By Karl Vick
July 1, 2015

There’s a new flagpole outside the stately Washington D.C. building that will become the Cuban Embassy later this month—and that’s a win to be savored by President Obama, who has made outreach to enemy states a main point of his foreign policy. But if flagpoles are the symbol of the day, take proper note of the forest of 138 staffs outside the Havana building that will house the U.S. Embassy. The flagpoles were placed there nine years ago by the Cuban government, to physically impede the view of the building, a mostly empty seaside edifice Washington had decided to turn into an electronic message board aimed at speaking directly to the Cuban population.

That sophomoric level of exchange is precisely what both governments have said they aim to leave behind, over the six months since Obama and Cuban President Raul Castro announced the surprise rapprochement. The leaders managed to speak to rather than past each other at the hemispheric summit in Panama in April, and U.S. and Cuban officials got on well in the series of private negotiations that produced Wednesday’s announcement. Secretary of State John Kerry will go to Havana on July 22 to formally convert the U.S. Interests Section to the U.S. Embassy. And the White House says Obama is among the Americans curious about seeing the country for himself; look for him to visit before his term ends.

But away from the large gestures and sweeping statements, the reality on the ground remains stubborn. Relations between the countries were cut off in 1961, and it’s not as though things stood still for the next 54 years. Both countries were busy producing a jungle of laws, regulations and procedures intended, like that forest of flagpoles, to act as obstacles to normal contact. And jungles are not easily untangled.

Obama’s administration did what it could in the first weeks after the December announcement, using executive authority to remove penalties for Americans to travel to Cuba—as long as they did not call themselves tourists. Airline charters are now permitted from many U.S. cities, and passenger ferries from South Florida. But a thicket of impediments remain. The four biggest:

1. The embargo: As Obama made clear in his Rose Garden remarks, the chief executive is powerless to undo the overlapping legislation that bars U.S. citizens and companies from doing ordinary business with the island. Only Congress can repeal the embargo, and that’s one place where the Cuban expatriate lobby—dominated by staunchly anti-Castro Cubans who fled the island after Fidel took power in 1959—has yet to be tested. Presidential contender Sen. Marco Rubio, the Florida Republican, has made himself chief spokesman against making any change.

2. Guantanamo: Obama’s promise to close the controversial prison on Guantanamo Naval Base does not mean the U.S. has any intention of giving up the base itself, which it’s leased from Havana since 1903—on terms Washington dictated, in the Big Brother role it played in Cuban internal affairs before Castro. But Castro’s government has never cashed the rent checks. Both for reasons of sovereignty and credibility as anti-imperialist stalwart, Cuba wants the land back.

3. The Internet: The announcements by Netflix and Airbnb that they would be operating in Cuba made headlines, but not a lot of sense. The island is barely wired. Ordinary citizens pass information by thumb drives loaded up by someone lucky enough to grab a signal. The Havana government likes to control information, and so distrusts the Web. Obama has repeatedly expressed his keenness for U.S. business to help Cuba go digital, and if Havana allows that, it will signal a huge breakthrough. But something has to give, and there’s hope in Castro’s state choice of the official who will succeed him when he steps down as president in 2018: Miguel Diaz-Canel, 55, is known to be a Web enthusiast. As one former Cuban official told me with a look of wonder, “I’ve heard that the first thing he does in the morning is check his email!”

4. Castro: “Sometimes we allow ourselves to be trapped by a certain way of doing things,” Obama said in the Rose Garden on Wednesday. He was referring to Americans, but could have been talking about Cuba’s 84-year-old president. Often described as more flexible than his brother, Fidel, Raul Castro is not exactly Gumby. His efforts to shift Cuba from stagnant socialism to a market economy have been glacial and halting, more chastened by the example of “shock therapy” in the former Soviet Union than guided by the examples of Vietnam and China. Cuban officials speak of fashioning a new way forward, one that preserves the social equality that has been the government’s major accomplishment of the last five decades. But it’s far from clear that Havana has a strategy to channel the changes that ordinary people are expecting now that America is no longer an enemy.

“Of course,” Obama said, “nobody expects Cuba to be transformed overnight.” Raul Castro expects it least of all. The question is whether it will be up to him.

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