Trump's moves in Venezuela, Cuba risk being Hormuz miscalculations - not hemispheric makeovers
By Tim Padgett
April 30, 2026 at 6:00 AM EDT
COMMENTARY In Venezuela and Cuba, President Trump risks repeating the miscalculation he's made in Iran and the Strait of Hormuz — thinking bold strikes automatically yield regime change.
President Donald Trump’s Iran war — and Iran’s retaliatory closure of the Strait of Hormuz to much of the world’s oil shipping — is his millstone of the moment.
Despite the U.S. military's commanding performance, the Hormuz debacle is a grand miscalculation that could define Trump's legacy if he doesn’t resolve it asap.
But even if Trump finds an exit ramp in the Middle East, he’s got two potential Hormuz homologues developing in his own hemisphere, in Venezuela and Cuba.
There, as in Iran, his warrior promises of regime change are looking less likely to be kept, because his planning didn’t match his pugnacity.
READ MORE: If regime change doesn't come in Venezuela, Trump will have handcuffed himself alongside Maduro
If you need proof of that fear inside Venezuela, I'd look at a newly released poll there from the Caracas firm Meganálisis.
Almost 90% said they disapprove of Trump’s vocal support of interim President Delcy Rodríguez — who was the top lieutenant of dictator Nicolás Maduro before U.S. special forces nabbed him in Caracas on Jan. 3 and flew him to New York to face drug-trafficking charges.
Here’s a big reason for that disapproval: 94% say Rodríguez is moving too slowly, if at all, to steer post-Maduro Venezuela back to democracy — in spite of Trump’s claim that he’s now “running” the country with Rodríguez as his caretaker.
Venezuelans are afraid that Rodríguez and Maduro’s left-over regime are simply buying time while betting that Trump — as his rhetoric has certainly indicated — cares more about U.S. control of Venezuela’s oil reserves, the world’s largest, than about the country’s re-democratization.
Rodríguez and company indeed seem willing to indulge the former — but look even more intent on keeping the latter from ever happening.
Trump may think flaunting his newly acquired oil matters more than showing off a newly elected democracy — but the rest of the world doesn’t think so.
Some examples:
Last week, Rodríguez announced that an amnesty period her regime recently OK’d in Venezuela will now be ending — even though about half the country’s political prisoners, almost 500, remain behind bars.
Meanwhile, 87% in the Meganálisis survey said Venezuela should hold a new presidential election this year, and three-fourths said they’d vote for democratic opposition leader and Nobel Prize winner María Corina Machado, who remains in exile. But the Rodríguez cabal has put the kibosh on a timely vote — and continues to threaten Machado with imprisonment if she returns.
Cuban President Miguel Diaz-Canel, center, attends a celebration marking the 65th anniversary of the proclamation declaring the Cuban Revolution socialist, in Havana, Cuba, on April 16, 2026. (6261x4174, AR: 1.5)
Left-wing mafia
Which raises a big problem for Trump: the transactional dealmaker may think that flaunting his newly acquired South American crude matters more than showing off a newly elected democratic government — but the rest of the world doesn’t.
To most people, if Venezuela continues indefinitely with Rodríguez and her authoritarian left-wing mafia intact, Trump's stunning Maduro capture — which he hopes will rank up there with Barack Obama’s Osama bin Laden operation — will ultimately go down in history as a failure.
Which raises a bigger problem: to dislodge that entrenched mafia, he might have to stage another, more serious military mission — which would be politically toxic in the run-up to November’s mid-term elections.
It’d be as poisonous as putting U.S. boots on the ground in Iran — or, as Trump has threatened, annihilating the country’s “civilization” — to bring down its theocratic thugs, take out its nuclear bomb-making capacity and re-open the Strait of Hormuz.
And it’d be as ugly as a U.S. military strike in the third potential Hormuz on Trump’s bingo board: Cuba.
Trump may have to resort to that if, as it appears, his blockade of oil shipments to Cuba doesn’t topple its communist dictatorship as expeditiously as he led Cubans and the rest of us to believe it would.
Trump was certain, given the island’s bottomless economic suffering, that his energy strangulation would have Raúl Castro and the Central Committee begging to negotiate a conversion to democracy and capitalism — to give Trump, as he put it, “the honor of taking Cuba.”
But apparently nobody told Trump that Marxist Cuban zealots are as bullheaded as Muslim Iranian fanatics — and that even a middling apparatchik like Cuban President Miguel Diaz-Canel, when all but ordered by the Trump administration to step down before his Tropical Titanic sinks into the Caribbean, would insist that Cuba’s failed and oppressive system “is not up for negotiation.”
Perhaps Trump’s impulsive moves in Venezuela and Cuba will eventually overhaul those countries. I hope so.
