Cuba Should Accept Trump's 'Friendly Takeover'

Daniel McCarthy
Mon, 09 Mar 2026 14:57:51 -0700
Opinion

President Donald Trump has shown Cuba's communist rulers two ways their reign over the island can end: the Maduro way or the Khamenei way.

The Cuban regime is a mix of gerontocracy, nepotism and socialism. Its official face is President Miguel Diaz-Canel, but supreme authority still emanates from the 94-year-old Raul Castro, brother of the state's founding dictator, Fidel Castro.

Though the long-lived Castro clan seems to prove only the good die young, no one beats the actuarial tables in the end, and Raul's days are drawing short.
Updated: Mon Mar 09, 2026

President Donald Trump has shown Cuba's communist rulers two ways their reign over the island can end: the Maduro way or the Khamenei way.

The Cuban regime is a mix of gerontocracy, nepotism and socialism. Its official face is President Miguel Diaz-Canel, but supreme authority still emanates from the 94-year-old Raul Castro, brother of the state's founding dictator, Fidel Castro.

Though the long-lived Castro clan seems to prove only the good die young, no one beats the actuarial tables in the end, and Raul's days are drawing short.

Cuba is overdue for a profound change, and Trump is determined to bring it about.

It's been a lifelong goal of the Cuban American who now serves as U.S. secretary of state, too.

What Trump and Marco Rubio have planned won't look exactly like the operation that captured Venezuelan strongman Nicolas Maduro or the obliteration of Ayatollah Khamenei and most of his senior staff in the war now being waged against Iran.

But Cuban officials have seen just how far the Trump administration is willing to go. They've been educated by example, and now they have a choice to make: do they work out a deal with America, or do they take their chances with an administration that's become very comfortable with the use of force?

For now, Trump is using economic leverage to bring Havana around.

"The Cuban government is talking with us, and they're in a big deal of trouble. They have no money. They have no anything right now," Trump said Feb. 27, before musing, "maybe we'll have a friendly takeover of Cuba."

Venezuela suggests what that would look like: Maduro is gone, but the rest of the regime is still in place with Maduro's deputy, Delcy Rodriguez, in charge.

Yet Rodriguez is cooperating with the United States — more than Maduro ever did, at any rate — diplomatic relations have been reestablished, and economic connections are burgeoning.

Venezuela isn't free, but it's freer than before, and Trump is keeping the socialist regime on a short leash: if its leaders don't want to wind up like Maduro, or Khamenei for that matter, they can't behave toward their own people or America the way Maduro did.

Maduro's fall was a crushing blow to Cuba, which depended on cheap fuel supplied by Venezuela in the spirit of Marxist comradeship and mutual anti-Americanism.

Now Havana's red regime is alone — and poorer than ever.

That gives Trump and Rubio an opening to bring change to Cuba through economic rather than military persuasion, with the threat of force, however, unmistakably lingering in the background.

As early as January, according to the Wall Street Journal, the Trump administration was on the hunt for Cuban government insiders who might be willing to work with America to remake the regime from within, much as Maduro's ouster was facilitated by elements close to his own inner circle.

Some of the administration's overtures are hardly covert. Last month, Axios reported Rubio has been having, in the words of an unnamed American official, "'discussions' about the future" with Raul Castro's influential grandson, also named Raul (or "Raulito").

In late February, Trump eased export controls and began allowing American companies to start exporting diesel and other petroleum products to Cuba.

And there's a bigger economic package in the works, one dramatic enough to lead to what a clever headline in USA Today calls "Cubastroika."

Those are carrots, but Trump is also getting a stick ready, in the form of potential prosecutions of Cuban leaders in American courts for a host of crimes, including drug offenses and human trafficking.

Maduro languishes in Brooklyn's Metropolitan Detention Center today because of similar indictments. What happened to him will happen to Cuban leaders, too, if they're not smart.

Trump is poised to succeed where earlier presidents failed because he's trying to do neither too much nor too little.

Former President Barack Obama made no effort to change the Castro regime's character and orientation, so his economic openings to Cuba only enriched a tyrannical and hostile government.

Earlier Republican presidents refused to do that, but the economic restrictions they kept in place only froze the regime in place — it couldn't grow, but it wouldn't die.

Trump, by contrast, doesn't accept the status quo: 35 years after the fall of the Soviet Union, how can there still be a Communist state 90 miles off our coast?

The president isn't expecting Thomas Jefferson to replace Raul Castro or Miguel Diaz-Canel. The transition to democracy can take time, and the old regime can exit with a parachute, if it makes a deal.

But the Western hemisphere is our neighborhood, and it doesn't have room for the economic or ideological equivalent of a crack house — not in this century.

Cuba has a bright future, but those in charge in Havana today will have no future at all if they rebuff the friendly takeover Trump offers.