The Last Pirate: A Father, His Son, and the Golden Age of Marijuana

by Dokoupil, Tony

  A few hours later all was quiet and Charlie arrived wearing a new suit from Sears, which on a man just over five feet tall put one in mind of a decorated wooden figurine. He backed into an old firehouse driveway my father and Bobby used for drops, and they put the last of $6 million in his trunk.

  “Am I sagging?” Charlie asked.

  He was sagging.

  “Shipshape,” my father said, giving Charlie the A-OK sign. As Charlie edged into traffic, my father and Bobby broke to pieces. If they were about to be busted, they figured, Charlie could get busted, too, pulled over for smuggling cash. They said their solemn goodbyes. No talking during the off-season. That was one of their rules.

  My father called a livery cab for a ride to the Gramercy Park Hotel in lower Manhattan. It was his come-down room, the place where he felt safe and protected. He’d stayed there about fifty times, often in the worst room in the building, on a middle floor with a view of an airshaft instead of the picturesque park, the last large private green space in Manhattan. It calmed him to get the oldest, shittiest room because it made him feel invisible, and that’s how he wanted to feel. On the seat next to him, he had a gadabout bag filled with $250,000.

  But his mind had yet to fully quiet down and he began to notice things. The car behind him on the bridge had a suction-cup antenna on the hood. The one in front of the hotel had two guys inside sipping coffee.

  In his room he chained the door and pulled the blinds. He slipped his bag under the bed and turned on the TV. He did cocaine for the whole first night, waiting for the fateful knock. At some point he passed out and when he awoke he noticed that his shoes had been moved and the TV now made a funny sound, a tiny whine, like the casing had been opened and loosely closed. He placed the television in the hallway like the remains of a room-service hamburger.

  Then he called my mother and begged for help, which she denied. He wanted to bury the money at Connie’s again, but Connie refused and my mother wouldn’t budge, either. He swallowed a handful of Valium and sat on his bed until the whole room filled with water and he swayed like sea grass. Surfacing, he called the front desk, ordered up eight manila envelopes and a bag of rubber bands. He stuffed each envelope with six rubber-banded stacks of money, two rows of three, $30,000 per envelope, the quarter million in loose bills transformed into boring-looking business papers.

  He showered and found his way to Kennedy Airport, the Eastern Air Lines terminal. Inside his mood lifted for the first time in seventy-two hours. Here was the Grand Central of terminals, four acres of marble and wood, encased in aqua-colored glass. Eastern was the airline of the ’70s and ’80s just as surely as Pan Am was the airline of the ’60s.

  Its pilots freelanced as flying aces in the dope air force. Its ground crews moved bricks and kilos. My father himself sold a ton of airline dope that fall, the contents of a dining truck driven right off the runway. The hard part was stifling the urge to wink at every uniformed worker. Then he was past bag check, beyond the reach of the suits, flying home, just not home to me.

  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. My father always turned.

  The Mutiny was in full fury when he arrived with his friend, the coke dealer with the pencil-thin mustache. Valets and bellhops scanned the balconies, poised to dodge a falling body or lick a shimmering cloud of falling cocaine. For about $100 a year people got gold membership cards, each one numbered and emblazoned with a pirate head. The real pirates just slipped in through the pool entrance.

  As my father found his barstool, my mother was probably still wondering if he would make it home for Saturday Night Live. By the time he slid off the stool, he had forgotten the feds and the fuckups and was thinking only about his successful sale, his six million joints.

  Every room at the Mutiny had a Jacuzzi and a balcony view of Sailboat Bay, a corner of Biscayne that bristled with beautiful boats. My father rented the highest room possible, ocean-facing so no one could look in, and called his friends at the escort service, placing his order with the precision of a chef’s grocery list. Out on the balcony he watched the sun bounce up behind the horizon and he followed a thought in his mind, the one we all have when it’s late and the view is of everything.

  Then he stopped thinking entirely.

