“The Last Pirate”: My dad, the pot smuggler

A writer investigates his father's outlaw life during the Golden Age of marijuana runners

Topics: Books, What to Read, Editor's Picks, Must-Do, Nonfiction, Memoirs, Drugs, War on Drugs, marijuana, The Last Pirate

“If you smoked Colombian weed in the 1970s and 1980s,” writes Tony Dokoupil in his new book, “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 grandkids, at least for a little while.” That “little while” matters, because Dokoupil, whose father smuggled tens of thousands of tons of marijuana into the United States during those decades, would, by the 1990s, be living a hand-to-mouth existence just one step above a trailer park with his mother.

“The Last Pirate: A Father, His Son and the Golden Age of Marijuana” is a book with a double identity and a double conscience. The major part of it recounts Dokoupil’s father’s adult life, a rakish saga of small planes, sailboats and RVs loaded with contraband worming their way past authorities whose commitment to cutting off the flow of pot from Latin America fluctuated almost as dramatically as the Dokoupil family finances. The book is fascinating, as procedurals often are, and highlights a few truly ingenious gambits, such as arranging the influx of small, marijuana-laden watercraft into New York Harbor to coincide with the national bicentennial celebration known as the Parade of Ships; the smugglers went unnoticed among the tourist boats that turned out to welcome a fleet of antique schooners, brigantines, brigs and barques.

On the other hand, a lot of the so-called action in this line of work involved sitting around in bars for hours with mustached guys, juggling the fistfuls of quarters that pot “pirates” spent on the pay phones they used to checked in on various stages of a deal. Whether you find any of this “romantic” (a favorite word of the author’s) or not is largely a matter of taste and disposition. Dokoupil’s father did, and “The Last Pirate” at times reads like the son’s ambivalent tribute to the way of life for which he and his mother were abandoned. He assures his readers that for his father and his cohort, this lifestyle was “never about the money,” a claim likely to send eyebrows skyward. But Dokoupil makes his case. His father squandered, gave away, allowed himself to be robbed of and in many cases just plain lost hundreds of thousands of dollars as easily as he misplaced his family. What he was really in it for was the risk and the thrills.

The pot Americans smoke today is almost entirely homegrown, sleekly and cleanly bred and raised. By contrast, “my father’s pot was dirty: doused in ocean spray, soaked in fuel, infested with spiders.” But for decades, the heyday of Dokoupil’s father and his cronies, smuggled dope was the only — or at least the best — game in town. Dokoupil offers a history of the American marijuana trade during those years, when smugglers were celebrated as daring counterculture heroes by magazines like High Times, men and women who put their freedom and occasionally their lives at risk to help their fellow freaks get high. Well, and also to make a buck — lots and lots of bucks. For a while, during the Carter administration, decriminalization advanced and legalization seemed imminent, but then Ronald Reagan and his gaunt, piously anti-drug wife took the White House and turned up the heat again with their war on drugs.

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In counterpoint to this story of pot smugglers as dashing pirates (a term Dokoupil’s own father used), there’s the more intimate tale of the younger Dokoupil and his mother, Ann. As the mothers often are in sons’ memoirs of their father, Ann is a mysterious and complex figure. She was woman who knew what her husband was up to and supported much of it, even helping out with an operation on occasion, but who realized at a certain point that she needed to start beefing up her teaching résumé and burying cash. Dokoupil’s father would disappear for days or weeks at a time, and he spent much of the fortune he earned on cocaine and prostituted women. At times his temper grew violent at home. But Ann’s son got a top-notch education and they lived in a series of luxurious homes until the day she put her escape plan in motion.

When Dokoupil, a high school baseball star turned P.R. whiz, finally reconnected with his dad, the older man was an ex-con (after serving a notably brief prison sentence) and diagnosed schizophrenic who had slept for a while in a box under a Floridian bridge. The son had a son of his own, and “The Last Pirate” is haunted by what Dokoupil perceives as a stubborn paternal legacy of danger-seeking, poor impulse control and irresponsibility. Can this heritage be jettisoned? Does Dokoupil really want it to be? In the book’s most memorable chapters, Dokoupil describes his adolescent years, when he bragged to his friends about his big-time drug dealer dad. He knew next to nothing about the man he’d last seen at age 6, but “I feathered those bones until I had a father I could live with.” The half-broken father who got in touch with him later, sending loving but sometimes crazy letters, only threatened this useful myth.

That’s where the double conscience of “The Last Pirate” comes in, and makes Dokoupil’s biography cum memoir more than just a rollicking, dope-saturated yarn. Yet the book is also a rollicking, dope-saturated yarn; there are sentences describing the elder Dokoupil’s operations where every swash is so extravagantly buckled that you can barely makes sense of the story for all the hardware it sports. Presumably this Vice-ified prose style is in some part a concession to the sort of blunt-witted audience likely to be attracted to a book about a big-time dope smuggler. Yet bullshitting is a Dokoupil family tradition, too; it’s what both father and son do when they invoke Blackbeard and bootleggers and generally churn out great frothy masses of mystique in which to swath what might otherwise look like a fairly sordid tale of untrammeled self-indulgence.

For, if Dokoupil’s father didn’t abandon his family to pursue a pirate’s life, a life bewitchingly, irresistibly “romantic,” then what did he leave them for? This is the agonizing question that the latter portions of “The Last Pirate” circles around, until the crucial moment when Dokoupil finally confronts his father to ask where the time and money and love went — where the man himself went and why. And of course, he ends up having to answer it himself, “You had to piss it all away or you wouldn’t be an outlaw.”

Laura Miller
Laura Miller is a senior writer for Salon. She is the author of "The Magician's Book: A Skeptic's Adventures in Narnia" and has a Web site, magiciansbook.com.

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