My Father the Drug Dealer

I loved the car trips I took with my mom as a kid. In 1986, we climbed into a rented motor home and bolted south Florida for the mesas of New Mexico, seeing cousins and digging for Indian arrowheads in my aunt's yard. Later we toured New England, New York, and the Southeast, my mom taking advantage of the long hours behind the wheel to grill me about my grade-school crushes and playground fights. I thought we were just bonding and visiting family. Years later, I would learn that the trips had another aim: to hunt down cash and valuables my dad had stashed during his days as one of the biggest suppliers of high-quality marijuana in the Northeast.

The richest prize was a half-million dollars stuffed into a Styrofoam cooler and hidden in a hillside near my cousin's house. We hit Florida's Redland region to pick up a pair of collectible cars (Mom wound up loaning them to the makers of Miami Vice). We went to Long Island to look for a few more coolers packed with cash. Sure, Mom loved the open road. But she also knew you couldn't take more than $10,000 on an airplane without telling authorities.

From 1975 to 1986, Anthony Edward Dokoupil distributed at least 50 tons of Colombian and Mexican grass north of the Mason-Dixon line. He started small, with suitcases and a rental car that he would drive up from Florida. As he cultivated his Latin American connections, he graduated to his own Buick with a trunk the size of a Jacuzzi and specially equipped air shocks that kept the car riding high despite a several-hundred-pound cargo of "Dade County pine." Later my dad bought a hardtop Chevy pickup with a three-quarter-ton capacity, and hired three others to drive convoy-style up I-95, or what he called the "Reefer Express." By the early 1980s, he and a partner were ferrying weed around New York in garbage trucks and a refrigerated rig marked mario's fish. At his peak in 1986, my father led a team that smuggled some 17 tons of Colombian pot on sailboats from the Caribbean—enough to get every college kid in America stoned. He says he raked in around $2.5 million altogether—or $6 million in today's money. As Jimmy Buffett sang at the time, "I made enough money to buy Miami, but I pissed it away so fast." My father liked the tune; unfortunately for my mother and me, he lived it, too.

I wish I could say that Anthony was an unlikely criminal, but that's not so. His namesake, his great-uncle Anthony, was an alcoholic who made a small fortune smuggling Canadian whisky during Prohibition. My father is a 62-year-old pensioner who still uses crack occasionally, a man who blew his riches on hookers and hotel rooms, hit my mother, slept under bridges, and bottomed out so completely that he was actually grateful when the U.S. marshals finally came calling. I, for the record, am not an Anthony—either on my birth certificate or so far in life. My father's implosion has been too complete for me to really fear becoming him. I have a lovely wife, good health, great friends, and a job I like, so it's hard for me to imagine detouring into a life of drugs and crime. But he still haunts me, making me fearful of the genes I carry and the man I may become.

My father has shaped my life in absentia. Because I knew he did drugs, I didn't. Because I had no good male role model, I searched for them elsewhere, reporting out stories about men's behavior—as though journalistic research could fill in for the father who wasn't there. Recently, that search has taken on greater urgency. Late last week I became a father for the first time; we had a boy. While most dads look forward to passing along the family heritage, I'm keen to effectively replant the family tree—to recast what it means to be a man in the Dokoupil clan. To do that, I knew I needed to go see my father—something I had done only once before in the past 20 years.

On a drizzly day in late June, I took a train up to Boston to meet him. I recognized him, standing at the end of the platform with the same trim mustache he's had since I was a kid. I sized him up: beige windbreaker, jeans, slicked-back hair. With red-rimmed eyes and ashen cheeks, he looked like a man from a public-service announcement about liver disease. "God, you look like a movie star," he said, and compared with him I suppose I did. In the dead silence of the car-rental shop, I could hear his breathing, quick and shallow. We drove to his government-subsidized apartment near Harvard University—a spare and grimy place, adorned with Christian iconography, two cigarette-scarred plastic cups, and a liter of Diet Pepsi in the fridge. He told me he doesn't have a steady job and that the free lunch from a local senior center is his main source of food.

