Fidel Castro votes for the new head of the Communist Party from his home on April 18, 2011.
Obama to meet with Castro?
02:30 - Source: CNN
Washington CNN  — 

Emboldened after striking a preliminary nuclear deal with Iran, President Barack Obama heads to a gathering of South and Central American leaders this week prepared to test his doctrine of engaging sworn U.S. enemies, this time Cuba.

After a brief stopover in Jamaica Wednesday to meet with Caribbean leaders, Obama heads to the Summit of the Americas in Panama, where officials say he plans to “interact” with Cuba’s President Raul Castro following his decision to improve relations between the two countries.

Castro is attending the gathering for the first time after Cuba was drummed out of the Organization of American States more than half a century ago.

Unlike past summits, when the United States’ stance on Cuba was a major point of contention, White House officials expect the realignment to be hailed at the two-day event, during which Obama also plans to tour the Panama Canal and seek to ramp up commerce with Latin America.

Obama and Castro aren’t scheduled to meet formally this week, but Obama’s aides have hinted at a set agenda for whatever conversation emerges when they encounter one another on the sidelines of the conference.

RELATED: Obama, Cuban president to ‘interact’ at Panama meeting

That includes finalizing plans to reopen embassies in Havana and Washington and continuing to bolster commercial ties between the neighbors, which began to form after Obama lifted long-standing restrictions on commerce and travel last year.

It’s also likely to center on Obama’s decision to remove Cuba from the U.S. list of state sponsors of terror, a commitment officials say he’ll make this week after receiving a recommendation on the matter from the State Department. The State Department recommended removing Cuba from the list. Obama said Thursday he was aware of the decision but hadn’t been formally presented with the recommendation and therefore wouldn’t comment further.

Cuba has raised the designation as a major objection in its talks with U.S. officials regarding normalizing relations between the two Cold War adversaries.

Obama, in an interview with NPR this week, signaled his predilection for removing Cuba’s terror status.

“The criteria is very straightforward: ‘Is this particular country considered a state sponsor of terrorism,’ not, ‘do we agree with them on everything,’” he said. “Those standards, those criteria are the ones that are going to be measured against the current activities of the Cuban government.”

Obama and Castro, who spoke on the phone after the U.S. announced in December it was seeking to thaw frozen relations between the two countries, last interacted in person at Nelson Mandela’s funeral in 2013 when they shook hands spontaneously.

Analysts predict their interaction this time around will be more substantive — though not yet exactly chummy.

“I don’t think there will be lots of hugs and kisses,” said Ted Piccone, a senior fellow at the Brookings Institution Latin America Initiative. “I think it will be serious and it will be respectful and measured, and they will reinforce the larger theme…that dialogue and engagement is better for constructive relations than negative sanctions.”

Since the handshake in South Africa, officials in both countries have worked to ease the decades of U.S.-Cuba enmity, culminating in the announcement late last year that diplomatic relations were reopening. Some in Cuba have lamented the pace of the thaw, though Obama’s aides argue the high stakes mandate careful deliberation.

RELATED: Fidel Castro, in rare public appearance, is ‘full of vitality’

“When you have two countries that haven’t really spoken to each other like this in over 50 years, you have a lot of issues to work through,” Obama’s Deputy National Security Adviser Ben Rhodes said, noting that talks to reopen embassies weren’t likely to be complete by this week’s summit — originally an administration goal.

Officials insist they’re otherwise pleased at the progress toward reestablishing diplomatic ties, which the White House argues has helped improve relations with other countries in the region.

“We felt it was long overdue and takes a huge irritant out of our policy in Latin America and the Caribbean,” said Roberta Jacobson, the Assistant Secretary of State for Western Hemisphere Affairs who’s led talks with Cuba reestablishing diplomatic ties.

The summit meetings Friday and Saturday will mark the first time Cuba participates in the conference, which takes place every three years. At the two Obama previously attended, in Trinidad and Colombia, reception toward the U.S. delegation was icy.

RELATED: Cuba talks continue, terror list a sticking point

“It was really painful to see how isolated (Obama) was, what a punching bag he was. I think that atmosphere will be very different now three years later,” said Richard Feinberg, who handled inter-American affairs in President Clinton’s National Security Council and is now a professor of international political economy at the University of California, San Diego.

While Cuba may help smooth U.S. overtures to Latin America, a more aggressive stance against Venezuela could prove troublesome for Obama. In March the White House announced it was expanding sanctions on certain Venezuelan officials for human rights abuses following political unrest.

The country’s president Nicolas Maduro planned to present Obama with petitions signed by millions of his countrymen protesting the executive order, which declared Venezuela a “national security threat.”

U.S. officials insist the language in the sanctions order was pro forma and that Venezuela doesn’t pose a threat to U.S. security. But they acknowledge agitation over the sanctions in the region will arise during the summit.

“It will certainly be an issue,” Rhodes said. “But again, what we’ll be making clear here is that we stand up for a set of universal values everywhere.”

Like negotiating with Iran, renewing ties with Cuba sparked outrage from some lawmakers, who argued it was a misguided effort to engage a corrupt government. But Obama, in an interview with the New York Times this week, argued there were few risks of pursing a better relationship with Cuba.

“For us to test the possibility that engagement leads to a better outcome for the Cuban people, there aren’t that many risks for us,” he said. “It’s a tiny little country. It’s not one that threatens our core security interests, and so for us to test the proposition and if it turns out that it doesn’t lead to better outcomes, we can adjust our policies.”

RELATED: White House sanctions Venezuela for rights abuses, corruption

CNN’s Elise Labott contributed to this report.