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The Last Pirate: A Father, His Son, and the Golden Age of Marijuana
A haunting and often hilarious memoir of growing up in 80s Miami as the son of Big Tony, a flawless model of the great American pot baron. To his fellow smugglers, Anthony Edward Dokoupil was the Old Man. He ran stateside operations for one of the largest marijuana rings of the twentieth century. In all they sold hundreds of thousands of pounds of marijuana, and Big Tony distributed at least fifty tons of it. To his son he was a rambling man who was also somehow a present father, a self-destructive addict who ruined everything but affection. Here Tony Dokoupil blends superb reportage with searing personal memories, presenting a probing chronicle of pot-smoking, drug-taking America from the perspective of the generation that grew up in the aftermath of the Great Stoned Age.
274 pages, Kindle Edition
First published January 1, 2014
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October 2, 2019A riveting account of a complicated relationship with a difficult father (who is also a major drug smuggler). A portrait of a time and a relationship.
August 5, 2016
This memoir of “a father, his son, and the golden age of marijuana” promised to be interesting, and it was to an extent. I was completely unaware of Tony Dokoupil, the big-time dope dealer, until I heard of this book. Apparently, lots of stoners were eventually recipients of their share of the tons of weed this dealer was responsible for getting to the country.
To me, the family dynamics of the book was the most interesting part. Multiple generations of abusive fathers raising sons who in turn became abusive, until the author made a conscious decision to break the chain.
Many of the dealers lived by a romanticized “pirate code,” and some ultimately broke that code. The dealer who felt above the fray because he dealt in pot rather than the harder drugs could not resist those harder drugs. He set himself up perfectly for self-destruction. Did he ultimately self-destruct? I'm not telling, but the book will.
The author did tend to over-romanticize much of the story. Sure, parts of it were gritty, but the whole noble undertaking slant got a little old. Some of the writing dragged a bit, and there were a few too many similes, but some of the writing made me smile.
“It helped that he was good-looking, too, with a wide, eager face like a Labrador. In the months to come, she'd realize he also had a Lab's tendency to run off and return sparkly eyes and dirty, radiating love-me-anyway charm.”
About a family member, he writes,
“Once you point a gun at your family, you can lower the barrel, wrap the weapon in blankets, and throw it in the swamp, but you can never get rid of it. The gun is pointed forever.”
The story is interesting, the book is good but not great, and I am glad that I read it, just wish it had managed to be a little less wordy in its telling.
I was given an advance copy for review. The quotes may have changed in the published edition.
To me, the family dynamics of the book was the most interesting part. Multiple generations of abusive fathers raising sons who in turn became abusive, until the author made a conscious decision to break the chain.
Many of the dealers lived by a romanticized “pirate code,” and some ultimately broke that code. The dealer who felt above the fray because he dealt in pot rather than the harder drugs could not resist those harder drugs. He set himself up perfectly for self-destruction. Did he ultimately self-destruct? I'm not telling, but the book will.
The author did tend to over-romanticize much of the story. Sure, parts of it were gritty, but the whole noble undertaking slant got a little old. Some of the writing dragged a bit, and there were a few too many similes, but some of the writing made me smile.
“It helped that he was good-looking, too, with a wide, eager face like a Labrador. In the months to come, she'd realize he also had a Lab's tendency to run off and return sparkly eyes and dirty, radiating love-me-anyway charm.”
About a family member, he writes,
“Once you point a gun at your family, you can lower the barrel, wrap the weapon in blankets, and throw it in the swamp, but you can never get rid of it. The gun is pointed forever.”
The story is interesting, the book is good but not great, and I am glad that I read it, just wish it had managed to be a little less wordy in its telling.
I was given an advance copy for review. The quotes may have changed in the published edition.
January 17, 2022
I found this to be a very interesting book. Took so long to read because some of it is very drawn out. Could have been edited a bit. Feel like I learned a lot about that timeframe.
November 1, 2020
I read this as research for a book I'm writing and I'm glad I did. Fathe-son relationships are often dysfunctional on some level and we can't turn back the clock. Worth a read.
