A Secret History of Cuban Contraband
President Kennedy ordered the US embargo against Cuba on October 22 1962, but not before hoarding over 1,000 of his favourite cigars…
“Socialismo O Muerte”.
Spray-painted on walls, plastered on billboards and accompanied by profiles of Fidel Castro and Che Guevara in faded green fatigues, “socialism or death” was the slogan that represented the winds of sweeping change in Cuba during the late Fifties.
By the time this revolutionary gust had become a howling communist typhoon, not everyone was enjoying the weather forecast from Havana. In 1962, a year after a failed attempt to overthrow Castro’s government at the Bay of Pigs, President Kennedy tried to stifle one of his closest neighbours with a crippling embargo banning all trade between the two nations.
But before signing a divorce bill that would ensure no US President would make the short journey across the Florida Straits for another 50 years, JFK had some personal business to attend.
He summoned his press secretary Pierre Salinger into the Oval Office and requested that he source 1,000 H. Upmann cigars, produced by Cuba’s state-owned tobacco company Habanos SA. Kennedy needed them by the following morning.
A keen smoker, Salinger accepted the presidential challenge. After spending a day emptying every humidor he could find in Washington DC, he returned to the White House the next day with 1,200 Petit Upmanns.
After taking delivery of his bounty and with Salinger still in the room, Kennedy produced a freshly-drafted executive order invoking the Trading with the Enemy Act, upon which he scrawled his signature. It was February 7th 1962, and it was now illegal to bring Cuban products — including cigars — into the United States.
The long-term effect of the embargo, known in Cuba as el bloqueo, has seen parts of the country frozen in time. Some 60,000 classic American cars populate Cuba’s roads, only half of which are paved. Shipped from Detroit over 50 years ago, the fact that many of these Cadillacs, Buicks, Fords and Dodges are still roadworthy today is not only testament to the durability of the Yank tanks, but also to the ingenuity of the Cubans who’ve maintained them. Nowhere else on the planet will you find a Russian Lada engine hiding in the bonnet of a ’59 Chevy Impala. It’s hard to disagree with the Cubans who claim that they’re not mechanics, but magicians.
The US embargo discouraged other international partners from dealing with Cuba, meaning the Caribbean nation relied heavily on its Soviet friends to stay afloat. When the USSR collapsed in 1991, Castro and Cuba were cut even further adrift from the world.
“We have serious food shortages and all material stuff is hard to get. One day we have it supplied and the next day we have nothing,” explains Alejandro Alonso, a tour guide at Cuban Compass.
“In Cuba, you learn to never take things for granted. If you need something, you have to be ready to find it.”
Alonso describes how US products still find a way in, thanks to smugglers risking the wrath of customs officials. Describing them as “brave soldiers of solidarity and love”, he cites Lucius Walker as one such example. A New Jersey reverend, Walker founded the Pastors for Peace movement in 1992, organising annual caravan trips to Cuba to provide what he called friendshipments. They included medicine, computers, bicycles and school supplies.
Walker travelled through Mexico to avoid friction with US officials, though made no attempt to hide his caravans nor his opposition to the blockade. When he died in 2010, his ashes were scattered on Cuban soil.
Today, in downtown Havana malls and street markets off Varadero beach, American goods are not as rare as one might expect. Branded clothing, electrical goods and sports equipment arrive via entrepreneurial Cubans with Spanish passports and access to Panama’s duty-free zone.
“For a Cuban to be a mula is not bad or compromising, and has nothing to do with drugs,” explains John Ahrens, director at Cuban Adventures. “It is even a quasi-legal business, now that the Cuban government allows citizens to be importers of merchandise once a year with a capacity of up to 120 kilograms.”
“It is easy to see how a Panama or a Mexico flight takes hours in passing through customs because of the long line of Cubans with piles of bags and huge TV screens.”
“Before all this, back in the ‘80s, I remember people visiting from La Comunidad (exiled Cuban communities in Florida) found creative ways to bring more luggage. They used to wear layers of clothes, with four or five jeans on top of one another and six or seven shirts… everyone on the plane here looked fat and sweaty for a reason.”
Over the years, Cubans have also become adept at satiating cultural cravings, regardless of the political climate. American television and movies are shared via micro USB drives, pop-up “arcades” appear in the homes of the lucky few who’ve sourced a PlayStation or Xbox, while an underground street network known as SNET connects around 20,000 tech-savvy Habaneros, outside of the government’s purview.
In music, Cuban hip-hop flourishes in the same protest tradition as its Bronx cousin, while the legacy of Son Cubano lives on through the world-famous Buena Vista Social Club, the Havana ensemble brought together in 1996 by Californian guitarist Ry Cooder. In side-stepping the embargo by entering Cuba via Mexico, Cooder is one example of the many Americans refusing to miss out on what Cuba has to offer the world.
Cuban music may have found its way into American hearts, but it is the products that have embedded into America’s soul that have caused customs officials the most consternation. The US consumes over 40% of the world’s rum, but unless they’re prepared to follow in the footsteps of Ernest Hemingway and cross the Straits to enjoy the fruits of Cuba’s sugar canes, a Havana Club Mojito — with its rich vanilla, crisp citrus and refreshing mint notes — will never touch their lips.
During the years of Prohibition, long before the embargo, rich Americans would spend weekends in Havana just to sip this Cuban elixir. When President Calvin Coolidge visited Cuba on an official visit in 1928, his entourage succumbed to temptation; journalists, diplomats and officials filled their suitcases full of rum. Ever the straight-shooting puritan, Silent Cal did not — like Kennedy 34 years later — engage in such vices.
