President Donald Trump announced this Friday, during a rally in Fort Myers, Florida, that once U.S. military operations in Iran are concluded, he will send Secretary of State Marco Rubio to Cuba to "seal the deal" with the Havana regime, in a statement that the official White House account shared on the social network X.
"We are going to return from Iran, those beautiful ships will pass by Cuba. We will make one of them stop about 50 yards from the shore. They will raise their hands, and then we will send Rubio to finish the job," Trump said before a crowd that responded with a thunderous ovation, according to a post by Rapid Response 47, the White House's rapid response account.
The statement explicitly links two geopolitical fronts: Trump presented Cuba as a pending issue that Washington will address once the military resources deployed in the Middle East become available, turning the show of naval strength into a prelude to diplomatic efforts led by Rubio.
The event at the Alico Arena of Florida Gulf Coast University aimed to support Republican candidates in the upcoming midterm elections on November 3, including Byron Donalds, a candidate for governor of Florida, a state with a large community of Cuban exiles.
This Friday, Marco Rubio also published a message on his official X account that marks a turning point in Washington's pressure on Havana: a public and explicit invitation to those who wish to change Cuba to collaborate discreetly with the Central Intelligence Agency.
"For those looking to create positive change in Cuba: now is the time. The disappointment over unfulfilled promises, corruption, and the privileged lives of a few; seize this opportunity to bring about the change you desire through discreet collaboration with the CIA," he wrote on his X profile.
Agreement with Cuba?
Since February 2026, President Trump has maintained a consistent discourse about the possibility of an agreement with the Cuban regime.
First, he stated that Rubio was having discussions "at a very high level" with the government, without identifying the parties involved or any specific objectives.
In March, at the Shield of the Americas summit in Miami, he asserted that Cuba "wanted to negotiate" and that an agreement could be reached "very easily."
In September, before the UN General Assembly, Trump was back at it: he declared that Rubio was "deeply involved" in negotiations with Cuba and that he believed his Secretary of State had "figured out" the issue.
However, the reality on the ground is far from that optimism. According to an investigation by The Atlantic published in October, the indirect contacts between Rubio and Raúl Guillermo Rodríguez Castro —the grandson of Raúl Castro, known as "El Cangrejo"— have stalled after Washington demanded the removal of Miguel Díaz-Canel as a condition to move forward.
Havana also rejected a U.S. proposal of 100 million dollars in aid —60 million in fuel— linked to the privatization of the Cuban energy industry, a condition that the regime deemed unacceptable.
The Cuban government, for its part, has been careful to temper expectations. Foreign Minister Bruno Rodríguez Parrilla acknowledged only "some episodes of conversation" with U.S. officials.
The Cuban chargé d'affaires in Washington, Lianys Torres Rivera, clarified on October 6 that the contacts —which included meetings, calls, and WhatsApp messages— did not constitute formal negotiations.
Days later, the diplomat Tanieris Diéguez confirmed the exchanges but ruled out any progress towards formal dialogue and refused to discuss the political structure of the regime.
While diplomacy remains at a standstill, the economic pressure on Cuba has not eased.
The Trump administration allegedly intercepted at least seven tankers carrying fuel intended for the island, resulting in an estimated reduction of between 80% and 90% of Cuba's crude oil imports, according to data published in early May.
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