January 14, 2015
This is a good memoir that touches on more than just the life of a Marijuana smuggler. It also touches on father-son dynamics, what it means to have a risk-loving personality, and about the end of an era. I never felt like I wanted to be any of those guys, or even that I necessarily admired them, but they were interesting.
Dokoupil casts the life of a marijuana smuggler in a rosy light, free wheeling loose, fun, good-times with a few bad ends for most, yeah, but one hell of a ride. This isn't exactly a picture I disagree with. I especially loved one scene where he compares the simultaneous images of Nancy and Ronald Regan giving their impassioned speech about how drugs were destroying the youth of America, at the same time that Dokoupil Sr. is pulling of a colossal marijuana shipment. I remember the "just say no" BS that I was exposed to as a child, a pointless boondoggle, a stinky plastic cherry on the sh*t sundae that is America's Drug War. It's nice to have someone poke a finger in that particular eye.
At times Dokoupil depicts his father as a larger-than-life hero, and implies that's how Tony Sr. saw himself. Look at this brave swashbuckler, bringing weed to a pot-starved youth. Dokoupil Jr. the writer, uses lavish description of the weed itself, rich metaphors, like "it looked like sunflowers that had been passed through the digestive tract of a grizzly bear" which makes me wonder if he was writing for, if not as one of marijuana's fans.
As with other books I've read, this book's greatest flaw is also it's most marked virtue: it's lush prose. Dokoupil Jr. may have mixed feelings for his father, but he sure seems to love a good metaphor with his entire being. Some of the metaphors, like the one above (sorry if I've mis-quoted) are brilliant. But, these metaphors come so fast and heavy that they also got in the way, not just in my comprehension, but also in the flow of the story and his own credibility as a non-fiction writer. For example, he writes: "My father walked into a thirty-day rehab in January 1985, feeling like a man one step ahead of the falling piano." It's a lovely sentence, really, but how does Dokoupil Jr. know that's what Dokoupil Sr. felt like? After all, he lost contact with his father for years and years, not seeing Tony Sr. until this particular incident was far, far behind him. And Tony Sr. is a described as a man so addled by drugs and poverty that he literally misplaced half a million dollars and doesn't know where. So how does he remember how he felt on one day thirty years ago?
But if you'll forgive Dokoupil Jr.'s poetic license, and you want to know about the life of one of "the last pirates," pick this memoir up. It's not often that someone with as bizarre a life as Dokoupil Sr. happens to have a son with the literary talents of Dokoupil Jr.
Dokoupil casts the life of a marijuana smuggler in a rosy light, free wheeling loose, fun, good-times with a few bad ends for most, yeah, but one hell of a ride. This isn't exactly a picture I disagree with. I especially loved one scene where he compares the simultaneous images of Nancy and Ronald Regan giving their impassioned speech about how drugs were destroying the youth of America, at the same time that Dokoupil Sr. is pulling of a colossal marijuana shipment. I remember the "just say no" BS that I was exposed to as a child, a pointless boondoggle, a stinky plastic cherry on the sh*t sundae that is America's Drug War. It's nice to have someone poke a finger in that particular eye.
At times Dokoupil depicts his father as a larger-than-life hero, and implies that's how Tony Sr. saw himself. Look at this brave swashbuckler, bringing weed to a pot-starved youth. Dokoupil Jr. the writer, uses lavish description of the weed itself, rich metaphors, like "it looked like sunflowers that had been passed through the digestive tract of a grizzly bear" which makes me wonder if he was writing for, if not as one of marijuana's fans.
As with other books I've read, this book's greatest flaw is also it's most marked virtue: it's lush prose. Dokoupil Jr. may have mixed feelings for his father, but he sure seems to love a good metaphor with his entire being. Some of the metaphors, like the one above (sorry if I've mis-quoted) are brilliant. But, these metaphors come so fast and heavy that they also got in the way, not just in my comprehension, but also in the flow of the story and his own credibility as a non-fiction writer. For example, he writes: "My father walked into a thirty-day rehab in January 1985, feeling like a man one step ahead of the falling piano." It's a lovely sentence, really, but how does Dokoupil Jr. know that's what Dokoupil Sr. felt like? After all, he lost contact with his father for years and years, not seeing Tony Sr. until this particular incident was far, far behind him. And Tony Sr. is a described as a man so addled by drugs and poverty that he literally misplaced half a million dollars and doesn't know where. So how does he remember how he felt on one day thirty years ago?
