Ever since the overthrow of the Fulgencio Bautista regime in 1959, Cuba has been shunned by the United States. Now, following the capture of former Venezuelan PresidentEver since the overthrow of the Fulgencio Bautista regime in 1959, Cuba has been shunned by the United States. Now, following the capture of former Venezuelan President

Trump poised to make a failed state even worse: George Will

2026/06/25 00:30
3 min read
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Ever since the overthrow of the Fulgencio Bautista regime in 1959, Cuba has been shunned by the United States. Now, following the capture of former Venezuelan President Nicolás Maduro and months of U.S. military strikes against Iran, President Donald Trump is indicating that a U.S military invasion of Cuba is possible. But conservative Washington Post columnist George Will fears that Trump could make a bad situation in Cuba even worse.

"After beginning the war, but before his conduct of it turned it into an embarrassment, President Donald Trump said: 'On the way back' from Iran, 'we will be taking over' Cuba 'almost immediately,'" Will explains. "Now, humiliated and bewildered, he hungers for a success before this autumn's elections."

The 84-year-old Will, who was a scathing critic of the late Fidel Castro, is no fan of the communist regime in Cuba — which has been suffering from a terrible economy, a crumbling infrastructure, and frequent blackouts. But he fears that if Trump does move forward with a U.S. military invasion of Cuba, things will only become more dire for the troubled island nation.

"Communist Cuba, a threadbare museum of Marxism, has always attracted tyranny tourists, leftist pilgrims eager to experience, briefly, applied socialism," Will argues in the Post. "The only good its evil ever produced is 'Against All Hope,' Armando Valladares' magnificent 1986 memoir of 22 years as a political prisoner. Beatings were never perfunctory, always ferocious and imaginatively cruel.… Other than those pilgrims, no one believes the Havana regime has a shred of legitimacy. What should be done?"

The Never Trump conservative continues, "For decades, Communist Cuba, a mendicant nation prickly about its revolutionary dignity, depended on subsidies from the Soviet Union, then on bartered oil from Venezuela. Now, it experiences electricity blackouts sometimes lasting 22 hours a day. Some airlines have stopped serving Havana because fuel is scarce for return trips. Tourism has evaporated."

But Will emphasizes that while Cuba's situation is dire, Trump doesn't appear to have a coherent game plan.

"In January," Will observes, "Trump said, 'Cuba is ready to fall.' Into what? Has Trump thought through his vow to 'take care' of Cuba with a 'friendly takeover' during 'a little brief stopover'? Before he skittered away from demanding Iran's 'unconditional surrender,' he jovially said of Cuba: A U.S. aircraft carrier will 'stop about 100 yards offshore, and they'll say: Thank you very much. We give up.' Such a cutup. Our Metternich from Midtown Manhattan is not intimidated by the aphorism that if you want to make God laugh, tell him your plans."

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