Two days ago, Senate Democrats tried to legally block Trump from using military force against Cuba.
The Senate stopped them – but just barely, 51 to 47.
DeSantis just explained to the Federalist Society exactly why Democrats are making that bet, and why Trump's Latin America wins could evaporate the moment he stops watching.
Delcy Rodriguez Is Already Running the Clock
Trump yanked Maduro out of Miraflores Palace in January and the foreign policy world treated it as a done deal.
DeSantis doesn't see it that way.
He called it "take off the head of the snake and then let the snake grow a new head."
He's describing Delcy Rodríguez – the woman who ran Maduro's oil ministry, brokered Venezuela's energy deals with Iran and Cuba, and is now running the country.
Trump has praised her for "doing a great job."
James Story, Trump's own former ambassador to Venezuela, said publicly that Rodríguez is doing "just enough to make it look as if they're complying" while waiting to see whether midterm elections weaken Trump's hand.
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Interior Minister Diosdado Cabello – the most powerful Chavista hardliner still standing – is still in the building.
The Venezuelan military's generals, several wanted by the U.S. on drug trafficking charges, are still in the building.
The colectivos – the armed street gangs that terrorized opposition voters for two decades – are still in the streets.
DeSantis nailed the mechanism: "They're just going to try to wait President Trump out."
Cuba Is the Harder Problem
On Cuba, DeSantis was blunter.
"Dicey," is how he described the prospect of the U.S. imposing change from outside.
"It just typically hasn't worked well for us," he said.
He's right, and sixty years of history back him up.
The Bay of Pigs failed in 1961 and handed Castro a propaganda victory that lasted decades.
Sanctions have been in place longer than most of the country's voters have been alive.
Castro died in his own bed in 2016.
His brother ran the country until 2018.
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The apparatus they built is still the only organized power on that island.
What makes the current moment different is that Trump is applying pressure the Castro regime has never faced – over 240 sanctions since January, an oil blockade squeezing Havana harder than anything since the Cold War, and enough military pressure that even Cuba's government believes it might be next.
Democrats know the pressure is working, which is why Tim Kaine, Adam Schiff, and Ruben Gallego just introduced a War Powers Resolution to strip Trump of the ability to act militarily against Cuba without congressional approval.
They lost, but barely.
The Only Win That Lasts Is Structural Change
DeSantis said he'd support Cuban exiles going back to help rebuild if real change created the opening.
"If real change created the opening" is the operative phrase – because right now it hasn't.
The Communist Party apparatus is intact.
The military hasn't fractured.
The population hasn't risen.
Venezuela is further along but still far from locked in.
Rodríguez is smart enough to give Trump the photographs he needs – signing oil reform bills, releasing political prisoners, restoring diplomatic relations – while Cabello's Chavista network sits underneath, intact, waiting.
Trump removed Maduro.
He hasn't replaced Maduro's machine.
DeSantis is the right person to say this out loud.
Florida's Cuban and Venezuelan exile communities have watched six administrations promise liberation and deliver disappointment.
They know what managed compliance looks like.
Republicans who want these gains to last past January 2029 should be asking which structural changes are actually locked in – and which ones are just waiting to be reversed.
Sources:
- A.G. Gancarski, "Dicey: Ron DeSantis details risk in U.S. ventures in Cuba, Venezuela," Florida Politics, May 21, 2026.
- Paul J. Saunders, "The US' Delcy Rodriguez Dilemma," The National Interest, February 2026.
- Orion Rummler, "Dem plot to limit Trump war powers on Cuba fails as GOP falls in line," Fox News, May 2026.
- Reuters, "Democrats push to rein in Trump on Cuba as White House steps up pressure," May 20, 2026.
- Manuel Rueda, "Venezuela's interim leader navigates U.S. demands, Chavista loyalty," NPR, February 5, 2026.
