President Obama and his family are traveling to Cuba. Here are some highlights of the agenda. (Jason Aldag/The Washington Post)

President Obama and his family are traveling to Cuba. Here are some highlights of the agenda. (Jason Aldag/The Washington Post)

President Obama’s arrival in Cuba on Sunday will provide the most vivid manifestation yet of the foreign policy he has championed since taking office more than seven years ago: a world in which the United States sets aside historic feuds to broker a more stable global order.

But after he leaves Tuesday afternoon, island residents will still be coping with many of the same problems that they have faced for decades: a faltering economy; a strict, one-party political system with little tolerance for dissent; and emigration of talented professionals.

[Did you or your family immigrate from Cuba? Tell us what you brought]

As Obama — with hundreds of staffers, reporters, business leaders and members of Congress in tow — works at repairing more than a half-century of enmity between the United States and the small but defiant adversary 90 miles from its shores, the administration is betting it will lead ordinary Cubans to do “extraordinary things,” in the words of Ben Rhodes, White House deputy national security adviser.

“We believe that by opening up space . . . for exchange, dialogue, connectivity, commercial opening, entrepreneurship, exchanges with civil society, that will help empower the Cuban people to live better lives,” Rhodes told reporters Wednesday. They will “be more connected not just with the United States but with the wider world,” he said.

Here are a few key moments in the diplomatic relationship between the U.S. and Cuba. (Jason Aldag/The Washington Post)

In Havana, there was palpable excitement in the streets, many of them newly paved for Obama’s arrival. In the weeks leading up to the visit, the city has had an unprecedented makeover, with government-dispatched work crews painting over worn-out building façades and patching potholes.

[Treasury eases restrictions on travel to Cuba]

An extensive shutdown of the city’s main thoroughfares is planned for the first family’s visit, adding to the aura of something big and unprecedented.

“I never thought I would see this in my lifetime,” said Manuel Pino, 44, a barber who on Friday morning recorded a video on his cellphone of Obama’s armored limousine making a practice run around the tight corners of a gas station near his house.

“The guy deserves recognition for this,” Pino said of the trip. “I think it took a lot of courage.”

[Lobbyists descend on Havana for Obama’s historic Cuba trip]

But normalization is a two-way process, and in the 15 months since Obama and Cuban President Raúl Castro announced that the countries would reestablish ties, official Cuba has been somewhat less speedy than the United States to implement changes.

Since re-establishing diplomatic ties with Cuba, the U.S. has made it easier for Americans to travel to the island nation. Here is what you need to know about changes that make it easier to visit Cuba. (Claritza Jimenez/The Washington Post)

The arrival of the first sitting U.S. president in Havana since 1928 — “without a battleship,” as Obama quipped the other day — still represents a threat to the Cuban power structure. For a country whose modern history was forged in rebellion, first against Spain and later the United States, fierce resistance remains to the idea that a more powerful nation might dictate the terms of Cuba’s path forward.

“Everything is changing in Cuba,” said Carlos Alzugaray, a retired diplomat and professor at the University of Havana. “But it’s changing according to Cuban terms” — or at least according to terms set by the communist government.

The result has been a mixed picture of progress. Long-term political prisoners now number in the low dozens — greatly reduced from years past — according to human rights activists. Opposition demonstrations, once rare events with few participants, are now regular, well-attended occurrences. But many protests are interrupted by security services, and there has been a sharp increase in short-term detentions, lasting a few hours or days.

Internet access, once reserved for the politically privileged, has increased through state establishment of public hotspots, but it remains spotty and restricted. There are a few blogs — frequently blocked by the government — and limited access to international media outlets. All authorized newspapers, radio and television on the island are government-owned.

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Most Cuban citizens who can afford it can now travel abroad relatively freely. But the number of those fleeing to the United States has soared in recent months because many fear a crackdown at home or a U.S. decision to end their unique access to permanent legal status.

State control over the economy has eased — a loosening that may have more to do with Cuba’s poor economic state than it does with any genuine political shift by the government. Roughly a quarter of Cuba’s labor force no longer works for the state, with many employed by a private sector that is prospering despite strict government controls.

American investment is still prohibited by the ongoing U.S. embargo, and businesses in countries without such restrictions have been reluctant to put money into Cuba. Many in the steady stream of U.S. business representatives who have made their way to Cuba since Obama began lifting restrictions on exports to certain sectors have been disappointed by Cuba’s lack of eagerness to deal.

“Change in Cuba in inexorable. But there’s no Arab Spring in Cuba. It’s not 1989 Prague,” said Julia Sweig, a senior research fellow at the University of Texas’s Lyndon B. Johnson School of Foreign Affairs, who has been visiting Cuba since 1984.

When it comes to the public debate in Cuba, she added, “there’s far less fear and there’s less censorship,” but major political reforms remain unrealized.

Some speculate that major changes will take place after February 2018, when Raúl Castro is to step down; others predict that the political structure will remain in place indefinitely under new leadership. But it is clear that the Cuban president is hoping to be the bridge between the strict communist society his brother Fidel’s revolution brought about and the hybrid it has become.

[Obama’s goal for Cuba trip: Become a source of support]

“The Cuban Revolution is his brother’s legacy, and what happens after . . . is his,” said Dan Restrepo, Obama’s top Latin America adviser in his first term and now a senior fellow at the Center for American Progress.

“His calculus is he thinks he can control the genie,” Restrepo said of Raúl Castro.

Obama’s decision to visit Havana has been sharply criticized by opponents of normalization, especially within the Republican Party. Donald Trump, the only GOP presidential candidate to offer support, has said he was “fine” with rapprochement, although he says he could have forged a “better deal” with Cuba.

House Speaker Paul D. Ryan (R-Wis.) denounced the trip in a statement Thursday. Cuba’s government, he said, remains “a regime that provides safe harbor to terrorists and fugitives.” Ryan added that he did not think Obama “will bring up the need for reform during his visit,” even though the White House has pledged to do so.

“Instead, he is set to announce new commercial deals . . . that will legitimize and strengthen the communist government,” Ryan said.

But American and Cuban officials are betting that there is enough support in both their countries to sustain the policy shift, even if the next president has a different philosophy.

Yanetsi Azahares, 28, owner of the Gelato House, a high-end ice cream cafe on the Havana waterfront, said she was already thinking about the visit’s impact on Cuban tourism.

“I think a lot of Americans are going to see that he’s welcome here and realize they will be welcome, too,” she said.

Nick Miroff in Havana contributed to this report.

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