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The luxurious Hotel Nacional overlooks the entrance to Havana Bay on the north shore of Cuba. The twin-spired landmark has hosted a formidable array of celebrity guests since it opened in 1930, Winston Churchill, Ava Gardner, and Johnny Weissmuller among them.
On a balmy day in June 1996, three lesser-known travelers found themselves in conversation at the hotel's palm tree-lined pool. Each of the three men was from Northern California. Each visited Cuba frequently. And each had a certain mischievous gleam in his eye, a hint of pirate blood that said he wasn't above slipping something past the law.
The first, an attorney, considered himself a connoisseur of Cuban tobacco, and approached his hobby with great thoroughness. He cultivated friendships at Havana's legendary cigar factories, and when it came time to return to his wife and family in Sacramento, he always snuck a few boxes of cigars through U.S. Customs.
Cuba: What You Need to Know About the U.S. Embargo
U.S. Department of the Treasury, Office of Foreign Assets Control
The second, a real estate developer from Atherton, smoked only an occasional cigar himself, but had developed a successful business smuggling them from Havana into the U.S. and selling them to well-heeled aficionados.
The third, a son of wealth with time on his hands, treaded water in the Hotel Nacional pool as the three men talked. He was already working with the real estate developer, smuggling loads of cigars through customs 25, 50, or 100 boxes at a time.
By the conversation's end, common ground had been discovered. Each man smelled opportunity, and sensed that the future held a potentially profitable convergence of mutual interests. The three travelers shook hands, exchanged phone numbers, and promised to stay in touch.
None of them could have anticipated that, before long, one would betray the others to save himself. Over cigars.
As Portugal is known for port wine, and Germany for beer, Cuba is known for producing the ultimate cigar. The Vuelta Abajo region, about 100 miles west of Havana, provides the world's best climate and soil for cigar tobacco. Every major cigar company has 19th-century origins in Cuba, and after the U.S. slapped a trade embargo on Cuba , most opened factories in U.S.-friendly countries like the Dominican Republic. In the early 1960s, Fidel Castro even founded his own Cohiba brand, now the most recognizable name in cigars.
The U.S. government seems completely high-strung in how it deals with Cuban cigars. That's because the U.S. is completely high-strung in how it deals with Cuba itself. The relationship between the two countries is unlike any other in the civilized world.
Things grew frosty after Castro's revolutionary army overthrew Fulgencio Batista in 1959. Apprehension over a Communist enclave so close to U.S. shores led to the 1961 Bay of Pigs fiasco, which was followed by the missile crisis. After President Kennedy faced down Russia over that one, he decided to put financial pressure on Castro by placing an embargo against all Cuban goods, including the world-renowned cigars (but only after Kennedy assistant Pierre Salinger safely procured 1,200 of JFK's favorite Upmann petits).
With subtle variations added by Presidents Ford, Carter, and Reagan, the embargo has remained in place. The U.S. still considers Cuba an official enemy, on a short-list that includes North Korea, Libya, Iran, Iraq, and Sudan.
Thirty-plus years of sanctions have squeezed the island dry. Families are allowed one roll of toilet paper and one bar of soap per month. A doctor makes the equivalent of $20 a month. Cubans who moved to the States regularly send money to their families left behind.
Through all this, Havana has taken on the personality of a demented border town, where a suitcase full of cash speaks loudest in an aggressive black market economy. Businesses prefer U.S. dollars over Cuban currency. Locals roam the streets, dodging vintage Chevys and beat-up Soviet sedans, lugging sacks of fresh lobsters, one for a dollar. Families rent their homes to visitors for $20 a night, including dinner. Teenage girls look for middle-aged male tourists to buy them dinner and purchase other services.
U.S. citizens trying to visit Cuba get little encouragement from their own government. Only journalists, researchers, and others approved on a case-by-case basis by the Treasury Department's Office of Foreign Assets Control are legally allowed to go. Those authorized by the OFAC to visit can spend only $183 per day for living expenses, and bring only $100 worth of Cuban goods back into the States. Violating the rules can bring up to 12 years in prison, and over $1 million in corporate fines, or $250,000 in individual fines.
But telling an American he's not supposed to do something is as good as telling him he is required to do so. Yankee tourists regularly slip into Cuba through neutral countries like Mexico or Canada, hiding their visits by intentionally forgetting to have their passports stamped. They hit the island for sightseeing and scuba diving, then figure out how and what they're going to sneak back into the States.
Mostly, it's cigars.
Fetching $25 to $50 apiece in the U.S., Cuban cigars have always been an indulgence of the wealthy. In 1997, California Rep. George Miller, a Democrat from Martinez, stood on the floor of the U.S. House of Representatives and proposed exempting Cuban cigars from the embargo. Miller passionately cited the inherent hypocrisy of politicians who earnestly back the law, while laughing it up in rooms filled with fine Cuban cigar smoke. His proposal prompted spirited debate among colleagues, but ultimately went nowhere.