarkably to the nonfiction literature of the drug business.”
—Bruce Porter, author of Blow: How a Small-Town Boy Made $100 Million with the Medellin Cocaine Cartel and Lost it All
“The Last Pirate is crazy brilliant. Both hysterically funny and irresistibly disturbing, I could not stop reading it. The TV show Weeds is a nursery rhyme compared to the real-life grit, danger, and devastation of this family’s story. But it wasn't only the mayhem that I loved. Tony Dokoupil also shows us how a son can forgive and accept a father who really doesn’t make it easy.”
—David Sheff, author of Beautiful Boy
Looking to cast light on a lost age of outlaw heroics, NBC News senior writer Dokoupil digs into the adventures of a major drug smuggler of the 1970s and '80s: his father. If you smoked marijuana on the East Coast after President Richard Nixon declared war on drugs in 1972, chances are "Big Tony" Dokoupil had a hand in getting it to you. Highly intelligent and entrepreneurial, the senior Dokoupil was a college dropout and recovering junkie when he discovered that dealing pot was a highly effective way to earn lots of money quickly. Within a few years, from bases in Miami and the Caribbean, he was helping to smuggle hundreds of thousands of kilos of Colombian Gold all the way north to New England and as far west as Colorado, until a cocaine habit he developed clouded his judgment and sent his life and career into a tailspin in the mid-1980s. Once a self-described "Pirate King" at the apex of Miami's drug scene, by the early '90s, Big Tony was a paranoid wreck, sleeping under bridges, assumed to be dead by his former friends and family, trying to remember where his buried treasure went and waiting for the Drug Enforcement Agency's ax to fall. Though Big Tony was more an idea than a steady presence in his life, Dokoupil the younger, now a father himself, struggled with an intense ambivalence about his dad. A bit of a delinquent himself in high school, Little Tony was saved, mostly, by a talent for baseball that earned him a college scholarship, but he remained haunted by the ghost of his father in his genes. "I've tried to write a broad chronicle of marijuana-smoking, drug-taking America rather than a closed circle of family woe," he writes. While the author does show how the drug culture has grown up and settled down, his father's story and his own outshine the large-picture history and bring it up-close and personal, with humor, sensitivity and a keen eye for the surprising detail.
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Read an Excerpt
Excerpted from the Hardcover Edition
Miami, Florida, 1984 Milford, Connecticut, 1970–1975
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, 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 to and fro in daubed-on clothes.
He could see the dance floor in the middle distance, slightly elevated toward an already low ceiling. The sounds of Shannon and Culture Club bounded and rebounded. Then “Girls Just Want to 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. Even sitting down he pumped out so much animal energy that my mother used to say he had shark’s blood: immune to disease, fearsomely alive, buoyant so long as he kept moving.
It 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 some incipient late-night needs throw off his judgment; embarrassed about a botched stash house and a car crash; worried about 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 he had broken the pirate code, the bylaws of his life, nowhere written down but known by all, and he had three months to sit still and stew about it.
My father was also expected home. He had a work-life conflict, a problem so mundane that it was hardly a problem at all, and might even be a blessing. But it dragged my father 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 a private club in Coconut Grove and continued to drink, reaching the snapped lime in the bottom of another gin and tonic, not even looking up when a familiar smell drifted into his range. When a joint burns it gives up the ghost of every day it grew in the equatorial sun, every bright and gorgeous ray of sun, every grain of soil. The smoke bounces off the back of the throat and envelops the nervous system, washing through the smoker like a warm tide.
From the mid-Atlantic states to Maine and as far west as Colorado, people at that very moment could smoke my father’s weed and feel their socks loosen and their scalp tighten and all the stress of the day wash clear. Usually my father loved to picture the end consumer. The best man with the full coat pocket. The college kid with the stash in his glove compartment. Even the high schooler, yes, the kid on drugs, the mop-top with the Kinks on the stereo, a towel stuffed under the door, and a can of Glade in his hand.
Six million joints but no freedom for the man who sold them?
My father didn’t think that was fair.
He thought of his partner Bobby, a Brooklyn garbageman who retired into marijuana sales, out making Manhattan his playground. He thought of Charlie and Willy, his contacts in the Caribbean, near the bottom of a Heineken, their hearts like steel drums, feet stomping seashells at some dockside bar. Finally, he thought of the everyday gawkers outside on South Bayshore Drive. People in rental cars nosing out of the lot at Dinner Key. Teenagers in Mohawk haircuts, kid siblings in Mickey Mouse ears. Moms and dads in pleated shorts, striped shirts, and leather sandals. People with such lives looked south on Bayshore and through tired eyes they saw it, rising brightly above a series of thatched outdoor bars and a glowing cobalt swimming pool: the Mutiny Hotel at Sailboat Bay, the scene of my father’s sulk.
