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Secretary Rubio Engages in High-Level Talks with Cuban Regime, Claims Trump

Friday, February 27, 2026 by Ethan Navarro

On Friday, U.S. President Donald Trump revealed that Secretary of State Marco Rubio is engaged in "high-level" discussions with the Cuban regime. This statement came in response to a question about the possibility of a regime change occurring in Cuba "soon."

Trump characterized Cuba as a "failing" nation facing a "very bad" situation. He noted, "Marco Rubio is handling it and is doing so at a very high level," without specifying the individuals involved or the locations of these discussions. Trump also alluded to the potential for a "friendly takeover" of the nation.

Speaking with reporters outside the White House, Trump reiterated his assessment of Cuba's internal conditions. "Cuba, right now, is a nation that's failing," he stated, recalling that talk of change on the island has been ongoing "since I was a little boy," indicating that "everyone wanted a change."

Building on this point, Trump asserted, "I can see it happening," referencing Rubio's alleged dealings with the Cuban government. He further claimed that Cuba is experiencing a dire shortage of resources: "They have no money, no oil, no food," he said, describing it as "a nation in serious trouble."

In light of this scenario, Trump mentioned that Cuba "wants our help," though he did not detail the type of assistance requested or the conditions involved.

Behind Closed Doors: U.S.-Cuba Discussions

On Wednesday, U.S. officials close to Secretary of State Marco Rubio held a discreet meeting with Raúl Guillermo Rodríguez Castro, grandson of Raúl Castro and an influential figure in Cuban power circles. This encounter occurred on the sidelines of the CARICOM leaders' summit in the Caribbean.

According to multiple sources cited by the Miami Herald, the meeting took place in a hotel near the 50th Regular Meeting of the Conference of Heads of Government of the Caribbean Community (CARICOM). Rodríguez Castro, known in Cuba as "El Cangrejo," reportedly traveled to Saint Kitts with a protocol official and left the island the same day.

It remains unclear whether Rubio himself participated in the talks, though his presence at the summit and his team's engagement with Castro's grandson suggest that the Trump administration considers him a key interlocutor in the ongoing dialogue with Havana.

While Rodríguez Castro holds no formal government or Communist Party position, he is regarded as the closest advisor and confidant of Raúl Castro. He is also linked to the oversight of GAESA, a military conglomerate controlling significant sectors of the Cuban economy.

A Caribbean diplomat mentioned that in private talks with regional leaders, Rubio hinted that negotiations with the Cuban government are "very advanced," but clarified that Washington does not wish to extend the regime's lifespan.

Insights into U.S.-Cuba Relations

What did Trump say about the current situation in Cuba?

Trump described Cuba as a "failing" nation going through a "very bad" situation, lacking essential resources like money, oil, and food.

Who is Raúl Guillermo Rodríguez Castro?

Raúl Guillermo Rodríguez Castro, known as "El Cangrejo," is the grandson of Raúl Castro and an influential figure in Cuba, though he holds no formal government position.

Are the U.S.-Cuba negotiations progressing?

According to sources, negotiations are "very advanced," but the U.S. does not intend to prolong the current Cuban regime.

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