My Father The Dope 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. (Article continued below...)

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.