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Tony Dokoupil on Miami's Golden Era of Marijuana Smuggling: "Pot Today Is So Boring"

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Scarface. Cocaine Cowboys. How to Leave Hialeah. Now Miamians can add a new title to their list of must-haves: Tony Dokoupil's The Last Pirate.

The book's subtitle says it all: "A Father, His Son, and the Golden Age of Marijuana." Dokoupil, a reporter for NBC, will speak about his gripping, sometimes hilarious memoir this Sunday at the Miami Book Fair International. Beforehand, he spoke to New Times about the longing he feels for South Florida's long-lost era of pot smuggling, despite the way the business tore his own family apart.

"I'm nostalgic about that era of marijuana because I think it was the final era in which we had criminals in this country who were truly larger cultural figures," he says. "Pot today is so boring. It's such a field of guys in suits with dimpled ties and square jaws and creeping bellies from too many steaks."

Here is a lightly edited transcription of our Q&A with Dokoupil:

New Times: Miami plays a central role in your book. How do you feel about it now, so many years after you left?

Tony Dokoupil: I love it. I wish I never left. I think frequently about how my life would have been different if we had never left... it's just a goddamn wonderland. It's a great place to be a kid and it's an even greater place to be a teenager. And then to be a young person there and to navigate that city, it's just America's most exotic interesting city. It's also been able to pull in -- in part because of the legacy of the 80s -- all this fantastic culture, the Miami International Book Festival, for example. There are just things to do. It's so great. I really feel like I was robbed of what should have been a native right to that place, and now i'm a tourist like anyone else.

It's funny, I'll have these conversations where people will ask where I'm from and I'll say Miami. And then they'll ask me, "Do you know..." and I'll say, "Well, shit, no. I don't know that at all." Because I didn't know it other than a kid violating the local shirt and shoes laws in the local convenience store.

It's a weird place full of weird and fascinating characters, like your dad.

Yeah. Miami is definitely a place where you want to have a conversation with the guy on the barstool next to you because it's not going to be a boring one.

Funny you say that. I was just eating lunch the other day and the guy sitting next to me claimed he was a boat captain who ran kilos of cocaine around the Caribbean back in the '80s.

It's not so preposterous, right? In the 1980s, Reagan said he busted 10,000 traffickers. There were more than 100,000 supposedly in the country, which is an astoundingly large number, and a lot of them were in Miami.

Reading the book, I got the sense that you have a strong sense of nostalgia for this era of marijuana smuggling, despite the way it wrecked your own childhood.

Yes, and you're right to pick up on that. I look longingly on the era of smuggled marijuana. As we enter into the era of much more corporate pot, it is depressing. I know a lot of people are happy that smokers don't have to hide themselves and that sellers can be celebrated and out in the open now, but marijuana was basically the only thing in America that became a cultural hit in the absence of some kind of corporate machine behind it. It was a truly thing of the people that grew organically and spread person to person. There was no marketing campaign. There was no celebrity endorsement, that somebody was getting money for at least. And that kind of purity is fucking rare, it's so unbelievably rare.

I was talking to a Harvard professor today for a pot story, in fact. She's a big expert on advertising. And I said, "Can you think of any other product in American history that has the same foothold as marijuana in the absence of mass marketing?" And she could not. It is special, and now that era of specialness is over. And I'm sad about that, because I'm kind of anti-corporate.

Pot today is so boring. It's such a field of guys in suits with dimpled ties and square jaws and creeping bellies from too many steaks -- people who, if they live the life they want to live, will never have a low point. They will only get higher, in terms of success.

That kind of life feels boring to me. It really does feel boring to me. I like the process of great swings of fortune. It just feels like a bigger existence, an existence that was more common not only if you were a criminal but just in generations past.

It definitely does seem like a much different America. States are legalizing pot left and right. Even Florida almost OK'd medicinal marijuana a few weeks ago. But when you're dad did it, pot smugglers were amiable outlaws. They were almost asking to be caught.

I'm convinced that for a certain kind of criminal, getting caught is part of the point, because you think you're smarter than the man, and you think you're a hero and that you're justified. And the only way for any of those beliefs to be validated is for you to get caught and for it to be a big deal and for people to talk about you -- for your name to be on people's list years or even decades after your exploits are over.

That is what they are aspiring towards. It's not about money. My father is totally, straight down the line typical. I talked to more than a dozen smugglers. And they had echoes of the same story over and over again. They always pushed it too far, not for money but for the experience and because they wanted to taste the other side. They want that clap. They want the applause at the end. They really do.

The other reason that i'm nostalgic about that era of marijuana is because I think it was the final era in which we had criminals in this country who were truly larger cultural figures....

Today's criminals are hackers and leakers and people with immense technological savvy and their exploits are massively important and influential. But the scenery and the personalities and the exploits seem somehow smaller. They don't have the same level of physical courage involved. The backdrops are basements instead of mountain tops.

That feels like a very significant break in the history of this country. For decades if not centuries we had a recognizable outlaw for each generation, and that person was operating out in the big wide world, not in a room through cables and tubes. And that's a change. Me being kind of romantic and nostalgic, that's a change that I'm kind of bummed out about.

Yeah, hackers don't have the same mystique about them as marijuana smugglers.

Every time hackers are busted, I always read the story because I'm looking for that paragraph where the cops talk about what they found in the apartment. Because when smugglers were busted in Miami in the 80s, very often they would find on the shelf a VHS documentary about gangsters from the 20s. There was an obvious connection. Or coke dealers, they would break in the door and there would be a Scarface poster there. They were identifying with a very clear character. They were trying to be a certain kind of person.

