The smart Cuba bet is on military strike but no regime change. It's the deportations, stupid
By Tim Padgett
May 28, 2026 at 6:00 AM EDT
COMMENTARY Prediction markets are betting President Trump will order military action in Cuba, but not regime change — as they know his priority is to make countries ripe for deportation, not democracy.
I agree with critics who call prediction markets crack cocaine for gambling addicts. But I also gotta agree with the Cuba odds the popular prediction platform Polymarket is posting.
That’s because they dovetail not with President Donald Trump’s desire for Cuban democracy, but with his lust for Cuban deportations.
Now that Trump has sent the U.S. aircraft carrier Nimitz into the Caribbean — you’ll remember he ordered the USS Gerald R. Ford there just weeks before U.S. special forces went into Venezuela on Jan. 3 — Polymarket says there’s a 51% chance the U.S. will have a “military clash” with Cuba in 2026.
But here’s the other Polymarket prediction that sounds right: it sees only a 21% chance that Cuba’s communist regime will fall in 2026.
So, Trump is likely to order a U.S. military strike on Cuba, but that operation is unlikely to re-democratize Cuba.
READ MORE: Maduro was a clown. Removing Castro would be a harder mission — as his indictment tells us
Which is precisely where we’ve been in Venezuela since Jan. 3, when U.S. commandos captured socialist dictator Nicolás Maduro, but essentially left his socialist dictatorship intact.
And it was left in place, led now by Maduro lieutenant and acting President Delcy Rodríguez, for economic purposes.
That is, to help Trump revitalize Venezuela’s oil industry so he can hold up the revenue gusher as proof that the country’s epic humanitarian crisis has been solved — and that it’s OK to deport hundreds of thousands of Venezuelan migrants in the U.S. back to the dystopia they fled.
In fact, one of the first, and false, declarations the Trump administration issued after expelling Maduro was that it was now perfectly fine for Venezuelan migrants to head home.
Trump's Caribbean missions are meant to make the case that deportees will now find prosperous red carpets there instead of disastrous red regimes.
Now pivot to Cuba — and wash, rinse, repeat.
Whatever Trump’s clash plan is for the island — Arresting the newly U.S.-indicted Cuban leader Raúl Castro? Blowing up the regime’s reported stockpile of attack drones? — its priority is most likely to force desperately needed economic reforms, not desperately needed political changes.
In other words: allowing Cuba’s regime (or a more cooperative, Rodríguez-style version of it) to stay in place as long as it helps Trump usher in capitalism, so he can hold up the investment windfall as proof that the country’s epic humanitarian crisis has been solved — and that it’s OK to deport hundreds of thousands of Cuban migrants in the U.S. back to the dystopia they fled.
Stateless purgatory
That could mean a half million deportees Trump’s reportedly demanding Cuba take back as a condition for loosening the de facto oil blockade and other economic chokeholds he’s clamped on the regime this year. Never mind that tightening those screws makes it even tougher for 500,000 deportees to survive if they’re returned.
Cuban migrants being put on a flight from the U.S. to Havana in February 2026. (1180x658, AR: 1.7933130699088147)
And it might include thousands of Cuban migrants the administration has booted to Mexico, where they’re dwelling in a quasi-stateless purgatory, according to a new report by the nonprofit Human Rights Watch.
Bottom line: That's what keeps Trump's MAGA voter base happy.
Still, even Trump knows it’s not the best optics to deport people, on the scale he’s engineering, back into the hellish situations that forced them out in the first place. That’s why he had his former Homeland Security Secretary Kristi Noem lie about conditions in gang-terrorized Haiti and insist it’s OK to deport 350,000 migrants there.
Problem is, one federal judge after another has concluded Noem’s reasoning was nuts.
But while Trump can’t make Haiti's gangs purchase Dow 30 shares instead of AR-15 rifles, he believes he can take gunboat control of Venezuela and Cuba — and build a convincing case that deportees will now find prosperous red carpets there instead of disastrous red regimes.
Meanwhile, actual regime change would just be a third wheel on Trump’s deportation date.
So Trump is still telling exiled Venezuelan opposition leader and Nobel Peace Prize winner María Corina Machado — the woman every poll in Venezuela says would win a new presidential election in a landslide, but who Trump shamelessly insists has no support in Venezuela — to stay put.
When Trump talks about Cuba, he crows that he’ll soon have “the honor of taking” the country into his Donroe Doctrine collection, or that making Secretary of State Marco Rubio, a Cuban-American, president of Cuba “sounds good to me.”