For the first 10 years of my life, Big Tony—as my family called him—was someone I adored. He taught me how to hit a baseball, read a newspaper, and "shave" (without the blade). But by the time I needed a shave and cared about what was in the paper, he was long gone. Of course, that's not what he wanted to focus on as we sat at the card table in the center of the room. He said he was happy about the apartment and he bragged about his health: "My lungs are great, Tony—you're so lucky, you're going to live forever." He also said he was proud of his parenting skills. "I was a good father. I took you everyplace. I bought you everything," he said through drags on his Liggett Selects. "I was always with you … when I was home." But he broke down when I asked him where he had gone. "I abandoned you," he said, his eyes welling up. "I never came home. I harbored so much guilt over that, I felt like I could just lie down and die." And I believed him, at least a little bit.

Big Tony was born in 1946, the second of four siblings. He was raised in a comfortable Roman Catholic enclave of northern New Jersey. Christian Brothers guided him toward God and taught him in high school, even as he spent weekends in Manhattan, looking for trouble. He tried heroin as an 18-year-old in the summer of 1964, after earning admission to Loyola University in Los Angeles. He continued using drugs during his freshman year, and soon transferred back home to St. Peter's College, where he graduated with an English degree in 1968. That fall he enrolled in a philosophy master's program at the University of Detroit, where he joined the antiwar group Students for a Democratic Society and fell in love with Kantian ethics.

By 1970, however, morality and my father had begun to definitively part ways. He dropped out of school and shacked up with a pair of hard-drinking buddies in Milford, Conn., a beach town about 10 miles outside of New Haven. Usually flying on coke or heroin, he spent his nights at the Beachcomber, a college bar where he'd drink rum and Coke and sway to the Velvet Underground. He'd also scope out the crowd, which on one night happened to include my mother, Ann, a Southern Connecticut State University student. Dressed in a long red coat, she reminded Anthony of a Russian doll, albeit one with a mood ring. My mother liked his Kant-quoting ways, blue eyes, and sleepy smile. The year after she met my father at the Beachcomber, a career-placement test noted her "superior" judgment, an abundance of "common sense, foresight, and the ability to reach sound decisions." And yet she went home with my dad that night, and stayed with him for 15 years. "He smiled a lot," my mother recalls. "I didn't realize until later that he really didn't know what smiling was all about—what happiness was all about."

Then again, my mother had always been the caring type. The oldest of five children, she grew up in Cross River, N.Y., working in the family-owned grocery store, helping to raise her brain-damaged younger sister, and trying as a college freshman to steady the family when her father left home and her mother's drinking habits came out of the closet. By the time she met my father, looking out for others was second nature—as was reaching for a joint to help her relax. She knew my father had addictive tendencies; "we all did. It was the '70s," she says.

They lived in a rambling beachfront house with three roommates, and spent my mother's last two college years blissed out on pot, hash, and pills. Party bowls brimmed with Valium, Seconals, and Black Beauties, and speakers blasted the Stones, the Dead, and Janis Joplin. The group started selling hash to fund the good times. "We were flower children, we helped each other out, we made each other food, and we sold a little pot to our friends," remembers one of the roommates, Karen, who like others in this article asked that her full name not be published because she doesn't want people to know about her past drug involvement.

Most saw the drug trade as a way to make a little spending money. My father saw it as a serious business. He had a point. In the mid-1970s, demand was on the rise, and most of the stuff was imported, creating the need for a distribution chain. The law often looked the other way. The 1972 National Commission on Marihuana and Drug Use had unanimously recommended decriminalization. It was "The Great Stoned Age," in the words of author and drug aficionado Martin Torgoff. "[Dealing] made you a hip, happening fellow," says Keith Stroup, who founded the National Organization for the Reform of Marijuana Laws in 1970. "I wanted to be a big shot," says my father, whose illegal activities I reconstructed based on federal records and interviews with him, my mother, three of my father's former partners (including my stepfather), Dad's onetime lawyer, and two close family friends.

