.png "Global Insight")
At a campaign rally in Fort Myers, Florida, on Friday, October 23, 2026, President Donald Trump revived an idea he had not mentioned in months: American warships returning from the Middle East, he said, could make "a little stopover" off Cuba on their way home. "We'll take care of Cuba on our way back from Iran," Trump told the crowd. "We'll have one of them stop about 50 yards off the coast. They'll raise up their hands, and then we're going to send Marco Rubio in to finish up the deal." Within hours, Secretary of State Marco Rubio had posted his own message to Cubans, and the CIA had amplified it. Havana answered with defiance. The question now is whether this is campaign rhetoric, a genuine pressure campaign — or both.
What Trump and Rubio actually said
Trump's remarks came in response to a shouted question from the crowd about Cuba, according to reports from the Associated Press. He has floated the warship idea before, earlier this year, and has previously suggested Cuba would be "next" after Venezuela — where US forces seized then-president Nicolas Maduro in a deadly raid in January. He has also, at other moments, predicted a deal with Cuba without military action. The rally version was the harder-edged one: a warship parked off the coast, then Rubio sent in to close a deal.
Rubio's message was more direct, and more unusual. "To those who seek to create positive change in Cuba — now is the time," he posted on X. The CIA replied to his post with a similar message, urging Cubans seeking change to pursue "a discreet partnership with the CIA" and citing "the disappointment of failed promises, the corruption, and the privileged lives of a few." A secretary of state publicly inviting citizens of another country to work discreetly with an intelligence agency is not normal diplomacy — and that is precisely why it drew attention.
Why Cuba is under pressure right now
The threats land on an island already under severe strain. A US-imposed oil blockade implemented earlier this year has deepened fuel shortages and blackouts, worsened by failing infrastructure, according to reports from The Hindu. Washington has maintained an embargo on Cuba for more than 60 years, and the Trump administration has stepped up pressure since the Maduro raid, including new penalties targeting nine state-owned companies in construction, mining and metals, and tighter enforcement of restrictions on Americans doing business with Cuban state-controlled enterprises.
Cuba's government says it will not be intimidated. Foreign Minister Bruno Rodriguez wrote on X that Cuba rejects "every threat related to US ambitions toward Cuba," warning that its coastline, while full of beaches, is also "an inhospitable environment for those who make it to our shores with hostile purposes." Cuba's foreign minister told the UN General Assembly last month that Cuba would always be open to dialogue with Washington — a door left open even as the rhetoric sharpens.
What could actually happen next
Three paths are visible, and they are very different. The first is a negotiated opening: Trump himself has predicted an agreement, and the administration's stated goal is a change in Cuba's communist government and governance model, which Rubio argues is the precondition for investment. The second is continued economic strangulation: more sanctions, tighter oil flows and more public encouragement of internal dissent, without any shot fired. The third — the one the rally language gestures at — is some form of military intimidation or intervention, which Trump has not ruled out, saying the US "may do another little Epic Fury, or they'll agree."
For now, the concrete actions are economic and rhetorical, not military. No warship has been ordered to Cuba's coast, and no operation has been announced. But the combination — a president talking about warships, a secretary of state talking about discreet CIA partnerships, and an island running short of fuel — is why this story matters beyond one rally. It is also why it should be read carefully: rally applause lines are not orders, but they do signal intent. The next test will be whether the pressure produces talks, hardship, or something harder to control.
For the wider regional picture, see our report on the US diplomat pullback as Iran plots warnings grow. Sources for this report include the Associated Press and USA Today.