The Mutiny was the start of the American drug world, and though it was a generally safe place it swam with suspicion and sex and incipient violence, a palpable energy that attracted a romantic class of criminal. The most famous were South American cocaine dealers. They were unsmiling businessmen who slid into the banquet tables against the wall and hid a gun in the dinner rolls. My father’s kind were rarer: the gringos, the grass dealers, the smugglers who tied off catamarans or cruising yachts, hair tussled, Top-Siders squeaking across the bow. America used to produce men like these, pool-hall handsome, caddish, light-minded men, the source of America’s fun if not her pride.
My father was proud to be one of them, gathered into what looked like a four-star restaurant merged with a disco and crossed with a Hong Kong sex lair. He wore white linen pants and what has to be one of the only short-sleeve V-neck sweaters in existence. The carpet beneath his slip-ons was blue and shaggy. By the door to the pool, on the path to another bar, a single vulnerable orchid performed in a pin spot of light. For aristocrats there was a harpist in a G-string, replaced at midnight by roving jugglers and mimes, and finally topless dancers. What did it feel like to walk into such a world, a young father with an envelope of coke in his pants, a bag of cash at his service? The pull of other worlds weakened and then vanished, a feeling like flying, like staring out the oval window of an airplane the instant it leaves the land where you were born.
By 1:00 a.m. my father had forgotten his woes, swallowed his conflicts, and slid off his barstool. He was celebrating his six million joints. He couldn’t tell anyone that’s what he was doing, but it was easy to see whose load had come in, because they were handing out drugs like cigars when a baby is born. The night became a cocktail of jungle paintings, conga lines, pelican-faced crooners, and women with shimmery, minnow-shaped earrings.
Along about 3:00 a.m. was my father’s pumpkin hour, when he rented a room upstairs. He invited what girls he could and hired those he couldn’t. He heard the ding of the elevator, the click-clack of high heels on buffed marble. His room was as high as possible and facing the ocean, so no one could look in, and he and his friends could be naked for days.
Out on the balcony he let his senses fill with the creak of lazily swaying traffic lights, the smell of night-blooming jasmine. He watched the usual mayday flares streak skyward and, if he is anything like me, he followed a thought in his mind, the one we all have when it’s late and the view is of everything, the one that’s been reverberating in my brain ever since: How the hell did I get here?
Fourteen years earlier, in the winter of 1970, my father was staring out on a very different body of water. He was sleeping in an uninsulated cabin on Long Island Sound, waking only to watch the waves crisscross to nowhere and back again. Outside his door the euphoria of the Summer of Love had worn off. In the course of the past two years there had been well over a hundred politically inspired bombings, not including arson and vandalism.
The authorities responded with a violent spree of their own. They donned riot gear and whirled nightsticks. Bullets tore through clothes, pierced soft flesh, and exited slick into a sunny day. The first student died at the University of California, Berkeley, in 1969. Four more perished at Kent State a year later.
It was all too much for my father, a man who pukes when he sees puke and is so queasy around illness and human frailty that he would sooner leave the room than sign your cast. He resigned from Students for a Democratic Society, quit a graduate program at the University of Detroit, and came east to the Connecticut coast for a new adventure.
At first he shacked up with a couple of hard-drinking acquaintances, a dirty-haired married couple. They spent their hours moving full bottles of Jack Daniel’s out of one case and slipping empties into another. It was factory-like alcoholism, orderly oblivion. In my father’s considered opinion, it was uninspired behavior.
He had been an English major and a philosophy minor, and he was acutely aware of his own image, found romance in his own dissolution. He wasn’t alone in this strange endeavor. As the decade progressed, thousands of middle-class white kidsspared the bread lines and tank brigades of earlier generationsswore allegiance to their own stories, trying to shape their lives into some sort of gorgeous experience. My father did this more self-consciously than most.
He read Norman Mailer on the “enormous present” in black America. He adored Jack Kerouac’s alter ego in On the Road, a man who strolls through the magically lilac-scented slums of Denver, “feeling that the best the white world had offered was not enough ecstasy for me, not enough life, joy, kicks, darkness, music, not enough night.” He read Allen Ginsberg and felt like Howl was about him and him alone, dragging himself through Harlem streets at dawn looking for “an angry fix.”
