With an antiheroic father leading a dual life and family values juxtaposed with the criminal’s code, The Last Pirate unfolds like a literary cousin of such shows as The Americans, The Sopranos and Breaking Bad. In fact, a Breaking Bad connection smacks the reader in the face on the first page, when the author, Tony Dokoupil, flashes back to a 1988 night in Albuquerque, where his mother repeatedly dug into the soil outside a cousin’s home in search of a Styrofoam cooler. That cooler had been buried there by her husband. And it contained $500,000 in stacked-and-bagged cash.
If Dokoupil’s dad, Anthony — Big Tony to his son’s Little — is the Walter White in this scenario, that makes the writer of this fine work of nonfiction a Walt Jr. of sorts: the son left to wonder why his daddy loved trafficking in illegal substances more than he loved his own boy.
Anthony Dokoupil, one of only four characters in The Last Pirate whose names haven’t been changed to protect the non-innocent, is a more benign figure than Walter White. More important, his story is true, and Tony Dokoupil — a senior writer for NBC News, George Washington University alumnus and son of a man responsible for distributing “at least fifty tons” of cannabis during the years that “spanned the drug war from Nixon to Reagan” — brings to it the rigor of a seasoned journalist and the rollicking prose of a kid who clearly inherited a healthier version of his old man’s zest for adventure.
“The cocaine cowboys were sportscars, speedboats, discos, machine guns and cleanly shaven faces,” Dokoupil writes, describing types of smugglers who profited happily, for a while, during the “Just Say No” early ’80s. “The marijuana dealers were pickup trucks, sailboats, acoustic guitars, baseball bats, and Pancho Villa mustaches. … The cocaine cowboys murdered cops and bribed judges while marijuana dealers tipped their caps at the law and wished their competitors a happy chase.” According to The Last Pirate, the providers of pot were the most fun-lovin’ criminals around, man, the kind of guys who were beach-bum buddies with Jimmy Buffett, who partied in luxury hotel rooms after a haul had been delivered and who were smart enough to move their contraband-laden vessels during the East Coast regatta season, when the boats carrying marijuana sailed in plain sight next to the clean ones, all headed for ports in Cape Cod, the Hamptons or the Chesapeake Bay.
In a way, the book is its own tip of the cap to the men (and occasionally women) who fueled reefer madness the old-fashioned, sneaking-it-across-the-border way, even when public policy shifted from President Jimmy Carter’s promises of marijuana decriminalization to President Ronald Reagan’s harsh crackdown on all controlled and dangerous substances. Now, as Dokoupil notes, the culture has shifted once again, with pot decriminalization enacted in the District of Columbia and the regulated sale permissible in Colorado and, soon, Washington.
“It’s a business world: aboveboard, sober, boring,” Little Tony says of this new pot order. From that perspective, Big Tony can be seen as a romantic hero of a bygone era, the weed-brokering equivalent of the ink-stained newspaper man undone by the digital era.
But more than one perspective on Big Tony is reflected in The Last Pirate, and that includes the cold-saltwater-splashing reality that he was a drunk, an addict, a lawbreaker with a hot temper, a husband who regularly slept with hookers and a father who once ditched his 4-year-old son in a Disney World hotel room so he could hit the bars of Orlando. Little Tony — who spent his early childhood in Miami and moved to Maryland in his preteen years — was only in kindergarten when Miami Vice first made capturing bad drug guys seem MTV-cool, and 6 when his dad ceased to be a regular physical presence in his life. For years, he had no idea that his father might have been a prime target for Crockett and Tubbs. It wasn’t until five years ago that Little Tony, then 30 and back in touch with Big Tony, finally accessed the court documents that proved his father’s criminal past was a federal case of massive scope.
Given the conflicted feelings that must bubble within the author, now a father himself, there’s an undercurrent of reserve that occasionally runs through this book, especially in the beginning. He recounts the facts of his extended family history, and his father’s in particular, but doesn’t quite invite the reader to emotionally invest in these characters, perhaps because the author is still trying to sort out his own feelings about them.
In later sections, however, especially once Little Tony starts to become a player on this messy stage himself, The Last Pirate turns increasingly poignant. Dokoupil ultimately starts to learn the lesson that every disappointed son learns about his dad, whether that dad moved mountains of marijuana into this country or not: that his failings, however unforgivable, are what make him a human being.
Jen Chaney reviewed this book for The Washington Post.