Monday, February 16, 2026

Cuba’s Problem: Too Close to the United States

 

By John Dorschner

For decades, analysts of Cuba have written that the island is Communist “despite being 90 miles from the United States.” I disagree: After years of studying Cuba, I believe a strong case can be made that it’s remained Communist for six decades “because it’s 90 miles from Miami.”

 My credentials: I co-authored a book, The Winds of December, a popular history covering the last weeks of 1958 and the first days of 1959 — the downfall of Batista and the coming to power of Castro. It received a favorable review on the cover of the New York Times Book Review by Hugh Thomas, considered by quite a few as the premier historian of Cuba.

Romania: Exiles Were Not an Impediment

In 2001, I received a Fulbright Senior Fellowship and went to Romania, where I taught journalism to university students and researched what happens to a post-Communist economy and how that might apply to Cuba.

Romania is an instructive tale: After the Berlin Wall fell, the state security hierarchy (truly nasty guys) said, “We are freedom-loving capitalists!” They executed the dictator and his wife and laid the groundwork for a quick conversion to a multi-party democracy with capitalistic principals. (To be sure, there were problems: Quite a few of those nasty guys became oligarchs and all those former Communist bureaucrats needed to make a living. For quite a while, starting a small business required getting something like 30 government permits, most of which involved bribes. Corruption continues to be an issue, but Romania is a stalwart member of NATO and the European Union.)

What about all those Romanian exiles whose properties been seized? Most of them had moved far away — Western Europe, Canada. The new government made small motions to compensate those who had lost land and factories, but it was minor and didn’t get amount to much — either as an impediment or an expense.

Not so with Cuba: The Communist Party in Cuba — from the very top to the middle and even low-level officials — know that angry Cubans are waiting a few miles away seeking vengeance: They want their land back, their factories, their houses, and they want many officials to be thrown in jail. Plenty of Miami Cubans, for example, have visited their former family homes and looked around — quietly planning for a time when they can take them back. The people who have lived in those structures for decades know they could lose their homes with regime change.

A revealing example can be seen in the comments that accompanied a recent post on the excellent website 14ymedio.com. The story involved three Cuban-American Congressmen asking Trump to formally charge Raúl Castro with shooting down the Brothers to the Rescue planes in 1996.

I did a lengthy investigation into the death of the four Miamians on those two Cessnas: It was indeed murder. A MiG pilot gunned down the defenseless planes, which were outside of Cuban airspace when they were destroyed. But what should be done about it?

In the comment section to the 14ymedio story, many were ecstatic about finally getting justice for the murders — targeting Raul and all the others in the military who were involved. Wrote one gleeful commentator: “Other charges against the dictatorship’s oligarch leadership include drug trafficking and terrorist sponsorship. Tyranny has no escape.”

“If There Is No Safe Exit…”

But a rare insight came from a commentator named Gabriel Delpino: “The downing of the planes was a serious event. The victims deserve memory and justice. That is not disputed. But the priority today is not revenge. It is the transition to democracy. When a leadership perceives that its only horizon is a Gaddafi-type end, the incentive changes. There is no longer political calculation. Only survival. And survival pushes hardening. In Eastern Europe, the transition was not built on revenge. With the exception of Romania, there were no lynchings or immediate settling of scores. There was negotiation, an agreed exit, guarantees. That made it easier to decompress the system. If the message now is ‘there will be no safe exit,’ the rational reaction of power is to entrench itself. Justice can and must come. But the order of priorities matters. First transition. Then responsibilities. Without a credible way out, there is no possible transition. And without transition, there will be no justice.”

In a recent Washington Post column, Lizette Alvarez, a veteran reporter and a Cuban-American, suggested that the best way forward is to negotiate changes with the present Cuban leadership, not try to kick it out. “Trump’s love of the deal and Cuba’s imminent collapse present a golden opportunity to finally drive meaningful change on the island,” she wrote.

I’m skeptical of Trump’s deal-making abilities, but I wholeheartedly embrace the concept of focusing on the need for change, not vengeance.

 

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