The money was good. After graduating in 1972, my mother earned around $10,000 a year as a teacher, and my father wallowed in a dead-end job making concrete steps. They wanted to get their own place, so sometime in 1974 my mother took out a $2,000 loan from her father and gave it to Anthony to buy some "Mexican bricks"—slang for kilos—from a pair of local distributors. "I sold it lickety-split," my father says, "but people kept asking me for Colombian," which was supposedly free of the lung-killing pesticides that Uncle Sam had started spraying on vast tracts of Mexican land.

Tapping a distant family connection, Tony got a new gig in 1976: running Winnebagos full of Colombian weed from an entry point in the Florida Keys to the parking lot of a major Miami mall, where he'd leave the keys on a back tire for the next driver to find. The ride up a single-lane road swarming with local law-enforcement agents was a reputation maker for my father, who soon found himself managing his own team of wheelmen. Suddenly he was making six figures a year, enough to buy a new house for my mother, who not only knew where the money was coming from but also fundamentally believed in the business. "I thought pot was an acceptable choice that should be legalized and used for medical relief," she says.

My father thought pot should be used for a lot of other things. He replaced his hippie garb with Miami Vice cool—white pants, mesh shirts, a Rolex, a coral ring, and an inky-blue Mercedes sedan—and rented penthouse suites on Biscayne Bay and in downtown Miami, where the cocaine came in softball-size mounds and the prostitutes sometimes stayed for days. "It was a f---ing thrill," he says. "I never wanted to stop." And sometimes he didn't, bringing a hooker to a New England party full of family friends—an episode that ended with my mother locking him out of the house for a spell. There were also weeklong benders through the Caribbean, where in 1978 my father started working with a more versatile ring of East Coast smugglers.

The timing was fortuitous. Eleven states had reduced the penalty for pot possession, making it tantamount to receiving a parking ticket, while 30 others had eliminated jail for first-time offenders. Even President Jimmy Carter had endorsed decriminalization. Anthony's new contacts—Willie, Ray, and Steve—introduced him to the world of 10-ton loads and million-dollar payoffs. Willie—who according to my father and other smugglers in the ring has assumed a different identity under the witness-protection program and couldn't be located for this article—ran the shipping side of things, getting an old tanker full of weed from Colombia to the Caribbean islands. From there the load was parceled out to private sailboats, some of which belonged to unwitting East Coasters who paid to have their yachts moved north for the season. Timed to blend in with regatta traffic, the sailboats would head to summer spots: the Chesapeake Bay, Cape Cod, the Hamptons, and other points as far north as Maine. Ray, a carpenter and former college wrestler, helped organized the pickups, using inflatable rafts to ferry the stuff to land. Steve and Big Tony handled distribution, renting safe houses to store the loads and carve them up for local dealers. Once, they paid my mother's friend Karen $1,000 to get lost so they could use her house on Long Island. "I came home and your father had counted out a million dollars in the living room, right where we all sit for Thanksgiving," she recalls. "That was a trip."

Flush with cash, my parents moved to Miami in 1981, a few months after I was born. My mother quit her job, and, with the help of a crooked accountant, my father set up a pair of housing companies to help him launder the drug money. There was another Mercedes, a 35-foot cruising yacht in Biscayne Bay, and frequent Caribbean vacations. I was enrolled in the prestigious Gulliver Prep school, where my classmates included President George H.W. Bush's grandkids. And I was clueless as to my father's chosen profession.

The high life continued for almost a decade, but the political tide was beginning to turn. During the 1980 presidential campaign, Ronald Reagan branded marijuana "probably the most dangerous drug in America." As president, he boosted funding for the fight against smugglers tenfold to $205 million and backed a series of new laws allowing for unprecedented crackdowns. Officials seized hotels, ranches, planes, boats, and topless bars. In an effort to halt what The New York Times called the "annual invasion" of weed every summer, the Coast Guard started firing on ships that failed to respond to radio contact, and racking up busts, according to press reports from the early 1980s: 28 tons on a cargo ship off the Massachusetts coast, 32 tons on a shrimp boat near the Florida Keys, 70 tons on a freighter at the mouth of the Mississippi.

