As Trump eyes Cuba, I remember me how different things used to be

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

US President Donald Trump hinted that the country was his next target, saying, “Whether I release it or take it, I think I can do whatever I want with it. They are a very weakened nation right now.” Oil shortages are pushing the Cuban economy to the brink. But I found myself thinking about a time, not so long ago, when the two countries appeared likely to normalize relations after decades of hostility.

Havana was first visited by Pope Benedict XVI. I landed in March 2012 to cover Benedict’s visit. The airport was small. I had to explain many times to the immigration authorities that we were there as journalists, we had permission and everything had been arranged in advance. I was grateful that my team spoke Spanish to help with the process.

Parts of the city looked oddly familiar from the images I’d seen of faded pastel buildings and old American cars that somehow still ran on patchwork parts.

Cuba and the United States were 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. The Cuban government seized US property and American-owned businesses in response to the increased US embargo. In response, President John F. Kennedy formalized the full embargo in 1962. Supplies of food, fuel, and consumer goods quickly became scarce.

But while I was there, I felt things starting to change.

Between 2012 and 2016, I made 10 trips to field production for CNBC with international correspondent Michelle Caruso-Cabrera. Almost every visit seemed to coincide with something important; Moments that feel like they could be turning points. But eventually, that momentum suddenly became uncertain.

On my first visit Havana was trying to look ready for a pope. Parts of the Malecón were covered in fresh paint and were still drying in places along the route the pope was expected to travel. In a country shaped by communism for decades, his presence seemed like more than a religious event. This felt like a subtle but unmistakable signal that Cuba could open up.

Things started to move quickly after that.

Less than a year later, the government invited a small group of journalists, including us, to see what it called “reforms” up close. We spoke with the governor of the central bank and small business owners trying to navigate a system that’s changing, though not all at once.

We veered away from the official route and headed towards the Cuban town of Hershey, which Milton Hershey built in the early 20th century to supply sugar for his chocolate business. This was one of many reminders of Cuba’s pre-revolutionary American past. An old Coca-Cola factory was redesigned by the government. A Western Union building housed the country’s telecom company. Woolworth’s had become a local discount store.

In July 2015, President Barack Obama announced the restoration of diplomatic relations. We quickly boarded a charter plane from New York to Miami and then to Havana. There was a real sense of excitement in the place. But he was not without protection. 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 wave from the balcony of a dilapidated apartment building across the street. For young Cubans in particular, this felt like a turning point: More opportunities, more access, more options seemed within reach.

Obama’s visit the following March further increased this feeling. Travel restrictions on Americans were loosened and limited trade began to resume. The embargo was still in effect as written in US law, but it was somewhat relaxed.

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

Even then there were restrictions. The Cubans had learned not to get ahead of themselves. For many, optimism came with the memory of how quickly it could fade. After all, not everyone believed that the United States should restart relations with this country. Many argued that normalizing ties would reward the communist government without forcing meaningful reforms.

Yet things were changing. Under the Fathom brand, Carnival Cruise Line docked in Havana in 2016, the first U.S. cruise ship to visit the island since 1978. As of November, JetBlue had direct flights from New York. For a while it felt like the barriers were breaking down in real time.

It was never easy to make news there. Permits can drop without warning. Phones rarely worked. Wi-Fi was difficult to find. Restaurants handed out long menus, but when you asked you were often told that rice and beans were all that was available. When I passed buildings with elegant facades, I would step inside to find them hollowed out, crumbled, little more than dust and debris.

Yet with each trip you could see little signs that the transformation was continuing. Family-run restaurants began to open in people’s homes. Airbnb listings are starting to spread. 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. Years ago, he had handed over power to his brother Raoul, but the death of the man who symbolized the revolution was a huge moment.

This time Havana was quiet.

The music stopped. Alcohol disappeared. The city entered a period of official mourning. People formed long queues to sign condolence books.

From the outside it looked like a clear ending. Not everything seemed so simple in Cuba.

Standing there, it was hard not to feel the energy of previous years disappearing. The same questions kept coming. What happens now? What about reforms? From relations with the United States?

When I left for the last time, I had the feeling that I had witnessed something rare, a brief period of time in which history accelerated, long-held patterns loosened just a little, and the future felt open for a moment.

In the years since, much of that momentum has slowed and, in some cases, reversed. The US withdrew its embassy staff, new travel restrictions were imposed in November 2017, and the flow of American visitors decreased. The openness that once felt within reach has given way to more familiar tensions; these tensions flare up like changes I never saw happening.

History doesn’t always come with a clear beginning or a clean ending. Cuba has a tendency to turn on itself.

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