  Later that winter, after my father’s long, slow descent had begun but before he knew it, he took me to Disney World, where we celebrated my fourth birthday and generally went bonkers all over the park. The most memorable part of the trip wasn’t a ride or a character, however; it was the hotel room. My father left me in it. He did it one night, two nights. His plan was working fine—father by day, barhopper in Orlando by night—until my mother called, patched through by an operator directly to her son.

  It reminds me that there are really two versions of my family’s story, as there are two versions of every family story. There’s the good one—dopey, smiley, basically a lark—and there’s the bad one, which is everything that happened in between the good times, filling the gaps and threatening to transform our irregular but essentially happy lives into a tearjerker in the tropics. My father was funny and charming but also frightening and self-destructive. It’s impossible to pinpoint exactly when his personality flipped, but it did, and it flipped the story of my family with it.

  II

  Exhale

  5

  Three Little Blond Boys

  New York City, 1898–1970

  My father was born in New York City in 1946, the second of four siblings. One day, many years later, when my father was all grown up, he began a journal and recalled his childhood this way: “I was traumatized many times over … I can almost feel the dozens of times that I was brought to crying … I felt no love or nurturing or happiness or joy … I lived in a grossly abnormal and dysfunctional home. ‘Home’ is not even an accurate term for the apartment we lived in … I never had a chance.”

  These aren’t even his memories.

  In his journal, it’s all labeled “pre-memory”—as in before the age of five. And yet there were other working-class Catholic boys with circumstances like his who didn’t become schedule I narcotics dealers. His two brothers, for example. David, the eldest, went on to an aeronautical engineering degree at Berkeley, a long marriage, two children, and a fine career with a leading maker of archival equipment for libraries. Joseph, who came after Anthony, humped it as a foot soldier in Vietnam, came home, married his high-school sweetheart, had kids, and kept on humping it as a mail carrier for the U.S. Postal Service.

  To make sense of Anthony—to understand how he came to the low life and came to love it, along with many other seemingly blessed young men of his era—it’s necessary to go back a ways, to reconstruct what he insists is “the pattern of our life.” My father was one of three little blond boys. His father, Henry, was one of three little blond boys. His father’s father, Paul, was one of three little blond boys, the first of our line of Dokoupils to come to America from what was a Czech-speaking part of Austria. My father says every generation had a demonic Dokoupil patriarch, a man who withheld love and affection and warped his children’s lives. Ergo, Great-grandpa Paul “never had a chance,” and Grandpa Henry “never had a chance,” and Anthony himself “never had a chance,” which of course means I “never had a chance” and neither will my son, little blond boys both.

  My father was still a stranger to me when he explained this family pattern, but I felt the pull of his logic immediately. We tell children they can be anything they set their minds to, pretending it does not matter where those minds came from. But there’s no escaping the calculus of family. The math has to work and that’s what scares me.

  The first Dokoupil to come to New York City was John Joseph Dokoupil, a Czech laborer who arriv
ed in the late 1890s with his wife, Rosa. Both were in their early twenties. They settled on East Fourth Street in what’s now Alphabet City, and John got a job at the PowerHouse, an electric generator about ten blocks north on the East River. Three boys followed in quick succession: Anthony in 1896, James in 1897, and Paul in 1898.

  My father remembers his great-uncle Anthony—his namesake and by extension my own—as a charming, blue-eyed man with a firm dislike for traditional work. According to legend, his father, John, got this first American Anthony Dokoupil a job at the PowerHouse, which he quietly resold to another man, who worked the job as Anthony but earned only a fraction of the wages. Anthony pocketed the difference, and this allowed him to work as a gambler and bookie and eventually as an illegal gin maker and runner of Canadian whiskey during Prohibition. Or maybe he worked as a loan shark. No one seems to know for sure. My great-aunt Jean, who married Henry’s brother Jack and is the oldest living relative I have, talks about this ancestral Anthony as a “muckety-muck, a big shot, a wheeler-dealer, a gambler. He always had bucks. He was really good.”

  “But what did he do?” I asked.

