As Trump sets sights on Cuba, I’m reminded of how different things used to be

Against the backdrop of military operations in Venezuela and Iran, the White House has cut off Cuba’s oil supplies and threatened a “friendly takeover” of the Communist-run island.

US President Donald Trump has suggested that the country is his next target, saying: “Whether I liberate it, whether I take it over, I think I can do whatever I want with it. They’re a very weak nation right now.” Oil shortage is bringing Cuba’s economy to the brink. But I found myself thinking about a time, not so long ago, when it seemed as if the two countries would normalize relations after decades of hostility.

I first arrived in Havana in March 2012 to cover the visit of Pope Benedict XVI. The airport was small. I had to repeatedly explain to the immigration officers that we were there as journalists, we had permission and everything had already been cleared. I’m grateful that my team spoke Spanish to help with this process.

Parts of the city seemed strangely familiar to images I’d seen of faded pastel buildings and old American cars that were somehow still running on parts that were cobbled together.

Cuba and the United States have been geopolitical enemies for more than 50 years. Cuba became communist when the 1959 revolution brought Fidel Castro to power and the island nation, just 90 miles from Florida, strengthened its ties with the Soviet Union. In response to the increasing US embargo the Cuban government seized US property and US-owned businesses. In response, President John F. Kennedy formalized a complete ban in 1962. Supplies of food, fuel and consumer goods soon became scarce.

But while living there I felt that something was beginning to change.

Between 2012 and 2016, I made 10 trips, doing field production for CNBC with international correspondent Michelle Caruso-Cabrera. It seems that almost every trip is associated with some significant event – ​​moments that feel like they may mark a turning point. But by the end, that pace suddenly felt uncertain.

On my first visit, Havana was trying to look ready for a Pope. Freshly painted sections of the Malecón, the route along which the Pope was expected to visit, is still drying in places. In a country shaped by decades of communism, their presence felt like much more than a religious event. It felt like a signal, subtle but unmistakable, that Cuba might open up.

After that, things started moving forward rapidly.

Less than a year later, the government invited a small group of journalists, including us, to take a closer look at what it called “reforms.” We talked to central bank governors, and small business owners who were trying to navigate a system that was changing, but not all at once.

We strayed from the official itinerary and headed to Hershey, Cuba, a town that Milton Hershey built in the early 20th century to secure sugar for his chocolate business. It was one of many reminders of the American past before the Cuban Revolution. A former Coca-Cola factory was renovated by the state. The country’s telecommunications company was located in a building belonging to Western Union. The Woolworth’s store became the local discount store.

In July 2015, President Barack Obama announced the restoration of diplomatic relations. We quickly moved out of New York to Miami, then on a charter flight to Havana. There was a real atmosphere of excitement on the field. But it was not unsafe. People were hopeful, but cautious.

A month later, the US Embassy reopened for the first time in more than 50 years. I watched the flag rise from the balcony of a crumbling apartment building across the street. Especially for young Cubans, this felt like a turning point: more opportunities, more access, more choices seemed within reach.

Obama’s visit the following March heightened that sentiment. Travel restrictions for Americans were eased and limited business resumed. The ban still remained in place as written in US law, but was relaxed slightly.

That week brought a Rolling Stones concert and a Major League Baseball game, the first on the island in years.

Still there was restraint. Cubans had learned not to get ahead of themselves. For many, the optimism came with the reminder of how quickly it could end. After all, not everyone believed that the United States should reopen relations with the country. Many argued that normalizing relations would reward the communist government without implementing meaningful reforms.

Still, things were changing. In 2016, Carnival Cruise Line, under its Fathom brand, docked in Havana, the first American cruise ship to visit the island since 1978. By November, JetBlue was running direct flights from New York. For a while, it seemed as if the odds were coming down in real time.

Reporting there was never easy. Permits may be canceled without warning. Phones rarely worked. Wi-fi was difficult to find. Restaurants offer long menus, but when you ask, you are often told that only rice and beans are available. I pass by beautiful buildings, but once inside I find them hollow, crumbling, little more than dust and debris.

And yet, on each visit, you could see small signs that change was afoot. Family-run restaurants started opening in people’s homes. Airbnb listings began to proliferate. It wasn’t dramatic, but it was there.

My last trip was in November 2016, just after Fidel Castro’s death, to cover his funeral. He had handed over power to his brother Raul years earlier, but the death of the man who symbolized the revolution was a huge moment.

This time, Havana was quiet.

The music stopped. The wine disappeared. The city entered a formal mourning period. People stood in long queues to sign condolence books.

From the outside, it seemed like the obvious end. Inside Cuba, it didn’t seem so easy.

Standing there, it was hard not to feel that the energy of the previous years was waning. The same questions kept coming back. what happens now? What will happen to the reforms? Of relations with the United States?

When I walked out there for the last time, I realized I had witnessed something rare, a brief period of time when history seemed to accelerate, when long-held patterns loosened up, even if just a little, and for a moment the future felt wide open.

In the years since, much of this momentum has slowed, and in some cases reversed. The US withdrew embassy personnel, new travel limits were implemented in November 2017, and the flow of US visitors decreased. The opening that once felt within reach has given way to more familiar tensions, which are flaring as if the change I saw never happened.

History doesn’t always come with a clear beginning or a clear end. In Cuba, the tendency is to circle back in on itself.

What will happen next between these two neighbors is still unwritten.