Yet whatever prestige Cuban rum enjoys, it pales in significance to Cuba’s most famous export. Cigars are not only its most prized asset; they are ever-present throughout its tumultuous history.
It is said that when Che Guevara reached out to the USA about a rapprochement, he did so by sending JFK a mahogany box of cigars, sealed with the Cuban flag. The Americans weren’t so friendly in return. According to Cuba’s former counterintelligence chief, Fabián Escalante, the CIA attempted to assassinate Fidel Castro by poisoning a box of his favourite smokes. Given Castro lived until he was 90, it’s clear he had no troubling spotting a sub-standard Cohiba. After all, Cubans were old hands at this.
When Christopher Columbus discovered Cuba in 1492, he found the locals smoking tobacco wrapped in palm leaves. Before the end of the 16th century, the Spanish had set up the world’s first cigar factory in Cuba.
Even in spite of Cuba’s trading restrictions, its competitors are still playing catch up. In much the same way as French claret is deemed naturally superior wine, Cuba’s unique ‘terroir’ — the microclimate factors influencing the tobacco’s genetic quality — is what is believed to set it apart. The mineral-rich soil in the plantations of Cuba’s Vuelta Abajo region, located in a valley at the far west of the island, is considered by aficionados to produce the best cigar tobacco in the world.
Then there’s the production process. At the Corona Cigar Factory on Havana’s popular Galiano Street, visitors are invited to observe as 600 workers sit at individual wooden desks, hand-rolling over 150 cigars a day. Despite the production line layout, the atmosphere is relaxed; workers smoke, laugh and listen as a lady reads out from the state newspaper. Training can take five months, but for Cubans it is a skilled — and comparatively lucrative — practice. The best rollers earn more than doctors.
It’s no wonder then, that from the moment President Kennedy secured his own stash of contraband, fellow stogie-loving Americans have spent the last 50 years trying to follow his lead. They’ve not always succeeded.
Despite attempts by Barack Obama to improve the US relationship with Cuba, including a historic visit in 2016, US citizens are still not permitted to travel there as a tourist.
Instead, they must meet one of 12 criteria for entry, including family visits, journalism, sporting competitions or “support for the Cuban people”. It is this latter category that most closely aligns to the traditional concept of tourism, though it does come with caveats, usually as part of a licensed tour with guides who will advise where money should and shouldn’t be spent. Helping private individuals — such as those who run local restaurants and homestay casas particulares — is encouraged. Throwing Dollars at state-owned businesses is not.
“President Obama was very good for us to understand the difference between American people and the American government,” says Alonso.
“We had the chance to get in touch with American people, and we discovered that they are just like we are.”
Returning US citizens are subject to restrictions on the Cuban products they bring back Stateside. The specific quantities permitted have varied over the years, but any cigars and rum brought home must be for personal use only.
Those who’ve “forgotten” this important distinction have sometimes received reminders in court. Violating the Trading with the Enemy Act carries a maximum penalty of $250,000, and ten years in jail.
In 1996, real estate developer Joe Hybl thought it was worth the risk. He returned from his first trip to Cuba with 15 boxes of cigars to sell to friends and colleagues. By 1997, emboldened by how easy it had been to bypass customs, he was regularly Cuba-bound, sometimes with up to $40,000 in cash. He’d return via Mexico, then sell his Cuban souvenirs to Americans at mark-ups of up to 800%.
Before long, the first ever federal investigation into Cuban cigar smuggling, suitably code-named Operation Smoke Signal, ended with Hybl receiving a $38,000 fine and probation.
If his slap on the wrist was meant to deter others, it didn’t work. In 2002, a tip-off from his ex-wife saw lawyer Richard Connors stopped at the Canadian border with four suitcases of Cuban cigars. He served 37 months in prison for violating the Act along with falsifying his passport and conspiracy. Unsurprisingly, he was also disbarred.
In 2008, Douglas Hiner’s 53-foot sailboat was intercepted by the US Coast Guard and found to be carrying hundreds of Cuban cigars and cigarettes. A further investigation led to a Florida storage centre where more than 28,000 Cuban cigars and 42 bottles of Cuban rum were found.
Hiner, sentenced to three-years’ probation, admitted: “obviously, I wasn’t a good smuggler. But it was a victimless crime. Essentially it was a political crime.”
By the turn of the 21st century, the Cuban cigar smuggling business was worth an estimated $100m. “It’s the forbidden fruit,” said US customs spokesman Michael Sheehan in 1997. “Cigars have become tremendously popular, and Cuban cigars are legendary for their quality. You have a natural supply and demand.”
As an experienced businessman, Donald Trump knows a thing or two about supply and demand. But while Obama’s relationship with Raul Castro was described as the Cuban Thaw, Trump has favoured putting his socialist neighbours back in the freezer.
“The embargo is still very much in place today, as strong as it has ever been,” says Ahrens. “And it has been reinforced by the Trump administration, with threats to strengthen it even further. The embargo is written into the US constitution, so for it to be removed, legislation needs to pass both houses of government”.
For now, Cubans will continue to rely on their ingrained resourcefulness, bolstered by years of resilience. As for frustrated Americans? They may want to consider the words of Fidel Castro after he gave up smoking in 1985:
“The best thing you can do with this box of cigars, is to give them to your enemy.”
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