In 1983, the gang planned one more deal before getting out of the game. And they pulled it off: an 11-ton shipment that netted my father a half-million dollars (the money ended up in that New Mexico cooler we went searching for years later). What followed wasn't your average office retirement party: a weeklong bacchanalia on a 65-foot schooner near St. Bart's. My mom, my father, and I were all there, along with other smugglers, distributors, dealers, and their families. Everybody seemed to be having a good time, except my dad—who by this point had broken the cardinal rule of dealing and become a full-blown coke and heroin addict. He left the party in search of both.

The business proved harder to exit. In 1986, my dad banded together with just about the only people in town still willing to take a risk with an increasingly unreliable druggie. The new crew had names straight out of pirate central casting: Jimbo, Corky, Inga, Timber Tom, and Scrimshaw Mike, along with four other lackeys and Dad's old partner Steve. The team hauled 17 and a half tons of reefer into Urbanna, Va., a tiny oyster port on the Chesapeake Bay. It was my father's biggest payday: three quarters of a million dollars, more than enough, he hoped, to get his life back on track.

Instead, he skidded permanently off course, losing most of the money in an off-the-books investment in a Yukon gold mine, and sending the rest up his nose or into his veins. "I don't even know where it went," he says today. "I was totally fried."

Between 1987 and 1989, my mother paid for him to enter several high-end rehab facilities in the South. She would take me to see him, dropping me off to go fishing or walk the grounds as she sat in the car listening to oldies and digging into Tupperware bowls of homemade pasta. "I must have gained 40 pounds in the late 1980s," she says. "It numbed my pain." She also started pouring money into her own emotional rehab: she visited a therapist weekly, earned a University of Miami certificate in chemical dependency and drug counseling, and attended touchy-feely conferences with themes like "Healing Yourself" and "Self-Nurturing."

Clueless about the smuggling, I handled the rehab years by swallowing my feelings. I was embarrassed for my father, whose outreach consisted mostly of cringe-inducing letters and creepy rehab art he sent me from various institutions. One such offering: a life-size cutout of his body with outstretched arms emblazoned with the words "I love you this much." Although I was 8 years old, he alternately treated me like a toddler and a grown man. On my ninth birthday, he skipped my party but dumped a load of Tonka Trucks near the mailbox that were better suited to a 4-year-old. I felt I had to play with them or I would hurt his fatherly pride. For my 10th birthday, he sent me a letter in which he tenderly recalled my birth, including the moment that I "crowned." He signed it "Daddy," with a P.S.: "I don't have money right now, but let's just say I owe you one."

His attempts to get clean all failed. By 1988, he had dug up and squandered his stashes in Long Island and was living in a lifeguard stand on Miami Beach, bathing in the ocean and popping in on my mother, asking for money he said he'd hidden in and around the house. When she couldn't produce it, he'd smack her around. (Mom and I eventually found $10,000 behind the couch, and $12,000 under the washing machine.) Meanwhile, my mother started over—if marrying Ray, one of my father's drug partners and another addict (this time alcohol), counts as a fresh beginning. Ray may not have been a knight in shining armor, but he was at least familiar, someone to whom she didn't have to explain herself or her past. They married in 1989, when I was 9. I was the best man.

Soon the New England Drug Task Force began knocking down doors. Willie was busted in Portugal in 1990, and promptly rolled on the whole crew. My stepfather corroborated Willie's story in a three-day meeting with DEA agents in Ft. Lauderdale the following year. In July 1992, exactly nine months later, the Feds busted my father on Miami Beach, where he was working as part of a trash-spearing sanitation crew. The charge: two counts of conspiracy to import and distribute 35,000 pounds of marijuana in 1986—his last job. According to court documents, the Feds seized a marina in Urbanna, a restaurant in Maine, two houses in Massachusetts, and a couple of million dollars in recoverable cash from my father's crew. He spent nine months in the clink before being sentenced to time served, six months' mandatory rehab in a federal hospital, and three years' probation. 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—which would have meant a minimum of 10 years. Ray got amnesty for his cooperation. "If it wasn't him, it would have been me," Ray told me recently over the dinner table, amid sips of wine. My mother's best friend, Karen, puts it less charitably: "Ray wimped out." And yet Ray's conscience is clear. He blames Willie for flipping on people, and my mother agrees. My father hates Ray.

