During a rally in Fort Myers, Florida, President Donald Trump revealed plans on Friday to dispatch Secretary of State Marco Rubio to Cuba for negotiations with the Havana regime. This announcement came after U.S. military operations in Iran reach their conclusion, as shared by the official White House account on the social platform X.
Trump addressed the crowd, saying, “Once we're back from Iran, our magnificent ships will pass by Cuba. We'll have one of them halt just about 50 yards from the coast. They'll raise their hands, and then we'll send in Rubio to wrap things up.” This statement was met with enthusiastic applause from the audience, according to Rapid Response 47, the White House's swift response account.
This bold declaration ties together two significant geopolitical issues. Trump framed Cuba as an unresolved matter that the United States would address once military resources from the Middle East are reallocated, positioning the naval display as a precursor to Rubio-led diplomatic efforts.
The event at Florida Gulf Coast University's Alico Arena aimed to bolster support for Republican candidates leading up to the midterm elections on November 3, including Byron Donalds, a gubernatorial hopeful in Florida, a state with a large Cuban exile community.
In a related move, Marco Rubio took to his official X account on the same day to call for discreet collaboration with the Central Intelligence Agency from those desiring change in Cuba. “To those seeking a positive transformation in Cuba: now is the time. Discontent with broken promises, corruption, and the privileged lives of a few; seize this opportunity to drive change through discreet cooperation with the CIA,” he posted.
Ongoing Talks with Cuba?
Since February 2026, President Trump has consistently spoken about the potential for a deal with the Cuban regime. Initially, he claimed that Rubio was engaged in discussions at a “very high level” with Cuban officials, without specifying the key figures or goals involved.
By March, during the Summit of the Americas in Miami, Trump noted that Cuba “wanted to negotiate” and that reaching an agreement could be “very easy.” In September, at the United Nations General Assembly, Trump reiterated that Rubio was “deeply involved” in negotiations with Cuba and believed his Secretary of State had “cracked” the matter.
However, the reality seems less optimistic. An investigation by The Atlantic in October highlighted that indirect contacts between Rubio and Raúl Guillermo Rodríguez Castro—known as “El Cangrejo”—had stalled following Washington's demand for the departure of Miguel Díaz-Canel as a condition for further progress.
Additionally, Cuba rejected a U.S. offer of $100 million in aid—$60 million of which was for fuel—contingent on the privatization of Cuba's energy industry, a stipulation deemed unacceptable by the Cuban regime.
On the Cuban side, officials have tempered expectations. Foreign Minister Bruno Rodríguez Parrilla acknowledged only “some episodes of conversation” with U.S. officials. Lianys Torres Rivera, Cuba’s chargé d'affaires in Washington, clarified on October 6 that these interactions—comprising meetings, calls, and WhatsApp messages—did not amount to formal negotiations.
Soon after, diplomat Tanieris Diéguez confirmed these exchanges but denied any progress towards formal dialogue and refused to discuss changes to the political structure of the regime.
Amidst diplomatic deadlock, economic pressures on Cuba persist. The Trump administration reportedly intercepted at least seven tankers carrying fuel intended for Cuba, leading to an estimated 80% to 90% reduction in the island's crude oil imports, based on data released in early May.
Insights into U.S.-Cuba Relations
What is President Trump's plan for Cuba?
President Trump intends to send Secretary of State Marco Rubio to Cuba to negotiate with the regime after concluding U.S. military operations in Iran.
How has the Cuban government reacted to U.S. proposals?
The Cuban government has cautiously downplayed expectations, acknowledging only limited conversations with U.S. officials and rejecting proposals they find unacceptable.
Has there been any progress in U.S.-Cuba negotiations?
Despite claims of ongoing negotiations, no significant progress has been made due to differing conditions and expectations from both sides.