On 7 February 1962, U.S. President John F. Kennedy signed one of the most consequential executive orders in cigar history — the United States trade embargo on Cuba. The embargo was meant to punish Fidel Castro’s communist government. Instead, it gave birth to a myth, elevating Cuban cigars from prized luxury to forbidden legend.
But before he reached for his pen, Kennedy reached for his humidor.
According to his press secretary, Pierre Salinger, the night before the embargo was enacted, the President summoned him with an unusual request: to procure 1,200 H. Upmann Petit Coronas — Kennedy’s favourite Cuban cigar. Salinger worked through the night, returning the next morning with the stash. Only then, with a contented smile, did Kennedy sign the embargo order that would make his beloved cigars off-limits to every other American.
It’s one of those stories that perfectly captures the contradictions of politics — part diplomacy, part indulgence, and entirely human.
The Birth of the “Forbidden Fruit”
The embargo banned U.S. residents from buying or importing Cuban goods, including cigars. Overnight, Cuba lost its largest tobacco market, and American cigar makers were forced to look elsewhere for leaf. Many relocated to the Dominican Republic, Honduras, and Nicaragua, where they continued to produce cigars under familiar names — Romeo y Julieta, Montecristo, H. Upmann, and La Gloria Cubana — often using seeds and rolling techniques smuggled out of Cuba.
Meanwhile, back on the island, Cubatabaco, the state tobacco monopoly, continued making cigars under the same heritage brand names. The result? A world where many iconic labels now exist in two versions: the original Cuban-made Habanos and their non-Cuban cousins made abroad.
The American Obsession
With each passing decade, Cuban cigars became the ultimate “forbidden fruit.” To this day, U.S. residents are barred from purchasing or importing them — even when abroad in places like Canada, Mexico, or Europe, where they’re freely sold. This enduring prohibition only fuelled their mystique.
Cuban cigars soon began appearing in American backrooms and boardrooms, often at astonishing mark-ups. Counterfeiting became rampant — experts estimate that up to 95% of “Cuban cigars” sold in the U.S. are fake.
Meanwhile, clever retailers in border towns like Niagara Falls, Ontario, still tempt American tourists with gleaming boxes of Cohibas and Montecristos, displayed just out of legal reach.
A Global Shift in Cigar Culture
While the embargo cut Cuba off from its biggest customer, it inadvertently sparked a renaissance in cigar making elsewhere. The Dominican Republic emerged as a global powerhouse, while Honduras and Nicaragua became renowned for their rich, earthy blends.
In time, Cuban refugees and master rollers established new cigar dynasties abroad — bringing with them generations of craftsmanship and the mystique of Havana’s golden era. Some even argue that these “exiled cigars” rival their Cuban ancestors in consistency and quality.
Easing the Smoke — and Tightening Again
In January 2015, the Obama administration announced a historic thaw in relations, allowing travellers to bring home up to $100 worth of Cuban tobacco or rum — the first legal importation in over half a century.
For a brief, hopeful moment, it seemed as though the world’s most famous cigars might finally return to American shelves. But that hope was short-lived; later policy reversals once again tightened restrictions, keeping Cuban cigars an elusive indulgence for Americans — and an enduring symbol of luxury, rebellion, and nostalgia.
Final Thoughts
From Kennedy’s secret stash to the thriving cigar cultures of Nicaragua and the Dominican Republic, the U.S.–Cuba trade embargo reshaped the cigar world forever. What began as a political sanction became a story of resilience, craftsmanship, and enduring desire.
For many cigar lovers, the allure of a Cuban Habano still lies not just in its flavour, but in the story — a tale of passion, politics, and forbidden pleasure that continues to smoulder more than 60 years later.
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