Image: Cubans read the newspaper
Sven Creutzmann/Mambo Photo  /  Getty Images
A newspaper vendor sells the Granma, Cuba's main newspaper and official organ of the Communist Party on Wednesday in Santiago, Cuba. Cuba celebrated the 50th anniversary of the Cuban Revolution on Thursday.
By Chief foreign affairs correspondent
NBC News
updated 1/1/2009 5:48:25 PM ET 2009-01-01T22:48:25

WASHINGTON — As Cuba marks the 50th anniversary of its Communist revolution this week, it is looking to Washington and wondering how Barack Obama, the 11th U.S. president to face the Castro regime, will change the stormy relationship with Havana.

On Jan. 1, 1959, revolutionaries led by Fidel Castro overthrew the U.S.-backed government of President Fulgencio Batista.

Within years, President John F. Kennedy imposed the economic embargo that has been the framework for the U.S. relationship with Cuba ever since.

Cuba has survived for half a century by relying on its friends — first, the Soviet Union, now Venezuela, and by blaming the U.S. embargo for its ills. U.S. presidents in both political parties have played into the Cuban narrative.

Today, Havana is looking north for any hint of an overture from the incoming Obama administration, and south toward Venezuela, whose billions in aid during the years of high oil prices — along with easy credit from Russia, Iran and China — have helped sustain the island's beleaguered economy.

But how much longer can Cuba rely on its allies for financial support as oil prices tumble?

Now a new American president's ideas for the relationship will be tested. What happens next will depend on Obama — and on the agility and intentions of his counterpart, thirty years his senior, Cuban President Raul Castro.

Overtures from a new Castro leader?
While 82-year-old Fidel Castro still writes on any and all subjects for the Communist Party daily, his 77-year-old brother Raul is clearly in charge. Until now, Raul has not made any bold moves.

But recently, he signaled interest in a dialogue with the U.S., suggesting the possibility of a prisoner exchange — focusing on five Cubans viewed by Havana as heroes, but imprisoned in the U.S. as spies. For its part, Washington is keenly interested in any sign that Cuba will release scores of political prisoners, writers and other dissidents jailed by Fidel Castro during a crackdown nearly six years ago.

As with all diplomacy, progress toward an easing of tensions will require timing, reciprocity — and mutual deniability. The Cubans are insisting on negotiations with no preconditions. The U.S. side has long demanded action on human rights before any easing of trade or travel restrictions.

The stalemate has suffered, or benefited, depending on your point of view, from not-so benign neglect: While the embargo is central to all policy discussions in Cuba, since 9/11 and the wars in Iraq and Afghanistan, Cuba has become, at most, a minor irritant to Bush policymakers.

Cuba looking for ‘change,’ too
Over the past decade, I've visited Cuba frequently as a journalist — one of the few professions still permitted under the Bush administration's tightened restrictions to travel freely to the island.

Even during periods of extreme strain in the relationship, such as the protests over the case of Elian Gonzalez in 1999, I've found that average Cubans are keenly interested in learning everything they can about the United States. Most want to clear away the tangled underbrush of misunderstandings that have grown between the two nations over the course of a half-century. That curiosity about the United States has only increased as more and more Cubans gain access to the Internet through bootlegged technology. 

But to many on both sides, it seems as though every step forward — increased tourism years ago, grain deals between Midwestern farmers and Cuban agriculture officials, various cultural exchanges — was met with some deliberate or unintended obstacle put forward by one or both of the two governments.

This despite the fact that observers on the island and in the U.S. believe that much could be shared between the neighbors if some level of dialogue were restored. Such progress could include, but not be limited to, potentially productive agreements on migration, drug interdiction, health care, and hurricane relief.

After a series of devastating hurricanes and the fallout from the deepening global recession, Cuba would obviously benefit greatly from trade with its closest neighbor.

Cuban officials insist they want to engage, and are only awaiting a signal from the new American president if he attends, as is expected, a scheduled Latin American summit in Trinidad in April.

Will an Obama administration change course?
Will Obama revisit Cuban policy so early in his new administration? Arguably, he faces many more critical challenges in Iraq, Afghanistan, Pakistan, Iran, and now Gaza.

But for the United States, the embargo has become a double-edged sword. At the United Nations in October, the General Assembly voted once again for a resolution urging the United States to repeal its trade embargo against Cuba, as it has for 17 years in a row.

The tally in favor of Havana was overwhelming, 185 countries to 3. Only Israel and Palau joined the U.S. in supporting the 47-year-old embargo. Obama's transition team is being told that easing the Cuba policy would be a quick way to win friends in this hemisphere.

And the political calculus in the U.S. is no longer predictable. In Florida, for instance, younger Cuban-Americans are less resistant than their parents and grandparents to the idea of restored relations. Even a slight easing of Bush administration restrictions on travel and remittances to Cuba would be popular among many Cuban-Americans. 

Nothing will be done in Havana or Washington without intense focus on the political ramifications. Obama's party now sees a political opening in Florida in 2010, with the announced retirement of Senator Mel Martinez. In vying for the open seat, Democrats could even be facing a popular former governor named Bush — Jeb Bush — who is strongly anti-Castro, and potentially the GOP's best candidate.

Watching how their governments handle the delicate dance over future relations will be Cuban-Americans, who have had an exaggerated influence over U.S. policy in the past, as well as the Cubans, who have been waiting and waiting — for 50 years.

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