After Ray heard about Willie's arrest, we beat it to Maryland, telling as few people as possible. My mother swears she was hiding from my father's fists, rather than the enemies who would pile up after Ray helped rat out the ring. She taught high school (including anti-drug classes at night), and my stepfather hauled construction trash. My mother had long since retrieved the cooler from New Mexico, although she says half of its contents were missing and much of the rest went toward paying Dad's medical bills. My father also beat her to the coolers in Long Island. The cars, and some shady investment in Miami property, were lost in Hurricane Andrew in 1992. The Yukon gold mine never did yield its treasure.

I learned to live a lower-middle-class life now that the cash, fancy school, and ritzy vacations were all gone. My new public-school friends called me "poor boy," the kid who often didn't have enough money for lunch and had an AWOL father whose name my mother seldom mentioned. Maybe she was trying to protect me, or maybe she was just too embarrassed. "I feel so much shame for putting up with that stuff for so long," she says, referring to my father's boorish behavior. But she says she does not regret her choices, and is happy with the way her life and her son have turned out. Too hurt or scared to find out what had happened to him, I pictured my dad as a larger-than-life kingpin, living it up somewhere in South America. Either that, I figured, or he was dead.

In 2001, when I was a 20-year-old college student in Washington, D.C., I learned the truth when a family member sent me my father's phone number. I called, and found out that Big Tony was a washed-up ex-con, afraid of crowds and taking pills the size of pen caps to stave off drug-induced schizophrenic episodes. He didn't recognize me when I went to visit him two years ago—our first meeting since I was 9. "Your name is Tony, too? Stop s--tting me," he said when I approached him in the lobby of his building. Since then, he has occasionally sent me rambling, fantastical letters alleging that my mother is following him (she isn't) and that the radio is broadcasting his life (it's not). During a rare phone conversation about a year and a half ago he tried to sell me his computer; the time before that, his shoes.

On my most recent trip a few weeks back, he said he had less than $5 in his pocket—so I bought him a pack of cigarettes and took him out to a decent fish dinner near Harvard's campus. We made for an odd pair, I guess, because when we stopped at a bank to use the ATM, the guard came over to me to make sure I wasn't being bothered. At the restaurant Dad slipped right back into the good life, ordering a strawberry daiquiri (the restaurant couldn't make one), white wine, a plate of mussels, and coffee with a splash of Sambuca for dessert. "When you're rich you can do anything," he said with a wink. Reality returned the next morning with breakfast at a Dunkin' Donuts. My dad seemed to know most of the down-and-outers who wiled away their hours in the brightly lit space. I sized my father up again. His taste buds are so fried from drugs that he dumps 10 packs of Sweet'n Low into his coffee. His arms are shredded from needles. With dirty nails and a face banged up by prison fights and repeated falls after blackouts, he's the guy you move away from when he sits next to you on the subway. He's the guy I want to move away from now. But of course, it's not so easy.

The truth is that I've often cast myself in relation to my father, even recognizing him as a kindred spirit whose story, if I'm being honest, I've sometimes traded on for personal gain: to impress college coeds, admissions officers, professors, and even prospective employers with what I've had to overcome. His story has also given me a strong sense of direction, and an interest in sifting through truth and all its shades of gray.

Then again, I'm also ashamed of my colorful past, and angry that a comfortable life slipped from my fingers. As an adult, I've tried to erase the darker aspects of my double helix. I've married a woman far classier than myself, and with a little luck, my son will get all the things I lost too soon: the nice house, the exotic vacations, the great school, a decent dad with a moral compass. When he gets older, I'll tell him about his grandfather, although I doubt they will ever meet. When I told Big Tony that he would soon have a grandson, he was of course overjoyed. Were we thinking of calling him Anthony, he asked. "No, Dad," I said. "I don't think so."