For now, though, he’s risking legacies there that look more like Hormuz miscalculations, not hemispheric makeovers.
(1509x275, AR: 5.487272727272727)
President Donald Trump’s Iran war — and Iran’s retaliatory closure of the Strait of Hormuz to much of the world’s oil shipping — is his millstone of the moment.
Despite the U.S. military's commanding performance, the Hormuz debacle is a grand miscalculation that could define Trump's legacy if he doesn’t resolve it asap.
But even if Trump finds an exit ramp in the Middle East, he’s got two potential Hormuz homologues developing in his own hemisphere, in Venezuela and Cuba.
There, as in Iran, his warrior promises of regime change are looking less likely to be kept, because his planning didn’t match his pugnacity.
READ MORE: If regime change doesn't come in Venezuela, Trump will have handcuffed himself alongside Maduro
If you need proof of that fear inside Venezuela, I'd look at a newly released poll there from the Caracas firm Meganálisis.
Almost 90% said they disapprove of Trump’s vocal support of interim President Delcy Rodríguez — who was the top lieutenant of dictator Nicolás Maduro before U.S. special forces nabbed him in Caracas on Jan. 3 and flew him to New York to face drug-trafficking charges.
Here’s a big reason for that disapproval: 94% say Rodríguez is moving too slowly, if at all, to steer post-Maduro Venezuela back to democracy — in spite of Trump’s claim that he’s now “running” the country with Rodríguez as his caretaker.
Venezuelans are afraid that Rodríguez and Maduro’s left-over regime are simply buying time while betting that Trump — as his rhetoric has certainly indicated — cares more about U.S. control of Venezuela’s oil reserves, the world’s largest, than about the country’s re-democratization.
Rodríguez and company indeed seem willing to indulge the former — but look even more intent on keeping the latter from ever happening.
Trump may think flaunting his newly acquired oil matters more than showing off a newly elected democracy — but the rest of the world doesn’t think so.
Some examples:
Last week, Rodríguez announced that an amnesty period her regime recently OK’d in Venezuela will now be ending — even though about half the country’s political prisoners, almost 500, remain behind bars.
Meanwhile, 87% in the Meganálisis survey said Venezuela should hold a new presidential election this year, and three-fourths said they’d vote for democratic opposition leader and Nobel Prize winner María Corina Machado, who remains in exile. But the Rodríguez cabal has put the kibosh on a timely vote — and continues to threaten Machado with imprisonment if she returns.
Cuban President Miguel Diaz-Canel, center, attends a celebration marking the 65th anniversary of the proclamation declaring the Cuban Revolution socialist, in Havana, Cuba, on April 16, 2026. (6261x4174, AR: 1.5)
Left-wing mafia
Which raises a big problem for Trump: the transactional dealmaker may think that flaunting his newly acquired South American crude matters more than showing off a newly elected democratic government — but the rest of the world doesn’t.
To most people, if Venezuela continues indefinitely with Rodríguez and her authoritarian left-wing mafia intact, Trump's stunning Maduro capture — which he hopes will rank up there with Barack Obama’s Osama bin Laden operation — will ultimately go down in history as a failure.
Which raises a bigger problem: to dislodge that entrenched mafia, he might have to stage another, more serious military mission — which would be politically toxic in the run-up to November’s mid-term elections.
It’d be as poisonous as putting U.S. boots on the ground in Iran — or, as Trump has threatened, annihilating the country’s “civilization” — to bring down its theocratic thugs, take out its nuclear bomb-making capacity and re-open the Strait of Hormuz.
And it’d be as ugly as a U.S. military strike in the third potential Hormuz on Trump’s bingo board: Cuba.
Trump may have to resort to that if, as it appears, his blockade of oil shipments to Cuba doesn’t topple its communist dictatorship as expeditiously as he led Cubans and the rest of us to believe it would.
Trump was certain, given the island’s bottomless economic suffering, that his energy strangulation would have Raúl Castro and the Central Committee begging to negotiate a conversion to democracy and capitalism — to give Trump, as he put it, “the honor of taking Cuba.”
But apparently nobody told Trump that Marxist Cuban zealots are as bullheaded as Muslim Iranian fanatics — and that even a middling apparatchik like Cuban President Miguel Diaz-Canel, when all but ordered by the Trump administration to step down before his Tropical Titanic sinks into the Caribbean, would insist that Cuba’s failed and oppressive system “is not up for negotiation.”
Perhaps Trump’s impulsive moves in Venezuela and Cuba will eventually overhaul those countries. I hope so.
For now, though, he’s risking legacies there that look more like Hormuz miscalculations, not hemispheric makeovers.
(1509x275, AR: 5.487272727272727)