On August 31st, 2016, the first commercial flight directly from the United States to Cuba touched down on the once-forbidden island's soil. It was a tangible result of nearly three years of efforts from the Obama administration to ease 58 years of tension between the U.S. and Cuba by relaxing trade and travel restrictions, restoring diplomatic relations with Cuba and taking the island nation off the U.S. list of state sponsors of terror.
But any security of lasting reparations was short-lived. The 2016 presidential election and the death of Fidel Castro marked November with uncertainty. The former Cuban dictator's death was the emblematic end of an anti-democratic era for Cuban people, but the impending closure of the Obama era proved to have a far bigger impact – and the relationship with Cuba seemed to grow even more fragile when Donald Trump was elected as the 45th President of the United States on November 8th – only 70 days after that first commercial flight.
On November 9th, the tumult between the two countries churned again. Cuba activated their troops and began a five-day nationwide military exercise to prepare its "troops and population to counter a range of enemy action," as described by the country's Ministry of Defense. It was a sign from the Cuban government of a potential emerging diplomatic strain – a signal to the Trump administration that they would be ready, just in case. Ready for exactly what, no one could say.
In January, Trump said on Fox News that he was in favor of "opening it up" with Cuba – hinting at his own desire to foster a healthy relationship of trade, commerce and tourism between the two countries. Early in the campaign, he characterized Obama's push to open up diplomatic ties with the country as "fine." He has also actively expressed past interest in developing real estate on the island himself.
However, as president-elect, Trump pledged to "terminate" Obama's policy if Cuba continues to deny concessions to the U.S. and refuse to establish economic liberty, democracy and the freedom of expression for the Cuban people. It's Trump's way of striking a business deal in international diplomacy – and either the Cuban people or the Cuban government is going to lose. "With the amount of issues on the table, any kind of action against Cuba would be detrimental," says Tom Popper, president of Insight Cuba, a U.S.-licensed Cuban tourism operator. "Cuba doesn't possess any threat politically, economically or in any way to the U.S., so it would be an odd priority to try to curb travel and hurt that budding industry."
On January 20th, 2017 – Trump's Inauguration Day – and the days following, locals in the streets of Havana spent their time searching for answers on what Donald Trump's presidency would mean for Cuba. Peaceful coexistence of the two countries? More democratic and economic opportunities for Cubans? A reinstitution of U.S. embargo policies that isolate the island? It's clear what the Cuban people want. “I’m comfortable with my life," Alberto, a manager of several rental properties in Havana, says. "But I wish I had the freedom of expression and the freedom to vote and do what I want – to say what I want."
Donald Trump is president. Fidel Castro is dead. Raúl Castro has announced his retirement in February 2018. We are at the tipping point of a diplomatic seesaw and only President Trump's actions – not his words – will determine which way it will all go. But until then, people will live and observe and express their hopes and their worries – collectively divided.