Donald Trump has repeatedly taken a hard-line stance on Cuba, portraying the island’s communist government as repressive and promising to tighten U.S. policy until there is political change in Havana.

Key things Trump has said about Cuba

  • In June 2017, Trump declared in Miami: “Effective immediately, I am canceling the last administration’s completely one-sided deal with Cuba,” referring to rolling back Barack Obama’s opening to the island.
  • In that same speech, he said his goal was “a much better deal for the Cuban people and for the United States” and that the U.S. should not let dollars “prop up a military monopoly that exploits and abuses the citizens of Cuba.”
  • He vowed that sanctions would not be lifted “until all political prisoners are freed, freedoms of assembly and expression are respected, all political parties are legalized, and free and internationally supervised elections are scheduled.”

Demands directed at the Cuban government

Trump often framed his Cuba comments as direct demands to the government in Havana.

  • He called on Cuba to “put an end to the abuse of dissidents” and “release the political prisoners.”
  • He demanded the regime “return the fugitives from American justice,” explicitly naming Joanne Chesimard (Assata Shakur), whom he labeled a “cop-killer.”
  • He also urged Cuba to “hand over the Cuban military criminals” involved in shooting down Brothers to the Rescue planes in the 1990s.

Policy language in his presidency

Beyond speeches, Trump has used formal policy actions and statements to reinforce this stance.

  • In his first term he reversed parts of Obama’s Cuba opening, tightening travel rules and limiting U.S. business with Cuban entities tied to the military and security services.
  • A fact sheet from his administration characterized his approach as “strengthening” U.S. policy and “standing with the people of Cuba in their long quest for justice, liberty and freedom.”
  • In a 2025 memorandum during his second term, Trump imposed an even tougher policy, reinforcing the legal ban on U.S. tourism and bolstering the economic embargo, while barring most financial dealings with organizations controlled by the Cuban military.

Recent tone and “failing nation” framing

More recently, Trump has continued to signal that Cuba could become a renewed focus of U.S. foreign policy.

  • In early 2026, he referred to Cuba as a “failing nation” and indicated it is an issue “we’ll end up talking about,” suggesting potential further actions or pressure.
  • His administration in the mid‑2020s reinstated Cuba on the list of state sponsors of terrorism and expanded sanctions on entities linked to the Cuban state, moves justified publicly as necessary to confront a hostile regime and support Cuban dissidents.

How critics and supporters interpret his words

Trump’s statements on Cuba have sparked intense debate in both the U.S. and the Cuban diaspora community.

  • Supporters, especially in parts of the Cuban‑American community in Florida, see his rhetoric and policies as finally holding the Cuban government accountable and aligning U.S. policy with demands for democracy and human rights.
  • Critics, including Cuban officials, argue that his language—paired with tougher sanctions—amounts to “aggression” and a “blockade” that harms ordinary Cubans more than the leadership, and they have described his measures as “criminal” and an obstacle to the island’s development.

TL;DR: Trump has repeatedly condemned Cuba’s communist government, vowed to cancel “one‑sided” deals, demanded the release of political prisoners and the return of U.S. fugitives, and backed those words with travel restrictions, stronger embargo measures, and terrorism designations, framing everything as solidarity with the Cuban people and pressure on the regime.

Information gathered from public forums or data available on the internet and portrayed here.