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

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

U.S. President Donald Trump is implying the country is his next target, saying: “Whether I free it, take it,  I think I can do anything I want with it. They’re a very weakened nation right now.” The oil shortage is bringing Cuba’s economy to the brink. But I’ve found myself thinking back when, not that long ago, it briefly looked like the two nations would normalize relations after decades of hostility.

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

Parts of the city felt strangely familiar from images I’d seen of faded pastel buildings and old American cars somehow still running on patched-together parts.

Cuba and the U.S. had been geopolitical foes 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 U.S. property and American-owned businesses in response to a growing U.S embargo. In response, President John F. Kennedy formalized a full embargo in 1962. Supplies of food, fuel, and consumer goods quickly became scarce.

But being there, I sensed that something was beginning to shift.

Between 2012 and 2016, I made 10 trips, field producing for CNBC with international correspondent Michelle Caruso-Cabrera. Almost every visit seemed to line up with something significant — moments that felt like they might mark a turning point. But by the end, that momentum felt suddenly uncertain.

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

After that, things started to move quickly.

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 central bank governor, and with small business owners trying to navigate a system that was changing, but not all at once.

We slipped away from the official itinerary and made our way to Hershey, Cuba, a…