  “He was a shrewdy,” Jean said. “I don’t know.”

  Whatever it was, it made him rich. It got him out of the city and into an estate in Westchester. The shrewdy’s younger brother, Charles, is said to have died of an opium overdose in his twenties and left not a trace, not even a memory of a memory in the minds of those living today. All of which leaves Paul, my great-grandfather: the youngest brother of a criminal and a drug addict. You might think he could do no worse, but he did; he became an unmarried teenage father. According to the Catholic Church, which confirmed the birth with an elaborate placard, a boy named Henry was born on Christmas eve in 1915, which, as spooky, unsubtle fate would have it, is the same day I was born sixty-five years later. His parents, Paul and Geraldine, were seventeen years old. According to the City of New York, they were married when they were eighteen years old.

  And what followed is an old story of dashed dreams, soured lives, and the unwanted son who rages forward into a new generation. Paul got a service job at another power plant in the East Seventies and moved his young family to the neighborhood, renting a second-floor railroad apartment with a potbellied stove he liked to lean against in the winter, a cup of Fleischmann’s rye whiskey in his hand. In the summers, it was beer and a breeze by the street-side windows.

  In every season, it was common for him to get knee-walking drunk, and for Geraldine, a riotous Italian girl, to call him a drunken bastard. The only thing these third-generation Americans could say in Czech was “beer” and “money for beer.” Paul kept a keg next to the kitchen sink, when he could afford it. The Paul Dokoupil household did have a dog. Its name was Combat. Its purpose was to help Paul home from the bar.

  Two more boys followed Henry in quick succession. Jack was the favorite son and James was the mama’s boy. Henry was sort of the whipping boy. He took the blame for things to protect his siblings, but he also caught fury simply for being alive. It was Henry, after all, who had gotten Paul into this mess of domesticity and for that Paul whipped him badly with a belt buckle, flecking off patches of skin. Decades later, people said Henry’s back looked like a moonscape.

  When the Depression hit, Paul made his great mistake of a son quit school—where the boy was apparently an honor student—and get a job. Henry consented and by 1935 he was working at a box factory while his two younger brothers were high-school graduates. He worked two years at Densen and Banner Corrugated Box Company, answering phones and filling orders, then climbed into a sales job with Acme Box of New York City, where he managed old accounts and brought in new ones, previewing the basic nature of his offspring’s knack for the pot business.

  Then the war came. James, the middle child, joined the marines, took German machine-gun fire during the Battle of the Bulge, and came home to become an accountant and commander of his local VFW. Jack joined the army, defended the Pacific Islands, and remained in the service for another three decades. Both men married and are remembered by their children as quiet, loving fathers. They drove the station wagon, worked the grill.

  Henry also joined the armed forces. He enlisted in the Army Air Corps in 1939, when he was twenty-one years old and still unbreakable. He was good-looking. People used to say he was built like Aldo Ray, the tough-guy star of What Did You Do in the War, Daddy? and The Naked and the Dead. Even my father was impressed, once telling me, “He was an Adonis, Tony, an absolute Adonis.” And actually, he rather was. Pictures of my grandfather confirm an Easter Island–like gravitas, a face that is all shadows and planes until it’s lit by the kind of smile that helped him sell commercial paper products by the ton.

  In May 1941, in a falling-down church on East Seventy-ninth Street, where the convent hadn’t been painted in twenty-five years, Henry married Phyllis, a pretty Italian girl he had known since childhood. Phyllis dreamed of being a designer and was known to work magic with a sewing machine. If you needed a hat for an important occasion, Phyllis was your gal.

  But just weeks after their wedding, Phyllis was pregnant and Henry was gone, transferred to a new Army Air Corps base at Manchester Air Field in New Hampshire. The first squadron of A-20 attack aircraft arrived on Saturday, December 6, of that year, during a family-friendly weekend that also brought Phyllis up for a visit. The following morning, after breakfast together, she and Henry joined dozens of other cozy young couples for a midday movie but suddenly there was no movie. The screen flashed white, and as the projector clicked pointlessly somewhere above them, an officer said what hundreds of officers and air sirens and ringing phones were saying coast to coast at that very moment: “WE ARE UNDER ATTACK.”