I've seen no sign that today's hacker types are aspiring to be a figure like that. Maybe that figure has yet to emerge and ten years from now everybody will have posters of the Wikileaks guy. Maybe he will be the poster on everybody's walls in ten years. But so far that doesn't seem to exist yet. They don't seem to be self-referential in that way.

Maybe part of the problem is that today's top criminal are al-Qaeda and ISIS: groups that are supposedly unredeemable and completely alien to us.

It's hard to be a lovable countercultural figure these days because, yeah, you're right, the people who radiate with pure evil are not drug dealers anymore, they are actual terrorists. And those people, for the most part, come from outside the culture. They don't come from the inside.

Another issue in the book is your father's failure as a dad, his decision to choose drug smuggling over parenting.

He felt like he had a career ambition, and if that took him from his fatherhood duties, he was still of the era that that didn't matter. As long as there was money in the bank account and I had my tuition bills paid and a vacation that year, that was all that mattered. He could pour his talents into whatever, whether it was getting his name on a building in New York or getting another load into the country, that was fair game as long as I was paid for. That was the way they conceived of it. It's sort of sad. He was of that last generation of fathers who had that conception of the job.

You also write about your determination to be a better, different father than your own dad was. Do you worry that you are similar in any way, or that you will follow in his footsteps somehow?

I'm discovering that it is very hard to be passionate about a job. I would say that I'm as obsessed with my current pursuits as he was with his. And I find them somewhat comparable.

This will sound totally crazy but he used to talk about the thrill of pulling in a load and then knowing that it was being sold and that people were responding to that. Well, that's not all that dissimilar from what you and I do [as reporters]. You get a story, you get loaned money to go find it, maybe you do maybe you don't. If you do, it's really fucking exciting. You have it and then you distribute it and people are like, "that's awesome." Or they are happier or they are different. They feel something.

That's a very powerful thing to have in a career. He got carried away with it. I'm at risk of getting carried away with it too. I probably spend way too much time thinking about work stuff and not enough time thinking about playgrounds and diapers.

Was there ever a point at which you thought about abandoning this book project?

I personally had no reservations but people in my family had reservations and there were arguments over why we would air this history. And they were strident enough arguments that the project wobbled a little bit. I had to think about whether I really wanted to wobble through this 100-yard sewer.

Ultimately, I felt like decisions had been made about how my life would be when I was a kid, so I'm going to take agency now and decide to tell this story. I didn't have a choice of you as parents, but now I have a choice as an adult whether to tell that story and you guys don't have a say anymore.

How did your parents react to the book when it came out?

My mother was fine with it ultimately. She understood and is glad that it's over. My father's reaction was pretty hilarious. He writes mysteries now in Cambridge [Massachusetts]. They don't get published but he's got talent as a writer. He could have focused and done differently in life and been OK, I think.

He read the book and first he listed 15 typoes or sentences that he didn't think were as sonorous as they could be. And then he said, "I don't think you really got."

"I didn't get it? What the hell do you mean?"

And he's like "I don't think you really captured what drove me."

I said, "What do you mean?"

And he said, "It was about the sex, Tony."

"It's about the sex?"

He said, "Yeah, there's not enough hookers. Not enough hookers."

Meanwhile, I'm thinking fucking hell. There's at least five scenes with hookers. There is a fivesome in the book. I mean that was the hardest paragraph to write: a description of my father's sexual goodtime with two women in St. Thomas. Ugh. It's tough to even think about. For some reason, I can't even bear to tell you about it.

So yeah, my father's response was, "I don't think you got it. Not enough hookers."

I've actually been really heartened by the response. I've been contacted by a bunch of smugglers from that era who have written me and said, "You know, my wife gave me the book and I thought it was going to be a bunch of bullshit but you really did get it." So that means a lot to me. I haven't heard from anybody who says that I didn't capture the era, and that was my goal.

Do you think of yourself as incredibly lucky or incredibly unlucky? I mean, your father put you and your family through hell. But as a journalist, you basically walked into the most amazing story.

I think life could have gone terribly for me, and for reasons that I don't quite understand, I have not gone into the gutter. And given that luck... for whatever reason I have not had my own struggle with alcohol or drugs. I've had a very stable mind.

If you have that as a foundation then it [this story] is an absolute gift. How lucky? I was so overjoyed to get the indictment. When it got emailed to me, I opened it up and it was a job [indictment against my dad] for 17 tons [of cocaine]. I was like, "Hoo ha. This is a fucking story." I knew that I had something.

This was a personal pursuit and I did have things that I wanted to settle about where I came from, but at the same time, this was a story I would have been interested in telling even if it had nothing to do with my family.

There have been a lot of books about smugglers, but the problem with most books about smugglers is that they are written by the smugglers themselves. So they have a key-hole view, and they have all kinds of blind spots and they don't capture the bigger picture.

What I tried to do on every page of the book was think about how [my father] is operating in a bigger context of cultural, social and legal [issues] and how is he reacting to his surroundings? And then make it representative so that he is a stand-in for the thousands of people like him.

Because there really were [thousands of other smugglers]. The only thing that made him special was that he did it for long. I think there were 15 years where it was his only income.

Typically the career span of smugglers and dealers is comparable to an NFL running back: it's like two seasons. And so to have a long career and to move in circles that were really big and real weight behind them made him special.

Tony Dokoupil will speak about The Last Pirate: A Father, His Son and the Golden Age of Marijuana alongside Michael Deibert (The Gulf Cartel and the Price of America's Drug War in Mexico) on Sunday at 5 p.m. in Room 8301.

Send your tips to the author, or follow him on Twitter @MikeMillerMiami.

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