President Obama travels to Cuba on Sunday for a historic visit meant to cement a new policy of openness toward the United States' former Cold War foe.
But the road will be bumpy, with different views on economics, politics and human rights emerging as friction points in the U.S.-Cuba relationship.
Here are five things to watch for while Obama is in Cuba.
Obama is going to talk about his vision of a Cuba with greater political freedoms and economic opportunity, but the question is how far he’ll push the envelope.
The president plans to deliver his message next Tuesday in a major speech to the Cuban people, which will be carried live on state-run television, and during a meeting with President Raúl Castro.
Obama plans to call for the Cuban people to be given the rights of free speech and free assembly, but he won’t call for Castro — who has been condemned by human rights groups for repressing his people — to step aside.
“The difference here is that, in the past because of certain U.S. policies, the message that was delivered in that regard either overtly or implicitly suggested that the U.S. was seeking to pursue regime change,” deputy national security adviser Ben Rhodes told reporters on Wednesday.
“With his message around the world, he will make very clear that that's up to the Cuban people.”
That’s in line with Obama’s strategy of using diplomatic engagement to nudge the Cubans to adopt political reforms.
But it won’t satisfy critics of his policy, who say the president’s decision to reestablish ties with Cuba rewards the Castro government for bad behavior.
The guest list
Obama also plans to meet with political dissidents while in Cuba, but the makeup of his guest list will be closely watched for any signs of interference from the Castro government.
White House press secretary Josh Earnest on Wednesday called the list “nonnegotiable,” saying Obama have the final call over who he meets with, even if it upsets the Cuban government.
But top Cuban officials have repeatedly warned Obama not to meddle in the country’s political affairs and the government has stepped up its crackdowns on dissidents in recent months.
The human-rights situation in Cuba has not improved since Obama and Castro announced their diplomatic thaw in December 2014.
Last Saturday, more than two dozen dissidents were arrested after a demonstration in Havana, including Berta Soler, a well-known activist who leads the dissident group Ladies in White.
Depending on who is on the list, the meeting will either be seen as a powerful rebuke of Castro’s restrictive policies or a missed opportunity.
Obama won’t throw out the first pitch before he takes in an exhibition baseball game between Major League Baseball’s Tampa Bay Rays and the Cuban national team.
But the president and the Cubans are hoping the baseball game could be a home run for breaking economic barriers between the two nations.
Rather than place direct pressure on Cuba to open up its political system, Obama is betting that closer economic and cultural ties will spur the Castro government to adopt reforms.
Attending the baseball game is a key part of that strategy.
Americans and Cubans share a love of baseball. Defectors from the island — such as New York Mets slugger Yoenis Céspedes and Los Angeles Dodgers outfielder Yasiel Puig — are some of the biggest stars in the game.
Behind the scenes, MLB, the Obama administration and the Castro government have discussed ways to establish a safer, more direct pathway for Cuban players to reach the majors.
The Treasury Department days before the trip loosened rules to allow Cuban citizens to legally earn a salary in the U.S. That could pave the way for an agreement with MLB for Cuban baseball players to play in the U.S. without defecting.
The Fidel factor
White House officials have stressed Obama will not meet with Raúl’s older brother, Fidel Castro, the aging leader of Cuba’s communist revolution.
An encounter with the elder Castro could cast a cloud over Obama’s visit, placing the focus on the two countries’ dark past.
Last January, the retired leader indicated he’s open to his brother’s decision to pursue normalized relations with its northern neighbor but made it clear he’s not entirely on board.
Castro, who stepped down from power in 2008, wrote in Cuba’s state-controlled newspaper that he doesn’t “trust” the U.S.
While a meeting with Fidel Castro has been ruled out, it will be interesting to see if the ailing leader makes a rare public appearance during Obama’s visit, something that would surely rankle American officials.
Breaking the embargo
The Obama administration has continued to chip away at the five-decade-old trade embargo against Cuba, enacting a litany of policy changes in the days before the president's visit.
Both sides will be looking to make even more progress on that front during the three-day visit.
In addition to the new banking rules, the U.S. dramatically loosened restrictions on travel to Cuba, eased security restrictions on cargo ships and reestablished direct mail service.
Cuba removed a 10 percent penalty on converting U.S. dollars, a gesture toward American travelers and business interests.
But the Obama administration will be pushing the Cuban government to adopt even more changes, including expanding the country’s scant Internet access and making it easier for foreign business to hire Cuban workers. Currently, Cubans must be hired through the government.
But it’s unclear if the Cubans will be willing to go along. Officials have expressed dismay the embargo remains in place, and Obama conceded in a recent interview that it won’t fall during his presidency.
Foreign Minister Bruno Rodriguez on Thursday offered no indications his government is willing to take further steps to open its economy.
"Various U.S. officials have declared in recent hours that the objective of Obama's measures is empowering the Cuban people,” he said, according to the Associated Press. “The Cuban people empowered themselves decades ago.”