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Son Of A Secret Smuggler Digs Up The Truth About His Dad

If you smoked Colombian weed in the '70s and '80s, Tony Dokoupil would like to thank you: He says you paid for his swim lessons and kept him in the best private school in south Florida — at least for a little while.

Dokoupil's father started selling marijuana during the Nixon era, and expanded his operation until he became a partner in what his son describes as the biggest East Coast dope ring of the Reagan years, smuggling marijuana into the U.S.

But Dokoupil didn't know this until many years later, because his parents didn't tell him. His mother continued to keep the secret after his father disappeared from their lives, when Dokoupil was 10. When he did find out, he wanted to know the whole story. He combed through court documents and newspaper files and interviewed Drug Enforcement Administration agents who investigated the case, as well as more than a dozen smugglers and dealers, including his own father. He shares what he found in a new book called The Last Pirate: A Father, His Son and the Golden Age of Marijuana.

Dokoupil is a senior writer for NBC News. He has reported on the recent changes in marijuana laws, and the new entrepreneurs who are growing and selling marijuana. He tells Fresh Air's Terry Gross about his father's addiction to smuggling and how he ended up retiring.

Interview Highlights

On how he learned about his father's secret drug operation

I was pushing 30 by the time I found out. I had heard rumors that my family was involved in the business, but I thought it was typical hippie stuff. As far as I knew, my father sold real estate in Vermont and had an antique business. ... My mother told me that. That was the narrative. That's what I told other people's parents; that's what I told friends. And then I decided to do a background check on my father. ...

I called the National Archives, which is the keeper of 1 percent of all the paperwork that the federal government produces for all time — the most important things, the things they think historians will care about in the future. I said, "Do you happen to have a criminal record for this individual?" thinking I'd get nothing. Then I get an email with a faxed document inside it a couple weeks later. I click it open, and it's my father's indictment, 1986, for a single job in that year. He was busted for importing and distributing 35,000 pounds of marijuana, which is 17 tons. ... It was enough to roll a joint for every college-age person in America at that time. ... That was a single operation.

On the value of dealers during Richard Nixon's war on drugs

It creates the opportunity to be a hero. Use among his friends and among college kids is going through the roof. The government is trying to take it away; the kids want it; he can provide it.

Timothy Leary in 1969, in an article that was reprinted over and over again, called the drug dealer, the marijuana dealer, one of the three most significant figures of the era — as big as rock stars, as big as underground artists. And then ultimately, he concluded, bigger than both.

On his father's addiction to the thrill of smuggling

In the late 1970s, 90 percent of the marijuana was coming into Florida. It was primarily Colombian; some of it was Jamaican. My father's weed would be delivered to an old fishing shack in the [Florida] Keys. ... It's only one road that connects that necklace of islands and everyone knew that that was the road on which marijuana was smuggled into the country. So to smuggle on that road took an incredible amount of tolerance for risk.

So my father, despite being a partner in the operation, volunteered, for $25,000 a shot, to drive Winnebagos of weed out of the Keys and into America, just for the sheer thrill of it. He had no financial reason to do it. He had no operational reason to do it. ... But by then he was addicted to the sensation of it, to the risk.

On how his father left his family

My father retires. He has, at that point, $500,000 buried in a hillside in New Mexico; he's got a couple of coolers of money on Long Island. He has a safe deposit box with cash in it, plus he has the proceeds from his final job. He's essentially set for life. All he has to do is nothing and it proves to be the only thing he can't do.

Memory is like surveillance footage: Everything gets picked up but you don't really review it unless there's an incident.

He goes to St. Thomas [in the U.S. Virgin Islands] where they rent [a] long sailboat built for 49 people and party with just 12 on it: me and two other kids — smugglers' kids — my mother, one of his partner's girlfriends, an old partner. They have catered meals and tour the island and it's a retirement party. It's a celebration. ...

My father felt uncomfortable in those situations. He felt like he needed more. He needed to be different. So I have a memory of him leaving. We docked the boat, there are days still to come in the celebration, and he walks away. Memory is like surveillance footage: Everything gets picked up but you don't really review it unless there's an incident. So at the time it didn't occur to me that this was the last time I was going to see him in any kind of healthy condition. But in retrospect, that's the last time I saw him whole.

Tony Dokoupil is a former senior reporter for <em>Newsweek.</em>
Seth Wenig / Courtesy of Doubleday
Courtesy of Doubleday
Tony Dokoupil is a former senior reporter for Newsweek.

On how his father's downfall influenced his own sense of identity

Reporting this book and learning what I have about my father was confirming of my own sense of self. So, as someone raised primarily by my mother, I never recognized myself in her. She's wonderful. She's natively wise and accepting in these interesting ways, but she didn't have the same energy I had, she didn't really look like me, our interests didn't always align and I clearly came from some other stock.

My father was not the stock that I wanted to accept for a long time because my only impressions of him were negative. But once I saw what his career was like and how it aligned with the times and the excitement, and how good he was at it, I said, "Oh, OK. That is a nervous system I recognize, in fact."

I don't want to underplay the degree to which it was crushing to go through high school and college without clarity on where you came from and with a sense that your father was an empty vessel. ... The message that society pushes is "like father, like son." ... I felt that there was an inevitability that I would end up like him. ... I had to come to the realization that my father's destiny was one that he selected. ... Therefore, if he can make his life, I can make mine.

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