But if you'll forgive Dokoupil Jr.'s poetic license, and you want to know about the life of one of "the last pirates," pick this memoir up. It's not often that someone with as bizarre a life as Dokoupil Sr. happens to have a son with the literary talents of Dokoupil Jr.
April 16, 2014
The author's father was one of the top weed smugglers (not to be confused with weed carriers) of the 1980s. This makes for an interesting enough story, in the way that almost any story about a drug dealer is at least kinda (but rarely any more than just kinda) interesting, but it feels a little bit short on details, probably because most of it took place before he was born, and the rest of it took place before he was old enough to remember, and the people he interviewed were probably either high the entire time or hiding something.
He probably could have just made something up, and I doubt anyone would have given a shit. As it is, the most dramatic moments involve the father throwing a knife at the mother, from which she apparently recovered (my little brother once did the same thing to my mother, in a restaurant, trying to do some sort of trick), and the kid, as a teenager, buying alcohol for another kid, who got so drunk he almost died (whoa!), but not having to go to jail or anything.
I was waiting for the moment when the father's drug dealing would have some sort of adverse effect on the kid's life, aside from him not having the best pants in the world when he was in high school, but apparently he looks like a movie star, went to college on a baseball scholarship, graduated first in his class (albeit in the business department) and was loaned a ridonkulous sum to go to Columbia grad school. The latter upset him, probably because he was expecting it to be free.
To his credit, he really is a sharp writer. He managed to breathe quite a bit of life into what little story he had to tell here, and I was frequently amused by some of the lines he came up with.
He probably could have just made something up, and I doubt anyone would have given a shit. As it is, the most dramatic moments involve the father throwing a knife at the mother, from which she apparently recovered (my little brother once did the same thing to my mother, in a restaurant, trying to do some sort of trick), and the kid, as a teenager, buying alcohol for another kid, who got so drunk he almost died (whoa!), but not having to go to jail or anything.
I was waiting for the moment when the father's drug dealing would have some sort of adverse effect on the kid's life, aside from him not having the best pants in the world when he was in high school, but apparently he looks like a movie star, went to college on a baseball scholarship, graduated first in his class (albeit in the business department) and was loaned a ridonkulous sum to go to Columbia grad school. The latter upset him, probably because he was expecting it to be free.
To his credit, he really is a sharp writer. He managed to breathe quite a bit of life into what little story he had to tell here, and I was frequently amused by some of the lines he came up with.
June 13, 2014
Not the best, not the worst. Written well enough, but sometimes draggy and confusing, it tells the "truthy" tale of Tony Dokoupil, the author's father, who was a major player in the marijuana smuggling enterprise of the 70's and 80's. The best parts are the author's musings on how he is, or is not, doomed to become his father, as his father apparently had been but the latest in a string of similarly-flawed fathers-and-sons. The worst parts to me are the detailed recreations of scenes where the author was not present, and which seems unlikely to have been described so elaborately later, without any qualifiers.
It also uses the horribly redundant-or-contradictory phrase "one of the only" at least three times, but that's a pet peeve of mine and likely a losing battle at this point...
It also uses the horribly redundant-or-contradictory phrase "one of the only" at least three times, but that's a pet peeve of mine and likely a losing battle at this point...
February 5, 2023
After seeing Dokoupil interview his wife, Katie Tur, about her autobiography and mentioning that they both grew up in dysfunctional families that they hadn't talked about, I decided I needed to read both books. Dokoupil describes his early privileged years as the unaware son of one of the biggest marijuana distributors in the U.S. Dokoupil has done a lot of research about marijuana in the U.S. in the 80's - quality, usage, exporting, law enforcement, etc. (In my opinion, he could have included a little less background.) The information about his family was riveting. At one point, his philandering father left the family and the father and the family went from living the life of a millionaire to being poverty-stricken. Dookoupil didn't see his father for years but reconnected to try and understand why.
