- The last visit to Cuba by a sitting US president was in 1928
- That was President Calvin Coolidge, who visited aboard a battleship while the island was under American control
- Barack Obama is expected to meet Raul Castro, but not Fidel, who was the target of CIA assassination attempts
- The future of Guantanamo Bay may be a sticking point in the normalisation of relations between the two countries
It started with a handshake between US President Barack Obama and his Cuban counterpart Raul Castro in South Africa in 2013, then again in Panama two years later. This simple gesture snowballed into a number of milestones that marked the end of hostilities - spanning 11 American presidencies - between the two countries.
But Obama will soon crown these preliminary interactions with a visit no other US president has taken while in office in almost nine decades: a trip to Cuba. The administration hopes that Obama's visit to the island - during his last year in the White House will be legacy-making.
The visit, the administration says, is intended to cement all the steps taken to normalise relations with Cuba after five decades of estrangement. But some say it's much more than that: it's also an admission that the decades-long US policy towards the island nation has not worked.
"It is a recognition of the validity of the Cuban revolution, and an exercise in respect," said Peter Kornbluh, who directs the Cuba Documentation Project at the National Security Archive in Washington DC. "It will be Obama's 'Nixon to China' moment, and he will go down as the president who ended the Cold War in the Caribbean once and for all."
In 1972, President Richard Nixon visited Beijing, ending decades of hostility with China. Like Obama's expected trip to Cuba, Nixon's was hugely controversial, but it cemented Washington's detente with the communist state, leaving little wiggle room for any succeeding US president to deviate from that policy.
"This trip is intended to accelerate momentum for engagement and normalisation of relations, and to consolidate and fortify this policy and make it irreversible for any president who may want to change it," Kornbluh told Al Jazeera.
Calvin Coolidge v Barack Obama
On his two-day trip to Havana, which begins on March 21, Obama is expected to meet Raul Castro as well as Cuban entrepreneurs and community activists, to announce new steps to bolster bilateral ties, attend a Major League Baseball game, and address Cubans directly. He will be joined by First Lady Michelle Obama, Minority Leader Nancy Pelosi and 16 other House Democrats.
He is not expected to visit Fidel Castro, the leader of the 1959 Cuban revolution who was a target for numerous assassination attempts by the CIA, and there is some speculation that he will meet dissidents on the island privately.
"Where he speaks and to whom will be interesting to see," said Van Gosse, who teaches history at Franklin & Marshall College in Pennsylvania. "He is going to walk a careful line between what the only other US president did when he visited Cuba, which was at the time a protectorate of the US, and now, with it being a sovereign nation."
Things were very different the last time a sitting US president went to Cuba. When Calvin Coolidge visited Havana in 1928 aboard a battleship, the island was under American control. The relationship was defined by the Platt Amendment, which in exchange for the withdrawal of US troops - who remained after the Spanish-American War - effectively turned Cuba into a neo-colony.
"Coolidge's visit enacted that relationship of that suppliant ostentatious subordination," said Gosse, the author of Where the Boys Are: Cuba, Cold War America and the Making of a New Left. "Coolidge also met Gerardo Machado, the dictator who was stabilising Cuba on behalf of American business interests. The president was saying that Cuban independence was a gift from the US. Of course, the Cuban revolution said otherwise."
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The Obama administration's new policy to engage with Cuba was years in the making. In 2009, Washington lifted travel and spending restrictions for Americans with family on the island. More barriers between Havana and Washington came down in mid-2013 after secret talks brokered by Pope Francis eventually led to a prisoner exchange.
But it was the 2014 announcement that the US and Cuba would begin a new era of relations that heralded many milestones. "Today, the United States of America is changing its relationship with the people of Cuba. In the most significant changes in our policy in more than 50 years, we will end an outdated approach," Obama said at the time.
And over the course of a year, a relationship that looked like it would never change, did, and with it the last vestiges of the Cold War were slowly dismantled.
