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For decades, starting with the passage of the Cuban Adjustment Act in 1966, refugees and asylum seekers from Cuba enjoyed a distinctly smooth pathway to legal residency in the US. In a typical cold-war-era “combination of hard and soft power,” Ada Ferrer and Miriam Pensack write in our July 23, 2026, issue, “the US imposed sanctions intended to bring Castro’s government to the point of collapse and at the same time made a point of showing benevolence toward refugees fleeing the regime, touting their exodus as proof of communism’s failure.” Many ended up in Miami, where they became profoundly identified with the city itself.

Since the start of his second term, Ferrer and Pensack write, Donald Trump “has summarily dismantled that approach,” deporting thousands of Cubans and issuing deportation orders to tens of thousands more. Even as his administration forces out Cuban migrants, it has “dedicated itself to exacerbating the crisis to which they will return,” subjecting the island to a fuel embargo that has pushed its economy and society toward ruin. In Miami, these changes have reshaped daily life. “Tens of thousands of Cubans in the city remain in anxious suspension,” Ferrer and Pensack report, “unsure what might happen in Cuba and what fate awaits their family members on both sides of the Florida Straits.”

Below, alongside Ferrer and Pensack’s essay, we have collected five dispatches from our archive on Cuba.

Ada Ferrer and Miriam Pensack
Broken Promises in Cuban Miami

Donald Trump has reversed the government’s longstanding benevolence toward Cuban asylum seekers, even as his administration exacerbates the crisis they fled.

Joshua Jelly-Schapiro
Life on the Verge

“‘On the verge.’ It’s a phrase that has been applied to Cuba at many moments during its recent history.”

—April 5, 2018

Alma Guillermoprieto
Cuba: The Big Change

“The joke on everyone’s lips was that Obama should stay in Havana for a month, because in preparation for his three-day visit more had been done to fix up the place than in the previous half-century. In fact, the visit is happening because enormous change has already taken place, most of it at the urging of Raúl Castro, but there is only occasional grudging recognition of that. ‘Things are better,’ an outspoken woman I know said, ‘but not enough.’”

—May 12, 2016

Esther Allen
Cuba: We Never Left

The hoisting of the Star-Spangled Banner in Havana on Friday, for the first time in more than half a century, has been met with perplexing and contradictory reactions in the United States.

—April 14, 2015

Jeri Laber
Is Cuba Really Changing?

“Cuba has been described as ‘the Soviet Union with palm trees,’ and one can readily see why, both in the forms that its repression has taken and in the economic failure that has forced it to seek a new image internationally.”

—April 20, 1995

Arthur Schlesinger Jr.
Four Days with Fidel: A Havana Diary

“At this point Castro, who has been listening carefully and occasionally taking notes, calmly interjects: ‘The Soviets had far more military experience, so we had unlimited confidence in them. When we had an opinion, we offered it, but we thought they knew better than we did. I remember Nikita saying, ‘We have missiles that can hit a fly.’”

—April 20, 1995

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