My father had picked up a smack habit a few years earlier, memorizing the lyrics of “Heroin” by Lou Reed and the Velvet Underground. He was a contemporary of the New York author Jim Carroll, who was also a devout user in the late 1960s, and who described it as “just such a pleasure to tie up above that mainline with a woman’s silk stocking and hit the mark and watch the blood rise into the dropper like a certain desert lily I remember . . . so red . . . yeah, I shoot desert lilies in my arm.” My father began to call it “getting pinned.” As in a thousand angels on the head.
He moved into the beach cabin to soothe mind and body alike. He hoped to beat the habit, which he had tried and failed to do a few times before. Drugs are known for their destructive potential, but in the dance of starting and stopping and starting again my father found a never-ending dream of renewal, the future full of possibility, potential, the pleasure of becoming. As the basis for a life, he thought, it was as good as any.
His cabin was actually a beach bungalow on the grounds of a summer resort. He had been hired as the off-season security guard, an inspired choice by the management. My father relished the way winter attacked a basic clapboard abode on the Connecticut coast. When he got cold, he sat in his used mint-green Dodge Dart and added songs to the sound track of his life. When he tired of watching the waves, he walked to the Beachcomber, local watering hole of the counterculture.
The walls were decorated with dusty nets and plastic aquatic life. The bar was unvarnished and uncomfortable with wobbly stools and no brass footrest. But the crowd’s personal style ran toward a blend of Johnny Appleseed and Elvis. One of the regulars wore a brown coat with dangling leather fringe. My father sipped rum and coke and swayed to the Doors, scoping out the scene. Every song he heard, every conversation, seemed calibrated to give him the impression that the sadder he was, the smarter he wasbut wipe away the generational honey-glaze, and really he had reasons to feel depressed. He had no friends, no future, and a frigid, withdrawal-wracked present without end. He started looking at every woman who walked in as though she might save him. Almost unbelievably, one did.
My mother, Ann, grew up in one of the wealthier suburbs of New York City. She was born in 1950, the first of five siblings in a home of smooth surfaces and a neighborhood of the same. Her father, Louis, was an abstemious, hardworking man who played minor-league baseball for the Brooklyn Dodgers in 1943, and then joined the army and saw a bit of war. He was part of a tank brigade for a while, and his experiences yielded one or two concerned postcards, according to family lore, but the defining experience was a good job on the base driving the commander around and playing Saturday baseball games in Texas.
Back home he took over a small family grocery and liquor store, and ran the shop with the care of a founder, not an inheritor. He worked long hours and never drank from the stock or borrowed from the till. He was such a clean whistle that he even loathed his Italian heritage because it inspired so many whispered connections to the Mob. He refused Italian food, forbid his kids from speaking the language, and showed his love in the unspoken style of so many mid-century fathers. For one thing, he taught them how to drive out of a skid.
There were a few ribs in this otherwise smooth existence, however, and these ribs would make all the difference for my lonely father, waiting for help in a seaside bar. Louis was a teetotaler, but his wife, Claudia, drank. Nobody knew it at first. She bought her booze at least one town away and hid the bottles in the closet of her youngest daughter’s bedroom, the only closet no one would check. Mary had been born with a normal functioning mind, but her hips were askew and the doctors decided to operate when she was still an infant. One operation. Two operations. Each operation required an anesthetic, and the anesthetic may have curbed oxygen flow to the brain. By the time my mother was a teenager, Mary was in a wheelchair and in need of twenty-four-hour care.
When Claudia stopped vacuuming the house regularly and failed, on occasion, to fetch her children from school and activities, my mother didn’t suspect alcohol at first. Claudia was masking clear liquors with Sprite and brown liquors with ginger ale. But one day my mother found the empty bottles in Mary’s room, and she addressed the issue in the only way that made sense to her. She didn’t stage an intervention. She staged a play. She pretended things were normal. Then she staged an insurrection. She made things normal. By the time she graduated from high school in 1968, caring for others came as instinctually as driving out of a skid.
Meet the Author
Tony Dokoupil is a Senior Writer for NBC News. He holds a masters degree in American Studies from Columbia University, and lives in Brooklyn with his family.
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When I read the two previous reviews of this book I knew I had to chime in. This book is fabulous! Having grown up in Miami in the 80s, I recognized all of the backdrops that the author provides, and found his depiction of the city to be accurate. The prose is at times poetic and superbly written. This is a book for smart people.
I was so excited to read this book but foumd that it just dragged. I couldn't get through it. Big bust