President John F Kennedy ordered an aide to buy him as many Cuban cigars as he could just hours before he authorised the U.S. trade embargo - which subsequently made them illegal.
Kennedy asked his head of press and fellow cigar smoker Pierre Salinger to obtain '1,000 Petit Upmanns' on February 6, 1962, so he could have them in his hands before they were deemed contraband.
Then, seconds after he was told the next morning that 1,200 of Cuba's finest export had been bought for him, he signed the decree to ban all of the communist state's products from the U.S.
The re-surfacing of the story, initially recounted by Salinger to Cigar Aficionado magazine in 1992, comes with the passing of the 50th anniversary of the embargo yesterday.
JFK, he said, called him into his office and said he needed 'some help' to find 'a lot of cigars'. He wanted '1,000 Petit Upmanns' and needed them by 'tomorrow morning'.
Salinger added: 'I walked out of the office wondering if I would succeed. But since I was a solid Cuban cigar smoker, I knew a lot of stores. I worked on the problem into the evening.
'The next morning, I walked into my White House office at about 8am, and the direct line from the President's office was already ringing. He asked me to come in immediately.
'How did you do Pierre?' he asked, as I walked through the door. 'Very well,' I answered. In fact, I'd gotten 1,200 cigars. Kennedy smiled, and opened up his desk.
'He took out a long paper which he immediately signed. It was the decree banning all Cuban products from the United States. Cuban cigars were now illegal in our country.'
When the embargo began, American teenagers were doing The Twist, the U.S. had yet to put a man into orbit around the Earth and a first-class U.S. postage stamp cost just 4 cents.
The world is much changed since the early days of 1962, but the near-total trade ban has remained the same.
The hand rolled H Upmann cigar brand is one of Cuba's oldest.
Established in 1844 by two brothers, Herman and August Upmann, in Havana.
The Petit Upmann, favoured by JFK, was discontinued in 2002.
The line are medium-flavoured cigars.
They use a unique blend of high-quality tobacco from the Vuelta Abajo region.
Supporters say it is a justified measure against a repressive government that has never stopped being a thorn in Washington's side.
Critics call it a failed policy that has hurt ordinary Cubans instead of the government. All acknowledge that it has not accomplished its core mission of toppling Fidel and Raul Castro.
'All this time has gone by, and yet we keep it in place,' said Wayne Smith, who was a young U.S. diplomat in Havana in 1961 when relations were severed and who returned as the chief American diplomat after they were partially re-established under President Jimmy Carter.
He said: 'We talk to the Russians, we talk to the Chinese, we have normal relations even with Vietnam. We trade with all of them. So why not with Cuba?'
In the White House, the first sign of the looming embargo came when President John F Kennedy told his press secretary to go buy him as many H. Upmann Cuban cigars as he could find. The aide came back with 1,200 stogies.
Kennedy announced the embargo on February 3, 1962, citing 'the subversive offensive of Sino-Soviet communism with which the government of Cuba is publicly aligned'.
It went into effect four days later at the height of the Cold War, a year after the failed CIA-backed Bay of Pigs invasion meant to oust communism from Cuba and eight months before Soviet attempts to put nuclear missiles on the island brought the two superpowers to the brink of war.
Washington already had some limited sanctions in place, but Kennedy's decision was the beginning of a comprehensive ban on U.S. trade with the island that has remained more or less intact ever since.
Little was planned to mark Tuesday's anniversary, but Cuban-American members of Congress issued a joint statement vowing to keep the heat on Cuba.
Supporters of the policy acknowledge that many U.S. strategic concerns from the 1960s have been consigned to the dustbin of history, such as halting the spread of Soviet influence and keeping Fidel Castro from exporting revolution throughout Latin America.
But they say other justifications remain, such as the confiscation of U.S. property in Cuba and the need to press for greater political and personal freedoms on the island.
Jose Cardenas, a former National Security Council staffer on Cuba under President George W Bush, said: 'We have a hemispheric commitment to freedom and democracy and respect for human rights. I still think that those are worthy aspirations.'
With just 90 miles of sea between Florida and Cuba, the United States would be a natural key trade partner and source of tourism.
