Robb Report Vices

The Incurable Cuban Crisis

The story is legendary among cigar enthusiasts: In 1962, with the stroke of a pen, President John F. Kennedy signed a decree banning the import of all Cuban products to the United States. This, of course, included cigars. Before instituting the new law, however, the president surreptitiously instructed his press secretary and fellow cigar smoker, Pierre Salinger, to buy more than 1,200 Petit H. Upmanns on Kennedy’s behalf.

More than 50 years later, the embargo with Cuba is as resolute as ever, which leaves American cigar devotees struggling to find a way to enjoy Havana’s finest export on their native soil. After all, while no cigar—whether it’s Dominican, Nicaraguan, Honduran, or any other regional offering—tastes like any of the others, nothing tastes like a Cuban. For that reason, many brave world travelers have taken their chances with U.S. customs and border patrol for years; and some have come away with entertaining—and in some cases, improbable— success stories.

One passionate smoker, for example, recounts a time when, after decades of traveling around the world and regularly bringing illegal Cuban cigars back into the country, he was finally stopped in Chicago. His late-night flight from some exotic destination was mostly empty but, unfortunately, that only increased the odds that a customs agent would target the cigar enthusiast. Sure enough, he was searched. What’s worse, this anonymous cigar smoker was traveling—as he typically did—with illegal smokes. Upon opening the traveler’s suitcase, the customs agent found three, 4-packs of Cuban cigars and shot the traveler an annoyed glance. “Do you have any idea how much paperwork I would have to fill out for 12 cigars?” he asked. Returning the smokes to the suitcase, he sent the enthusiast on his way.

Fortunately for the traveler, the agent didn’t search his briefcase. If he had, the agent would have found three full boxes of cigars.

There are other brazen accounts, as well, such as a story about a cigar collector who vacationed in Mexico with friends and chose to pack all of his clothes in his friends’ bags so that he could use his own suitcase exclusively for Cuban cigars. “If you breathed too hard on this thing, cigars would have popped out,” he recalls. But he, too, narrowly escaped a potentially damning altercation with a customs agent.

These success stories prove that traveling home to the States with Cuban cigars can be done, but we admit that it’s a risky play. Moreover, it’s also against the law. As an alternative solution, online retailers such as Top Cubans or Lewis Stagnetto Ltd. can deliver you those illicit cigars—the modern epitome of forbidden fruit—and will replace any Customs-confiscated puros. In that respect, the risk is negligible, but the confiscation of illegal cigars with your name and address in the recipient’s box could lead to years of aggravation if the federal government should choose to add your name to its watch list.

Technically, pre-embargo cigars (those made prior to February 1962) are legal to carry back into the States. In fact, a handful of lots in the London cigar auction hosted by C.Gars Ltd. in November are of this pre-embargo variety, which makes them tempting, even with the lofty prices that they are certain to achieve. But even with all the proper documentation, you may find it difficult to convince a customs agent that the Cuban cigars in your possession are not of the confiscating kind.

Paying more than $4,000 for a box of 25 cigars and taking your chances with U.S. Customs? Yeah, we’d say that’s living dangerously.