As Trump turns to Cuba, he remembers how different things used to be

The White House has threatened to cut off Cuba’s oil supplies and take over the communist-ruled island on the back of military operations in Venezuela and Iran.

US President Donald Trump has hinted that the country is his next target, saying: “I think they can do whatever they want, whether it’s liberating them or taking them. They’re a very weakened country right now.” Cuba’s economy is in crisis due to oil shortages. But I was reminded of a time not too long ago when the two countries appeared to be normalizing relations after decades of hostility.

I first landed 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 officer that we were there as journalists, that we had permission, and that all formalities had been completed in advance. I appreciated that my team spoke Spanish and helped me through the process.

Parts of the city felt oddly familiar from the images I saw, with faded pastel buildings and old American cars with patchwork parts still somehow still running.

Cuba and the United States have been geopolitical adversaries for more than 50 years. When Fidel Castro came to power in the 1959 revolution, Cuba became communist and the island nation, just 90 miles from Florida, strengthened its ties with the Soviet Union. The Cuban government has seized U.S. real estate and U.S.-owned businesses in response to the expanding U.S. embargo. In response, President John F. Kennedy formally instituted a total embargo in 1962. Supplies of food, fuel, and consumer goods quickly became scarce.

But once I was there, I felt something starting to change.

Between 2012 and 2016, I traveled 10 times and served as a field producer for CNBC with international correspondent Michelle Caruso-Cabrera. Almost every visit seemed to coincide with a moment that felt like it might mark something important, a turning point. However, towards the end, the momentum suddenly became unstable.

When I first visited, Havana was trying to look like it was ready for the Pope. Fresh paint lined parts of the Malecon and was still drying in places along the route the pope was expected to travel. In a country shaped by communism for decades, his presence felt like more than just a religious event. It felt like a subtle but unmistakable signal that Cuba might be opening up.

After that, things started moving quickly.

Less than a year later, the government invited a small group of journalists, including us, to get an up-close look at what it called “reforms.” We spoke to central bank governors and small business owners who are trying to navigate a changing system, but not everything will change at once.

We skipped the official itinerary and headed to Hershey, Cuba, a town founded by Milton Hershey in the early 20th century to secure sugar for his chocolate business. It was one of several reminders of Cuba’s pre-revolutionary American past. The former Coca-Cola factory was being repurposed by the state. The Western Union building housed the country’s telecommunications company. The Woolworth store had become a local discount store.

In July 2015, President Barack Obama announced the restoration of diplomatic relations. We quickly left New York and traveled to Miami, where we boarded a chartered flight to Havana. You could really feel the excitement on set. But it wasn’t defenseless. People were hopeful but cautious.

A month later, the U.S. Embassy reopened for the first time in more than 50 years. I watched the flag go up from the balcony of a crumbling apartment building across the street. For young Cubans in particular, this felt like a turning point. More opportunities, more access, more choices seemed within reach.

President Obama’s visit in March of the following year further reinforced that feeling. Travel restrictions for Americans have been eased and limited trade has begun to resume. The embargo remains in place, as provided by U.S. law, but has been slightly relaxed.

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

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

Still, things were changing. In 2016, the Fathom-branded Carnival Cruise Line docked in Havana, becoming the first U.S. cruise ship to visit Havana since 1978. By November, JetBlue offered nonstop flights from New York. For a while, it felt like barriers were being broken down in real time.

Reporting there was never easy. Permits may expire without warning. Phone calls were almost unreliable. It was difficult to find Wi-Fi. Restaurants handed out long menus, but when we asked, we were often told they only had rice and beans. Sometimes I would walk past a building with an elegant façade and step inside to find it hollow and crumbling, little more than dust and rubble.

Yet, with each trip, there were small signs that change was continuing. Family-run restaurants began opening in people’s homes. Airbnb listings are starting to spread. It wasn’t dramatic, but it was there.

My last visit was in November 2016, shortly after Fidel Castro’s death, to cover his funeral. He had handed over power to his brother Raul years earlier, but the revolutionary icon’s death was a big moment.

Havana was quiet this time.

The music stopped. Alcohol is gone. The city has entered an official period of mourning. People stood in long lines to sign condolence forms.

From the outside, it looked like a clear end. Inside Cuba, I felt it was not so simple.

As I stood there, I couldn’t help but feel that all the energy I had had was gone. The same question came back over and over again. What is happening now? What will happen to the reforms? What about the relationship with America?

When I left here for the last time, I felt like I had witnessed something unusual, where history seemed to accelerate, long-standing patterns loosened, even if only slightly, and the future seemed to open up for just a moment.

In the years since, much of that momentum has slowed and, in some cases, reversed. The United States withdrew its embassy staff and imposed new travel restrictions in November 2017, and the flow of American visitors dwindled. The opening that once felt within reach is replaced by a more familiar tension, flaring up as if the changes I saw had never happened.

History does not always come with a clear beginning or a clear end. In Cuba, it tends to come back to itself.

What happens next between these two neighbors is yet to be written.