Havana is warming to more open relations, too. Todd Omestead, a reporter who recently returned from the city, said “there’s tremendous enthusiasm” in Cuba about the first black president of the U.S. (“Let’s do a trade: You take Raul Castro, we’ll take Barack Obama,” someone told him.) Indeed, even Fidel Castro is reportedly rooting for Obama to succeed. Following a trip to Cuba with the Congressional Black Caucus, Rep. Laura Richardson of California said that the elder Castro “watched the election, he listened to the speeches, and he wants Barack Obama to succeed…. He sincerely wants in his lifetime to see change in the United States.”
Will the president announce any new changes to Cuban policy while in Port of Spain? That remains to be seen—we know the president likes last-minute surprises. And Carl Meacham, a senior policy adviser to Sen. Richard Lugar, who has been an outspoken advocate in Congress for lifting the embargo entirely, says “the president didn’t just talk about the fact that we need to make reforms on remittances on travel, he also said that we need to have dialogue.” But by making his first move in advance of the summit, Obama has put Cuba and its allies in the hot seat. Both Castros may say that they side with the popular new president, but, since the age of Kennedy (the last global phenom to fly Air Force One), they’ve used the U.S. embargo as a foil and a source of blame for any governmental failures. What will they do without it?
Most likely, whatever they can—and the same goes for Americans traveling to and from the troubled regime. While all the nations in Port of Spain have agreed to put Cuba on the radar this weekend, there’s no reason to think the president should spend his time courting its approval.
Dayo Olopade is Washington reporter for The Root.