The streets of Havana are usually defined by a forced, quiet resilience, but the recent wave of protests has shattered that facade. This isn't just another minor scuffle over food rations. It's a fundamental break in the social contract that has kept the island under a singular thumb for decades. Donald Trump has signaled he's watching. He's not just watching; he’s suggesting he might be the one to finally "make a deal" with a post-uprising Cuba.
If you’ve followed the history of U.S.-Cuba relations, you know it's a graveyard of failed policies and broken promises. We’ve seen the Cold War brinkmanship, the Obama-era "thaw," and the Trump-era "maximum pressure" campaign. Now, with the Cuban government appearing more fragile than ever, the prospect of a massive geopolitical shift is back on the table. Trump's rhetoric isn't just bluster this time. It reflects a specific strategy that treats international diplomacy like a real estate acquisition where the seller has run out of options.
The leverage of a failing state
The current protests in Cuba aren't happening in a vacuum. The island is facing its worst economic crisis since the collapse of the Soviet Union. We're talking about daily blackouts that last eighteen hours. We're talking about a lack of basic medicine and bread. When people take to the streets in a country where doing so can land you in a cell for twenty years, they aren't doing it for fun. They're doing it because they have nothing left to lose.
Trump sees this desperation as the ultimate leverage. His previous administration moved to reverse almost every opening created by the Obama administration. He added Cuba back to the State Sponsors of Terrorism list. He restricted remittances. He essentially tried to starve the regime of hard currency. Now, he’s betting that the pressure has reached a boiling point. The idea is simple: the regime is so desperate for a lifeline that they might actually agree to the kind of concessions they’ve rejected for sixty years.
Why this deal would look different
In the past, "deals" with Cuba were about incrementalism. A little more travel here, a little more cigar trade there. Trump doesn't do incrementalism. If he’s talking about a deal following an uprising, he’s likely looking for something structural. He’s looking for the kind of opening that allows American investment to flood the island while demanding a pullback of Chinese and Russian influence.
Cuba has become a strategic playground for America's rivals. Russia has been eyeing the restoration of intelligence bases. China has its foot in the door with telecommunications and infrastructure. For a U.S. president focused on "America First," a deal with Cuba isn't just about helping the Cuban people. It’s about clearing the Western Hemisphere of adversarial military footprints.
Honestly, the Cuban leadership is in a corner. They can’t feed their people, and they can’t stop the internet from showing those people what they’re missing. The old guard is dying off. The new leaders, like Miguel Díaz-Canel, don't have the revolutionary "charity" that Fidel Castro used to keep the population in line. They only have force. And force is expensive.
The Florida factor and the 2024 math
You can't talk about Trump and Cuba without talking about Miami. The political reality is that any move regarding the island is filtered through the lens of the Cuban-American vote. In 2020, Trump saw a massive swing in his favor in Miami-Dade County. That wasn't an accident. It was the result of a consistent message that the Democratic party was "soft" on socialism.
By suggesting a deal now, Trump is threading a very needle-thin gap. He has to promise the hardliners that he won't give the regime a free pass, while simultaneously offering a vision of a "liberated" Cuba that attracts younger voters who want to see their families thrive. It’s a gamble. If he leans too far into the "deal" side, he risks looking like he's bailing out the communists. If he stays too hardline, he misses the chance to be the "liberator" who oversaw the fall of the Caribbean's last Marxist outpost.
What a real uprising actually changes
Uprisings are messy. They don't usually end with a neat signature on a piece of paper. The 2021 protests were a shock to the system, but the 2024 and 2025 flares have been different. They are more decentralized. They are happening in the provinces, not just Havana. This makes them harder for the Black Berets—the regime’s elite suppression force—to squash all at once.
If the Cuban government actually sits down at a table with Trump, they’ll be doing it from a position of near-total collapse. That’s exactly where Trump likes his counterparts. Think back to the North Korea summits. Whether you think those were successful or not, they proved one thing: Trump is willing to sit with anyone if he thinks the optics and the "win" are big enough. Cuba is much closer to home. The stakes are much higher.
The risks of a bad bargain
There is a huge danger here. If the U.S. offers a deal that provides economic relief without ironclad guarantees for human rights and free elections, it just finances the next generation of the dictatorship. We saw a version of this with the 2015 thaw. Money flowed in, but it mostly went to GAESA, the military-run conglomerate that controls almost every profitable sector of the Cuban economy. The average Cuban saw very little of that "opening."
Any "Trump Deal" would have to bypass GAESA entirely. That’s almost impossible under the current Cuban legal framework. It would require the Cuban government to effectively dismantle its own economic power base. Would they do it? Probably not willingly. But when the lights go out and the pantry is empty, "willingly" becomes a relative term.
Moving beyond the Cold War rhetoric
We’re entering a phase where the old "Embargo vs. Engagement" debate feels like a relic. The internet changed the game. Cubans are using VPNs to see the world. They’re using crypto to receive money because the government takes a huge cut of traditional wire transfers. They’re already finding ways to bypass the regime.
If Trump wants to make a deal that actually sticks, he should focus on the digital and financial sovereignty of the Cuban people. Support the entrepreneurs. Support the people who are fixing old cars and running private hostals. Those are the people who will actually rebuild the country, not the generals in olive drab.
The next few months are going to be volatile. Watch the rhetoric coming out of Mar-a-Lago and compare it to the activity in the Port of Mariel. If you see signs of "backchannel" communications, it means the deal-making has already started. The uprising provided the opening. Now we see if anyone has the guts to walk through it.
Keep an eye on the specific demands regarding the State Sponsors of Terrorism list. That’s the biggest chip the U.S. holds. If that list starts being used as a bargaining tool, the deal is officially in motion. Don't expect a quiet transition. Expect fireworks, both literal and political.
