With so much attention on Iran in recent weeks, you may have missed the news about the increasingly tense situation with another longtime adversary of the United States – one closer to home.

On April 13, while making remarks about the war in Iran, President Trump said, “We may stop by Cuba after we’re finished with this.”

The U.S. has blocked nearly all oil shipments into Cuba, pushing it to the brink of collapse. Meanwhile, high-level talks between the two countries are underway.

Mr. Trump hasn’t offered details, but has said this: “All my life I’ve been hearing about the United States and Cuba: when will the United States do it? I do believe I’ll be the honor, having the honor of taking Cuba.”

The island nation just 90 miles from Florida has indeed played an outsized role in our foreign policy for close to 70 years. But back in the 1950s, most Americans thought of Cuba as little more than a hedonistic paradise.

It was “a playground where anything goes, where there are casinos, where there’s prostitution … and to a great extent, that was true,” said Jorge Malagon Marquez, a Cuban-American, and a professor of history at Miami Dade college. “You had celebrities like Frank Sinatra coming down. It’s party time.

“What Americans weren’t seeing was the dissatisfaction amongst regular Cubans running just below the surface,” he said.

Many Cubans were subsisting, and working in industries outright owned by Americans. “Cubans loved Americans coming as tourists or what have you, but it was the control of the economy that really bothered them,” Marquez said. And for many Cubans, memories were still fresh from half a century earlier when, after the Spanish American War, the U.S. won a “sort of” independence for Cuba in 1902.

But was Cuba really independent? “It’s independence like independence I gave my teenage kids,” laughed Marquez, “which means like, ‘Sure, you’re independent, so long as you’re home by 10 o’clock.'”

Yes, Cuba was a sovereign nation, but the United States could intervene anytime its interests were at stake – which it did repeatedly, until the 1930s. And so, by the late 1950s, conditions were ripe for revolution.

But if other Latin American countries had grievances against the United States, what was it about Cuba that allowed a decades-long communist dictatorship to take root there? “It’s Fidelismo,” said Marquez. “It’s a cult of personality. If it had been anybody else, this would’ve fizzled out within the first couple of years.”

The late Fidel Castro came to power in 1959, and became a central actor in the Cold War, sparking fears of Communism spreading in the Americas. His authoritarian regime has survived a decades-long trade embargo … a missile crisis that brought the world to the brink of nuclear war … and the collapse of the Soviet Union, Cuba’s longtime patron.

Marquez still remembers the hold Castro had over a five-year-old growing up in Cuba: “I was, like, in first grade or just starting first grade. And they have something called the Pioneers for the Revolution – you wear a red scarf. And they would ask, ‘Bow your heads and pray to God for candy.’ And the children would bow their heads and pray to God for candy … and open your eyes.”

After no candy appeared, the children would be told, “‘Bow your heads, close your eyes, and ask Fidel for candy.’ … I wish I were making this up! And lo and behold, there will be the candy.”

Marquez and his family fled Cuba in 1967, among the more than 1.5 million who have left the island for the U.S. since the early 1960s.

Elsa and Becky Cobo’s late father, Arturo, was a teenager in Havana in 1960 when he witnessed his own father’s bank being seized by the regime. “He saw the military come and take basically the keys from my grandfather and tell him, ‘Go,’ and that’s when he said, ‘We gotta do something,'” said Elsa.

Arturo escaped to the U.S., and enlisted in the CIA-trained brigade of Cuban exiles who, in April 1961, landed at Cuba’s Bay of Pigs in a secret operation meant to overthrow the Castro regime. The soldiers were expecting air cover from the Americans. At the last minute, though, Democratic President John F. Kennedy pulled the plug – a turn of events Cuban-Americans never forgot.

“They were basically left there to die,” said Elsa.

Asked why so many Cuban-Americans are so staunchly Republican, Marquez replied, “Bay of Pigs. That’s it. You don’t have to go further than that.”

Arturo Cobo spent nearly two years in a Cuban prison. When he was released, he settled in Key West, Fla., where his daughters still live today.

There, Arturo helped wave after wave of refugees arriving from his home country. Many didn’t survive the voyage.

At the Key West Botanical Garden, you can see evidence of their desperation – makeshift rafts used by Cubans to reach America, some made of Styrofoam.

Arturo Cobo died in 2019. He, like so many others who fled Castro’s Cuba, never returned. “They came over hoping that one day Cuba would be free,” said Becky, “and never imagined … they would not see the day that that would happen.”

Jorge Malagon Marquez says those waves of migration have remade South Florida. But their absence in Cuba may also help explain the regime’s longevity: “Those that would have been willing to rise up? Gone. I mean, you gotta give it to Fidel Castro. He was brilliant, you know, in a sort of, like, evil way. He was the evil genius.”

But Castro died in 2016, and the Cold War is long over. Few believe Cuba poses the threat that it once did to the U.S. The Cuban economy, never robust under communist rule, has been in freefall since the pandemic, with nearly a fifth of the population leaving since 2021.

And now the Trump administration is turning the screws on an already-failing state, worsening its humanitarian crisis. Mr. Trump said of Cuba, “Whether I free it, take it, I think I can do anything I want with it.”

Cubans on both sides of the Florida Straits are pondering what comes next.

     
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Story produced by Mark Hudspeth. Editor: Emanuele Secci. 

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