But the embargo chokes off most commerce, and the threat of stiff fines keeps most Americans from sunbathing in balmy resorts like Cayo Coco.
Cuba is free to trade with other nations, but the U.S. threatens sanctions against foreign companies that don't abide by its restrictions.
A stark example arrived off the coast of Havana last month: A massive oil exploration rig built with less than 10 per cent U.S. parts to qualify under the embargo was brought all the way from Singapore at great expense, while comparable platforms sat idle in U.S. waters just across the Gulf of Mexico.
The embargo is a constant talking point for island authorities, who blame it for shortages of everything from medical equipment to the concrete needed to complete an eight-lane highway spanning the length of the island.
Cuba frequently fulminates against the 'blockade' at the United Nations and demands the U.S. end its 'genocidal' policy.
Every autumn, like clockwork, the vast majority of nations agree, and overwhelmingly back a resolution condemning the embargo.
In November, 186 countries supported the measure, with only Israel joining the U.S. in opposition.
Also each year, Cuba updates its estimate of how much the embargo has cost it, using a complicated - and some say flawed - calculus that takes into account years of interest, the end of the gold standard and other factors.
Last year's estimate summing 49 years of sanctions was $975 billion.
Even some critics of the embargo call Havana's claims exaggerated, saying that while the sanctions had a tremendous impact when first put in place, Cuba was able to adapt and benefited from relationships with like-minded allies such as the former Soviet Union and Venezuela.
Geoff Thale, a Cuba analyst at the Washington Office on Latin America, which supports ending the policy, said: 'There's no doubt that the embargo is detrimental to the Cuban economy.
'It complicates international financial transactions, but more importantly, it limits Cuban families' access to medicine. At the same time, Cuba's economic problems go beyond the embargo.'
While 50 years of socialism have brought advancements in areas such as education and health care, even island authorities acknowledge their perennially struggling economic system must change.
President Raul Castro is in the process of allowing more private-sector activity, decentralising state-run businesses, implementing agricultural reform and slimming government payrolls.
Barack Obama took steps last month to relax travel restrictions on Cuba.
He issued an executive order loosening limits on U.S. travel and money remittances to the communist-led Caribbean nation.
It was an extension of his efforts to reach out to its people.
The measures restore rules in place before former President George W Bush's administration that allowed religious, academic and other non-governmental organisation travel.
But they stop short of lifting a ban on tourist travel by Americans to the island of 11 million people.
The White House says the steps are aimed at developing 'people-to-people' contacts.
It will allow more travel for college professors and students, artists and church groups.
Obama lifted virtually all restrictions on Cuban-Americans visiting their homeland and sending money to relatives in 2009.
The United States actually does have significant trade with Cuba under a clause allowing the sale of food products and some pharmaceuticals.
According to the most recent information available from Cuba's National Statistics Office, the U.S. was the island's seventh-largest trading partner in 2010, selling $410 million in mostly food products.
However, that was down from nearly $1 billion in 2008, as the island increasingly turned to other countries that don't force it to pay cash up front.
Many U.S. businesses would love to be allowed into the Cuban market, but an end to the embargo seems a long way off.
The issue is seen as a political nonstarter in the United States, where every four years, presidential candidates take turns courting the Cuban-American vote in Florida, a key swing state.
President Barack Obama has said Raul Castro's economic openings are insufficient, and it's unlikely he would do anything in an election year to risk losing support in Florida, which he won in 2008.
Even if he wanted to lift the embargo, the Helms-Burton Act of 1996 stipulates that it would have to be approved by Congress.
Raul Castro, for his part, says recent changes in the U.S. such as allowing Cuban-Americans to visit relatives more often and send them more money are merely cosmetic.
Backers of the sanctions say it is as important as ever to maintain what they call the moral high ground, saying islanders will be grateful whenever change does come.
Critics cite the annual U.N. votes to argue that times have changed and the embargo is a Cold War relic that ought to be thrown onto the scrap heap.
'It's no longer a matter of the United States leading a movement to isolate Cuba in the hemisphere,' said Smith, a staunch opponent of the embargo. 'Quite the contrary: If anyone's isolated, on this issue anyway, it's us.'
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