Every time a Democratic president tries to “engage” with Cuba, the result is the same: the regime takes the money, makes empty promises, and keeps imprisoning dissidents. Biden’s Cuba policy was exactly that — and it’s time to say it bluntly.
Biden’s Mistake: Confusing Diplomacy with Concessions
The Biden administration inherited Trump’s maximum pressure policy and proceeded to dismantle it piece by piece. They reopened consulates, eased travel restrictions, increased permitted remittances, and removed Cuba from the state sponsors of terrorism list — briefly, before adding it back.
What did they get in return? Nothing. Absolutely nothing.
Cuba didn’t release political prisoners. It didn’t allow free elections. It didn’t open spaces for civil society. In fact, repression increased during the Biden era. After the 11J uprising in July 2021, the regime imprisoned over 1,000 protesters — many of them minors — and Biden responded with… statements of concern.
The Numbers of Failure
- Political prisoners: From 150 at the start of Biden’s term to over 1,000 after 11J. No significant release agreement reached
- Migration: More Cubans fled the island during Biden than in any comparable period in history. The 2022-2024 rafting exodus surpassed 1994
- Foreign investment in Cuba: Zero growth. International companies still won’t trust a system without property rights
- Human rights: Human Rights Watch and Amnesty International documented a consistent deterioration during the era of “engagement”
The Historical Lesson Democrats Keep Ignoring
Obama tried it. He restored diplomatic relations, visited Havana, embraced Raúl Castro at a baseball game. The world applauded. And Cuba didn’t change one bit. The regime used the opening to obtain hard currency from American tourism while continuing to repress its people.
It’s always the same movie: engagement without conditions empowers dictators. It gives them financial oxygen without demanding reforms. And worst of all — it tells the Cuban people that the free world has accepted their suffering as an acceptable price for “stability.”
What Trump Must Do Differently
The Trump 2.0 administration has started with the right strategy: maximum pressure. The oil blockade, reinforced sanctions, and “friendly takeover” rhetoric have put the regime in its weakest position in decades.
But pressure alone isn’t enough. Trump and Rubio must complement it with:
- Clear, public conditions: Internationally supervised free elections, release of all political prisoners, legalization of opposition parties
- A post-transition economic plan: Free trade zones, investment protections, property titles for Cubans who want to start businesses
- Direct support for dissidents: Funding for independent media, free VPNs, and diplomatic backing for organizations like the Assembly of the Cuban Resistance
- A regional coalition: Working with conservative governments in Argentina (Milei), Ecuador, and others to diplomatically isolate the regime
There Is No Middle Ground
With Cuba, “constructive engagement” doesn’t work. Dialogue without conditions doesn’t work. Soft pragmatism that confuses diplomacy with capitulation doesn’t work.
What works is sustained pressure with clear objectives and unconditional support for the Cuban people. Trump has a historic opportunity to do what no president has accomplished: being the one in office when Cuba was finally free.
The question is whether he’ll have the patience and consistency to stay the course. History is watching.