But the prediction markets don’t hear Trump mention restoring democracy.
It’s the deportations, stupid.
(1509x275, AR: 5.487272727272727)
I agree with critics who call prediction markets crack cocaine for gambling addicts. But I also gotta agree with the Cuba odds the popular prediction platform Polymarket is posting.
That’s because they dovetail not with President Donald Trump’s desire for Cuban democracy, but with his lust for Cuban deportations.
Now that Trump has sent the U.S. aircraft carrier Nimitz into the Caribbean — you’ll remember he ordered the USS Gerald R. Ford there just weeks before U.S. special forces went into Venezuela on Jan. 3 — Polymarket says there’s a 51% chance the U.S. will have a “military clash” with Cuba in 2026.
But here’s the other Polymarket prediction that sounds right: it sees only a 21% chance that Cuba’s communist regime will fall in 2026.
So, Trump is likely to order a U.S. military strike on Cuba, but that operation is unlikely to re-democratize Cuba.
READ MORE: Maduro was a clown. Removing Castro would be a harder mission — as his indictment tells us
Which is precisely where we’ve been in Venezuela since Jan. 3, when U.S. commandos captured socialist dictator Nicolás Maduro, but essentially left his socialist dictatorship intact.
And it was left in place, led now by Maduro lieutenant and acting President Delcy Rodríguez, for economic purposes.
That is, to help Trump revitalize Venezuela’s oil industry so he can hold up the revenue gusher as proof that the country’s epic humanitarian crisis has been solved — and that it’s OK to deport hundreds of thousands of Venezuelan migrants in the U.S. back to the dystopia they fled.
In fact, one of the first, and false, declarations the Trump administration issued after expelling Maduro was that it was now perfectly fine for Venezuelan migrants to head home.
Trump's Caribbean missions are meant to make the case that deportees will now find prosperous red carpets there instead of disastrous red regimes.
Now pivot to Cuba — and wash, rinse, repeat.
Whatever Trump’s clash plan is for the island — Arresting the newly U.S.-indicted Cuban leader Raúl Castro? Blowing up the regime’s reported stockpile of attack drones? — its priority is most likely to force desperately needed economic reforms, not desperately needed political changes.
In other words: allowing Cuba’s regime (or a more cooperative, Rodríguez-style version of it) to stay in place as long as it helps Trump usher in capitalism, so he can hold up the investment windfall as proof that the country’s epic humanitarian crisis has been solved — and that it’s OK to deport hundreds of thousands of Cuban migrants in the U.S. back to the dystopia they fled.
Stateless purgatory
That could mean a half million deportees Trump’s reportedly demanding Cuba take back as a condition for loosening the de facto oil blockade and other economic chokeholds he’s clamped on the regime this year. Never mind that tightening those screws makes it even tougher for 500,000 deportees to survive if they’re returned.
Cuban migrants being put on a flight from the U.S. to Havana in February 2026. (1180x658, AR: 1.7933130699088147)
And it might include thousands of Cuban migrants the administration has booted to Mexico, where they’re dwelling in a quasi-stateless purgatory, according to a new report by the nonprofit Human Rights Watch.
Bottom line: That's what keeps Trump's MAGA voter base happy.
Still, even Trump knows it’s not the best optics to deport people, on the scale he’s engineering, back into the hellish situations that forced them out in the first place. That’s why he had his former Homeland Security Secretary Kristi Noem lie about conditions in gang-terrorized Haiti and insist it’s OK to deport 350,000 migrants there.
Problem is, one federal judge after another has concluded Noem’s reasoning was nuts.
But while Trump can’t make Haiti's gangs purchase Dow 30 shares instead of AR-15 rifles, he believes he can take gunboat control of Venezuela and Cuba — and build a convincing case that deportees will now find prosperous red carpets there instead of disastrous red regimes.
Meanwhile, actual regime change would just be a third wheel on Trump’s deportation date.
So Trump is still telling exiled Venezuelan opposition leader and Nobel Peace Prize winner María Corina Machado — the woman every poll in Venezuela says would win a new presidential election in a landslide, but who Trump shamelessly insists has no support in Venezuela — to stay put.
When Trump talks about Cuba, he crows that he’ll soon have “the honor of taking” the country into his Donroe Doctrine collection, or that making Secretary of State Marco Rubio, a Cuban-American, president of Cuba “sounds good to me.”
But the prediction markets don’t hear Trump mention restoring democracy.
It’s the deportations, stupid.
(1509x275, AR: 5.487272727272727)