A recent view of downtown Havana. (Photo: Alexandre Meneghini/Reuters)

For nearly 50 years, the United States tried various ways to end the Castro regime that rules Cuba. The disastrous 1961 Bay of Pigs invasion led to the convoluted scenarios laid out in “Operation Mongoose,” including plots to poison Fidel with a cigar, or a wet suit, or hiring organized crime figures to kill him. Later, the crippling U.S. economic embargo aimed to convince the island’s population to rise up and overthrow the Soviet ally just 90 miles off Florida’s shores.

Both the use of force and economic pressure failed to bring about the desired result — while Castro boasted of surviving CIA hit jobs and blamed poor living conditions in socialist Cuba on the U.S. The bearded revolutionary outlasted U.S. president after U.S. president, and his government even survived the collapse of the Soviet Union, which deprived Havana of aid from Moscow. The end of the Cold War also set the stage for American allies, like Mexico, Canada and France, to carve out lucrative niches in Cuba’s tourism industry, leaving the United States isolated.

When Pres. Barack Obama arrives in Havana on Sunday, it will be at the head of what amounts to a different kind of U.S. invasion. There will be air power: Airlines clamoring to be able to run direct flights to Cuba. There will be naval power: Cruise lines launching routes to Cuba. Marriott, looking to become the largest hotel chain in the world through a merger with Starwood, wants to establish a beachhead. And the president has potentially enlisted tens of thousands of infantry by recently loosening restrictions on Americans traveling to Cuba to such an extent that, while a ban on simple tourism remains on the books, it’s easy, in practice, to travel there to take in the sights.

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“Our central premise,” Obama told Yahoo News in an interview in December, is that if “they are suddenly exposed to the world, opened to America and our information and our culture and our visitors and our businesses, invariably they’re going to change.”

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The president will arrive in Cuba on Sunday evening with first lady Michelle Obama and their daughters, Malia and Sasha, for a whirlwind visit — a little less than 48 hours in Havana.



“I look forward to being the first U.S. president to visit Cuba in nearly 90 years — without a battleship accompanying me,” Obama said recently, referring to Calvin Coolidge’s 1928 trip aboard the USS Texas.

The historic trip will highlight his efforts to make his policy changes irreversible, even if a Republican retakes the White House in November’s elections.

Workers repair the street in front of the Capitolio in Havana, March 14, 2016. (Photo: Ramon Espinosa/AP)

The president will meet with his Cuban counterpart, Raúl Castro, but not with Fidel, who used to delight in delivering roaring seven-hour speeches, but has been seen in public less and less since handing his brother the reins in 2008. He’ll take in some of the sights in Havana, and attend an exhibition baseball game pitting the Tampa Bay Rays against Cuba’s national team. There will be a state dinner. He will also deliver a speech about steps that must still be taken to further improve relations, a message that White House aides say will be broadcast on Cuban television. He will meet with Raúl Castro at the Palacio de la Revolución, the seat of government, and criticize his regime’s human rights record both there and in a meeting with hand-picked dissidents.

“We’re trying a new approach,” White House press secretary Josh Earnest told reporters Friday. “Our approach now is that the president of the United States is going to get on Air Force One, he is going to fly to Havana, Cuba, and he is going to sit down with the leader of Cuba and say, ‘You need to do a better job of protecting the human rights of your people.’”



White House officials have taken pains not to predict a speedy democratic revolution in Cuba. Instead, they say, American investment, tourism and trade will raise Cuba’s standard of living, while even modestly expanded communications, including Internet access, will help Cubans engage with the wider world.

“We know that change won’t come to Cuba overnight,” White House National Security Adviser Susan Rice said Thursday. “We believe that engagement — including greater trade, travel and ties between Americans and Cubans — is the best way to help create opportunity and spur progress for the Cuban people. “

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Obama is not expected to nominate an ambassador to Cuba on the trip. The current top U.S. diplomat there, Jeffrey DeLaurentis, is a widely respected career State Department staffer. Naming an ambassador, Obama aides say privately, would pack too many risks and too few rewards. It would not alter the day-to-day diplomatic work, while embroiling the White House in yet another battle with Republicans in Congress. And failure to win confirmation would deal a sharp symbolic blow to Obama’s policy.

Obama still seeks ambitious changes on both sides of the Florida Straits. In the United States, he wants Congress to lift the embargo. In Cuba, he wants the government to take its own big steps, like allowing American businesses to hire directly, bypassing the patronage system that helps Castro hold on to power.

“A real game changer would be a situation in which you have a direct employer-employee relationship,” Obama told Yahoo News in December.

Cuba’s government, though hungry for foreign investment, has not eagerly embraced the idea of political change. The official Communist Party newspaper, Granma, recently editorialized that the country would retain its “unconditional commitment to its revolutionary and anti-imperialist ideals,” and emphasized there remains “a long, difficult road” to a full restoration of relations.



A man fishes as commuters take a ferry to Havana, March 2016. (Photo: Ramon Espinosa/AP)

Obama himself told Yahoo News last year that Raúl Castro is looking to harness the benefits of American investments without embracing democratic reforms.

“What he probably wants to pull off is a transformation of the economic system to make it more productive and more efficient and raise standards of living — without letting go of the political reins,” the president said.

That’s what happened in Vietnam, the country Obama aides often mention in conversations about Cuba.



It’s a cautionary tale. When Bill Clinton announced plans to normalize relations in July 1995, he drew a straight line connecting American investment and tourism to improved human rights.

“I believe normalization and increased contact between Americans and Vietnamese will advance the cause of freedom in Vietnam, just as it did in Eastern Europe and the former Soviet Union,” he said.

Twenty years later, the State Department’s annual human rights report about Vietnam deplored “severe government restrictions of citizens’ political rights, particularly their right to change their government through free and fair elections; limits on citizens’ civil liberties, including freedom of assembly and expression; and inadequate protection of citizens’ due process rights, including protection against arbitrary detention.”

Still, Obama told Yahoo News last year, “Raúl Castro recognizes the need for change,” and wants to “help usher in those changes before he and his brother are gone,” leaving a successor without the clout to transform Cuba either politically or economically.

After all, Obama said, “nobody’s got better street cred when it comes to, you know, Cuban revolutionary zeal than one of the original revolutionaries.”