Book review: ‘The Last Pirate’ by Tony Dokoupil


Tony Dokoupil “Da-ko-pull” is one of the new hosts on CBS This Morning, the morning show that I usually watch. As part of his introduction, he explained that he had been raised in a well-to-do family involved, he had thought, in East Coast real estate. At some point, he discovered that the money his family had was the result of his father being one of the biggest marijuana smugglers in the United States. I later found out that he had detailed his discovery and related experiences in “The Last Pirate.”

Dokoupil explains the “pirate” reference is the similarity in the two activities: smuggling. He explains the “last” reference refers to the recent widespread change in marijuana acceptance and the fact that much of it is now grown locally.

Big Tony, as his father was called, was the central figure in a pot smuggling ring that thrived in the late ‘70s and early ‘80s. It thrived despite the U.S. war on drugs that was in effect in varying degrees during this time. Dokoupil refers to it as the “Great Stoned Age.” The best marijuana was smuggled in from Columbia by boat, by plane and any other method that could be devised. It was not easy to bring in tons, and that’s what they were doing. It required growers, buyers, shippers, people to unload, transport and storage. This was all before it was retailed and marketed.

The market was large and growing in all classes of people. College campuses were great consumers of the product, but so were working people. Seemingly, everyone wanted the freedom of thought that pot brought.

According to Dokoupil, the marijuana part of the drug culture was quite different from what it seems to be today with the violent Mexican cartels. Few if any guns were involved. The smugglers were simply trying to meet a need and line their pockets. These were the pirates, the people who thrived on the adrenalin of danger. When they succeeded, they were well paid. Dokoupil pointed out that the smuggling community was more afraid of the politician than the police. The police could put you away for a while, but the politician could put you out of business.

Big Tony was a successful smuggler. He was a terrible father and equally bad at monogamy and money management. He took risks to earn the money and risks to spend it: hookers, gambling, drugs — extreme nightlife. Some of the money he buried in Styrofoam coolers, since he was not able to explain the cash to the bank. Some of the money simply disappeared. He became somewhat of mythical figure to his family; young Tony fictionalized his existence to himself and his friends. His mother actually thought Big Tony was dead at one point, although that proved not to be the case.

“The Last Pirate” is Tony Dokoupil’s attempt to determine if he is destined to be like his father. Would fate then pass the characteristics on to Tony’s newborn son? Since at the start of the effort, he knew very little about his father, the whole idea was only a vague fear of the unknown. By the end, he could draw some conclusions about his father, his heritage, an era, the present state of marijuana in the United States, and his relationship to each of these.

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