June 8, 2020
This is a fascinating bio of Tony Dodoupil's father (the last pirate) but also the story of America's journey in what ultimately ends up as legalization of marijuana. Since I'm old, I actually remember most of what Tony reports on in this book. It is extremely well researched (Tony is a journalist, after all!) and it reads more like a novel; I couldn't put it down. If you are at all interested in the history of our country's attitude toward marijuana you won't be disappointed. It is also a gut-wrenching story of the relationship between father and son, played out prevalently in America no matter what the occupation of the father is. I will loan my copy to a few friends and my daughter but want it back to read again.
November 30, 2022
This was pretty disappointing to read, but I think it's something the son had to write to exorcise his own demons or sense of abandonment.
Who would think that a tale of a swashbuckling pot importer/dealer from the 70s could be dull? I guess it is -- even though I kept thinking sooner or later I'd run into a familiar name down in Miami or Fort Lauderdale.
The book could have focused a bit more on the relationship between the son and father, especially because that is suggested by the title. Sad that after reading the acknowledgements I realize that the author has a different wife and new children so wonder if his first wife's son feels abandoned. H
Who would think that a tale of a swashbuckling pot importer/dealer from the 70s could be dull? I guess it is -- even though I kept thinking sooner or later I'd run into a familiar name down in Miami or Fort Lauderdale.
The book could have focused a bit more on the relationship between the son and father, especially because that is suggested by the title. Sad that after reading the acknowledgements I realize that the author has a different wife and new children so wonder if his first wife's son feels abandoned. H
February 8, 2025
This book almost made me sad at times. It read to me like a young man desperately seeking to understand, and make excuses for the behaviour of his willingly absent father from his life. The author idolized his father, a drug dealer who was more interested in hookers and cocaine, as explained by the author himself, than to take a meaningful part in his, nor his sisters’ upbringing. Beyond the personal reflections of the author, the memoir provides an overview of how the black market drug trade around the world has changed since the 1960’s, and of Nixon’s war on drugs of the 70’s through the perspective of the author. I was kinda bored reading this. DNF.
This entire review has been hidden because of spoilers.
July 26, 2025
Surprised that a recognizable TV News Celebrity would have the gut to publish such a personal reveal as to who his father was, one of the largest marijuana smugglers over 2 decades! BUT I LOVED IT! So many public and political events were aligned with what Tony's father was up to and his ability to make and lose millions in pot distribution. The detailed descriptions of people, locations, social interactions, and the rebel atmosphere of the times (70s-90s) were both familiar and educational as to what was happening in the underground. A keeper of a book, a historical reference for my grandkids.
June 4, 2022
Tony Dokoupil is an anchor on morning news. Looking at him, I could never imagine his upbringing. His father, Big Tony, was a major drug smuggler bringing in tons of marijuana from Mexico and Colombia. For a time there was tons of cash, too. Then it all went to pot. Dad got addicted to drugs, alcohol and his pirate lifestyle. Not a good role for his son.
In addition to the colorful life his father lived, the author tells the story of the marijuana business during the 60s, 70s and beyond. It is quite the tale.
In addition to the colorful life his father lived, the author tells the story of the marijuana business during the 60s, 70s and beyond. It is quite the tale.
June 24, 2022
I've admired Tony Dokoupil on the CBS Morning Show for years, and it wasn't until I read an interview by Katy Tur, his wife and also a news anchor, did I learn that Tony wrote this memoir about his father. What a childhood! His Dad was a major weed dealer in the 70s, back when you could put a suitcase of weed on a plane and it would make it through. There was more information on drug deals than interested me, but the writing is terrific. I was amazed and entertained, and admire Tony's accomplishments despite having a father who was never there, or in jail.
April 14, 2024
3.5/5
This is two books in one - a history of weed, particularly the War on Drugs era, and an account of a son and his (largely absent) father. Who also happened to run the largest marijuana ring of the late 70s/early 80s.
If you are old enough to remember Mexican reefer and/or are interested in the minutiae of The War on Drugs, this book may rate higher than a 3.5 for you.
The father/son story line seemed uneven to me, but maybe that's b/c I'm neither a father nor a son.
This is two books in one - a history of weed, particularly the War on Drugs era, and an account of a son and his (largely absent) father. Who also happened to run the largest marijuana ring of the late 70s/early 80s.
