When President Barack Obama hits Port of Spain, Trinidad and Tobago this weekend for the Fifth Summit of the Americas, all of the democratically elected governments of the Western Hemisphere will be there to talk trade, recession and security issues. Well, almost all. The single outcast: Cuba, the undemocratic island nation on which the U.S. has maintained a diplomatic and trade embargo since 1962. Though Cuba will not be present at the talks, it’s sure to be a hot topic at the summit and in bilateral sessions between the U.S. and South- and Central-American leaders.

For 50 years, the U.S. has essentially tried to pretend Cuba doesn’t exist, but this administration won’t have that option: Obama dragged Cuba and its aging former president, Fidel Castro, back into the spotlight this week. The announcement that travel and remittance restrictions will be lifted for Cuban Americans was “the first ever such bilingual rollout in the White House, from the White House podium,” according to Denis McDonough, a national security communications adviser to the president, who also said Obama has made “a very consequential set of policy changes” regarding Cuba. Americans who don’t have Cuban relatives won’t feel a thing—but Team Obama clearly hopes they can file this one under “change you can believe in.” Many Latin American nations, however, are not yet ready to let the backslapping begin.

Ever since President John Kennedy placed the trade and travel embargo on Castro’s regime, U.S.-Cuban relations have been a proxy for other political concerns—the Cold War struggle against Communism, American global authority and tangled domestic politics within the swing state of Florida, where many Cuban Americans are concentrated. Today, leaders from large nations like Argentina, Mexico and Brazil view the cause of Cuban openness as a proxy for their own relationship with the United States. The dozens of nations in the continent that do recognize Cuba reportedly resent a “Cubanization” of regional policy—and “have made Cuba the litmus test for judging Washington’s policy toward Latin America,” said Julia Sweig, director of Latin Studies at the Council on Foreign Relations, at a conference this week. The White House acknowledged as much the same day of its Cuba announcement: The U.S. has “neglected its relationships in this part of the world,” said Ambassador Jeffrey Davidow, director of American presence at the summit. “Whether one agrees with that perception or not, it certainly is a very strongly felt perception.”

The U.S. delegation would like to focus the summit on three main subject areas: economic stability, energy action and public safety—the former because some 50 million people could drift back under the poverty line after the gains of the last five to six years, and the latter as violence related to drug trafficking has exploded along the U.S.-Mexican border in 2009. (The Department of Homeland Security recently appointed Alan Bersin as a “border czar” to help confront that problem.) The White House has said it will consider appointing a regional diplomat to handle Latin American issues, similar to the kind sent to handle climate change, the Middle East and Israel/Palestine.

But, both because of the new shift in policy and the expectations of summit partners, Cuba may still have an oversized presence in deliberations—a presence it no longer really deserves.

Despite today’s heated rhetoric surrounding Cuban human rights abuses, crackdowns on speech, retrograde labor practices or presidential posturing, the island nation has barely been of strategic significance to the United States since the founding fathers thought they would, after annexing Florida, turn Cuba into the next American state. With only 11 million people, it’s a fraction of the size of Brazil, which is hankering to join the UN Security Council, and the same size as Bolivia, which sits on important lithium deposits to be used in next-generation battery technology. It has no weapons, and no real enemies—besides the United States.

Moreover, “unilateral sanctions are bad policy in almost every situation,” says William Reinsch, president of the National Foreign Trade Council. And Cuba has been a particularly ridiculous case in point. In addition to being hypocritical (the U.S. promotes free trade and is supposedly anti-terror; yet we don’t trade with Cuba, and former Cuban radicals live in the United States), the embargo is widely recognized to have been a failure. Both Castro and his brother, Raul, after all, are still running the country. And this stubbornness has enervated American allies in the Caribbean—as Obama may soon find out.

So there is a large incentive to junk the failed policy toward Cuba—not because doing so would change anything about the 21st century world order, but because it presents an easy opportunity for Obama to signal that he’s a real change agent. Cubans have seen almost a dozen American presidents come and go with no shift in treatment—though polling suggests U.S. public opinion toward the communist state has softened in recent years.

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.