In January 2015, the US further eased restrictions on travel to Cuba, and in the spring of that same year, the island was finally removed from the the list of state sponsors of terrorism - 23 years after being consigned to it by President Ronald Reagan.
A turning point in diplomacy came in July 2015, when Washington said it would reopen its embassy in Havana for the first time since 1961. Last month, an aviation agreement was struck that would restore direct flights between the US and Cuba "as soon as possible". And now the administration has announced that Americans can make trips to the island for educational purposes on their own instead of on group tours - as was previously required. The new rules also allow easier use of the American dollar in transactions with Cuba.
US policy on Cuba riles critics
But the White House is facing stiff opposition from hardline anti-Castro politicians on Capitol Hill, and Obama's trip became election campaign fodder for some of the candidates, who have criticised the president's trip as a reward to a repressive regime.
Human rights groups also want Obama to make the issue of dissident crackdowns in Cuba central to the dialogue with authorities during his visit.
"In November [of 2015], there were 1,400 politically motivated detentions in Cuba, which is the highest number in many years," said Marselha Goncalves Margerin, an advocacy director for the Americas at Amnesty International USA. "The harassment of government critics, including journalists and human rights activists, and arbitrary arrests and detentions continue."
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The White House has acknowledged that differences remain between the two countries over human rights issues, but, according to Ben Rhodes, Obama's deputy national security adviser and a key architect of the president's Cuba policy, engaging the former adversary is beneficial for both democracy and US economic interests.
"We believe that not going and isolating Cuba doesn't serve to advance those issues; that we will be in a better position to support human rights and to support a better life for the Cuban people by engaging them and raising these issues directly," Rhodes said.
No other US president has veered off the beaten path drawn by Cuban exiles, who have traditionally been staunchly opposed to any softening of American policy towards the island.
"If you ask many Cubans in Miami what they think about this trip, they will tell you this is the biggest betrayal since the Bay of Pigs," said Miguel De La Torre, a professor of social ethics and Latino studies at the Iliff School of Theology, in Colorado.
"But if we base our foreign policy on other countries' human rights issues, then we would not have any relations with Saudi, Israel or others," the Cuban-born De La Torre told Al Jazeera. "We also have some human rights issues in our country. To use that argument towards Cuba alone is disingenuous."
'Relations won't be fully normal'
A 2015 poll found that 73 percent of Americans approved of the US re-establishing diplomatic relations with Cuba. Support for renewed ties with the once estranged country even increased from previous years across nearly all partisan groups, with 56 percent of Republicans - traditionally more opposed to engaging Cuba - saying they approve of the US move.
The Pew survey found that 72 percent favoured the US ending its trade embargo against Cuba - one of two thorny issues that linger amid the warming relations - which only Congress can lift; a highly unlikely task with fierce Republican opposition.
"It's hard to imagine the embargo being lifted in a presidential year," said Tomas Bilbao, a policy advisory board member of Engage Cuba, a coalition of groups pushing for normalisation.
"But there is overwhelming consensus in the US that the policies of the past half-century have failed, and that we should try something different," Bilbao told Al Jazeera. "We are in the best condition, and momentum is on our side, to get the embargo lifted, but it will depend on the outcome of the elections."
At the heart of the embargo - in place since President John F Kennedy was in office - is compensation for US companies and citizens whose properties were confiscated after the Cuban revolution, amounting to about $1.9bn (worth an estimated $8bn with interest). The Cuban government is also claiming damages of up to $121bn, which it says five decades of American economic sanctions have cost the island.
Then there's the issue of the land housing the navy base at Guantanamo Bay - occupied by the US for more than a century - which Havana wants back. Washington says this issue is not up for debate, but some believe that it's inevitable that the US will relent.
"The Cubans have made it clear that relations won't be fully normal if the US continues to occupy the most beautiful part of the island," Kornbluh said. "All issues are up for negotiation. And I would guess that in the next decade, Guantanamo will be given back. But it all depends on whether you have a majority in the Senate, and the House changes, and who's the next president."
Source: Al Jazeera