  Phyllis pushed through the throng and, uncertain where to go or what, if anything, would be attacked next, she got on a train back to New York City and into a cab at Grand Central. Maybe something happened to her in the crush exiting the theater, or perhaps the news itself had been enough to upset her equilibrium. In any case, she had enough time to say “Take me to the hospital” but not enough time to get there: She had her baby right there in the back of the cab.

  It was as perfectly shaped as the model in her doctor’s office. But it never cried, and she only held it once before the hospital took it away and produced a form for her to sign. There was no possibility of a funeral, no grief counseling in those days. An orderly pointed to a grimy phone that could be used to call for a ride. Phyllis was decades older, a grandmother, before she could talk openly about the loss. And in the intervening years she always hesitated when asked how many children she had. Was it four? Or should she say five? Henry never said anything at all, certainly not while the war was going on, which was a period that lasted more or less the rest of his life.

  His character changed after Phyllis lost the baby. His aspirations seemed to drift. The army saw him as a machinist, a uniformed mechanic who banged out the dents in planes and made their engines hum. But he pushed back against those expectations, asking to be relocated to Miami and put into the planes themselves, where he most likely toured the gin-clear waters of the Caribbean, tracing the same path his son would in the decades to come, albeit as a man concerned with bombers not bales of marijuana.

  Henry must have felt like a real soldier, whatever he was doing, because Miami mattered at that moment in the war. German and Italian U-boats were attacking Allied tankers and oil refineries, sinking ships and taking lives. He was promoted to corporal, then again to sergeant, and again through two levels of seniority and into a mentoring role for junior officers.

  At last, on February 10, 1944, he left the tropics, taking the Queen Elizabeth from New York to England, to the airfields on the North Sea. He became part of the 702nd Bomb Squadron. The big boys. The B-24 heavy bombers. The Wings of War. He joined the crew of a plane called Bodacious, and he took flight with much the same spirit that would later send his son into a bodacious professional life of his own. From the day he got his transfer papers
Henry felt like a man in the movies.

  His week at sea marked the start of the most intense Allied bombing of the war: the three months before D-Day, the deepest, most sustained assaults on Germany. The flight path of the 702nd was known as “flak alley,” where the antiaircraft bullets came in great undulating streams, black from guns on the ground, orange and green tracers from the German interceptors. The bombers were always losing pieces of wings, rudders, windshields, propellers, landing gear.

  Whatever came, Henry’s job was to keep the bird’s feathers on and the beak working, and when German fighters were thick in the air around them, he fired a machine gun, too. He was an engineer-gunner, the most mobile member of a bombing crew, bouncing from the top turret to the ball turret, to the bomb bay, and even below it to an exterior catwalk, miles above the earth. If the shells got stuck or the doors froze shut, his job was to drop the bombs manually, and if the pilots were killed, he was responsible for cranking down the landing gear and flying the plane home.

  The average lifespan of a B-24 was twenty missions. After Bodacious survived twenty missions, the army added five more, and then five more, and five more. In six months, Henry logged more than two hundred hours of combat air time, and Bodacious bombed thirty-three cities; Henry stenciled each onto his bomber jacket in black marker. He won three Oak Leaf Clusters, a Distinguished Flying Cross, and an Air Medal for his efforts. Each citation pushes some version of the phrase “cool under pressure,” which is another trait he surely passed on to his son the drug dealer.

  A picture of Henry taken overseas shows a happy young officer riding a bicycle in the English countryside. But something happened in August 1944 on the thirty-fourth mission. Henry’s complete military records were destroyed in the St. Louis archive fire of 1973; the only remaining army paperwork, besides what he kept, is his final pay stub, which records his discharge from the Army Air Corps’ mental hospital in St. Petersburg, Florida. The other nine men on Bodacious are still on mission thirty-four.