If you are old enough to remember Mexican reefer and/or are interested in the minutiae of The War on Drugs, this book may rate higher than a 3.5 for you.
The father/son story line seemed uneven to me, but maybe that's b/c I'm neither a father nor a son.
May 25, 2025
Half history memoir half sad dad memoir. Equally fascinating. Though there were some boring parts and too many names for me to follow everything and remember everyone involved properly. I think a lot of sections were more for the author as a way to process his feelings than for the reader, but it was still interesting overall. A cautionary tale of living on the edge and getting everything only to lose everything.
September 5, 2021
Great read, much to reminisce
I lived through these years and much of this book was eerily familiar, on a much, much smaller scale. It is, of course, also a memoir and a love story, with some mystery thrown in as Tony tries to uncover so much about his past and attempts to understand his father. Researched as only a journalist can and written with the heart of an author.
I lived through these years and much of this book was eerily familiar, on a much, much smaller scale. It is, of course, also a memoir and a love story, with some mystery thrown in as Tony tries to uncover so much about his past and attempts to understand his father. Researched as only a journalist can and written with the heart of an author.
June 19, 2022
Definitely an interesting story. But I found the book a bit tedious to read. To many similes for my taste and a rather high level of vocabulary. It certainly caused me to understand the concern of how much are you like your criminal father. I thought maybe it would tell me much more about the life of young Tony. I am glad I read it, but I can not say you definitely should.
June 26, 2022
Tony Dokoupil is a journalist that I respect enough to watch every weekday morning; that he is the son of one of the top marijuana sellers of the eighties is absolutely mind bending. This is a story of fabulous highs and devastating lows, and the touching look at a son coming to terms with his heritage. A memorable read.
January 23, 2025
The way he ordered it was weird and the writing can be quiet boring, boring enough to make a book about marijuana smugglers boring. However, the parts analyzing father-son dynamics and generational trauma where good. Also it was fun to read about Southern Miami places that I am very familiar with and their place in the history of the drug war.
February 16, 2018
Interesting! But a little too long - the historical backdrop of this time is especially educational now that we’ve got more “War on Drugs” people back in office. (And I was too young to be aware of it the first time)
January 26, 2019
This story was mildly interesting...I thought that the details of the authors personal relationship with his father dragged on too long. I found the details of the "Smuggle" to be the most interesting along with the outcome of the players in the Smuggle. Well written, jut too long.
January 27, 2020
Written for Drug Dealers
There were paragraphs where the jargon could only be defined by a drug dealer or user on a high. Sorry to see this type of legacy passed on except for its ancestral recognition. Surprised the writing was by a well placed journalist.
There were paragraphs where the jargon could only be defined by a drug dealer or user on a high. Sorry to see this type of legacy passed on except for its ancestral recognition. Surprised the writing was by a well placed journalist.
September 20, 2020
Brave and honest!
I watch Tony Dokoupil on the news every morning and I had stumbled upon this book by accident. I love the way he tells his story, in all of its very vivid detail. Definitely worth the read!
I watch Tony Dokoupil on the news every morning and I had stumbled upon this book by accident. I love the way he tells his story, in all of its very vivid detail. Definitely worth the read!
September 29, 2020
Fascinating story about a whole world happening right under our nose. Reading it made me go back and watch an episode of Miami Vice. The myriad of details, locations, and characters confused me at times, but otherwise a very engaging and worthwhile read.
January 6, 2023
A true life account about a boy and his drug dealing father in the heyday of smuggling. Truth be told, I probably bought pot from his father’s network. Luckily Tony grew up to be a world-class journalist.
August 11, 2023
Interesting and well written. Part history and part psychological analysis. Big Tony is a larger than life character that his son (and most others) will never be able to understand, but many of have either known or observed this type of person. Equal parts destructive and charismatic.
May 6, 2017
Just plain fun, especially if you've lived in California and Miami.
June 4, 2019
Fascinating story from Tony Dokoupil, new news anchor of the CBS this Morning show. growing up with a dad that was a notorious marijuana drug smuggler in the 70's and 80's.
September 23, 2019
Pretty entertaining but boring in a way that all stories about other families are. The parts about the actual smuggling are interesting enough to save the book.
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