Trump Tells Florida Rally U.S. Warships Will Stop 50 Yards Off Cuba on the Way Home From Iran

President Donald Trump told a campaign rally in Fort Myers, Florida, on Friday, Oct. 23, that U.S. warships coming home from the Iran war will make a stop at Cuba.

"We'll do a little stopover," Trump said. "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."

He was answering a question shouted from the crowd. Trump first floated the idea earlier this year and had not raised it publicly in recent months.

Rubio follows with a CIA message

Moments after Trump spoke, Secretary of State Marco Rubio posted on social media that "now is the time" for action on Cuba. He addressed the post "to those who seek to create positive change" and urged them "to seize this opportunity to create the change you desire through a discrete partnership with the CIA."

Rubio had said little about Cuba in public for several weeks. His last extended comments came in a Sept. 29 interview with Fox News host Sean Hannity.

"The truth is Cuba has already fallen," Rubio said then. "It doesn't have a functional economy and it's governed by people who continue to preach about some revolution that has been dead for 20 years that's never worked." He did not mention any CIA operation in that interview.

How the pressure built

The rally comments follow a months-long escalation. In May, Trump and Rubio raised the prospect of U.S. military intervention after the administration announced criminal charges against former Cuban leader Raúl Castro. Trump told reporters in the Oval Office that previous presidents had considered intervening for decades but "it looks like I'll be the one that does it."

Rubio said then that Cuba has been a national security threat for years because of its ties to U.S. adversaries. He said the administration wants to resolve differences peacefully, but he put the likelihood of a diplomatic resolution with the current government at "not high."

In September, Trump called Cuba a "failed state" at the UN General Assembly and said "freedom will be coming to Cuba." The Cuban delegation walked out. Trump has said openly that his goal is to change Cuba's government. Earlier this year, the U.S. also ousted the leader of Venezuela.

A U.S.-imposed oil blockade is already squeezing the island, which is dealing with fuel shortages and blackouts made worse by failing infrastructure. UN human rights experts have condemned the blockade as a violation of international law. The administration's position, as Rubio has stated it, is that the Cuban government is a security threat and an economic failure.

The political backdrop

Florida has a large Cuban American electorate, and Trump won 68% of that vote in the state in 2024. The rally was meant to boost Rep. Byron Donalds, the Republican running for governor against Democrat David Jolly.

The midterms are Nov. 3. Voters have told pollsters they are worried about what the Iran war has done to prices, from gas to groceries. Trump spent 90 minutes at the podium, much of it on other topics. He said he plans to spend $250 million to hire at least 5,000 nurses for elder care facilities.

He also repeated that more military action against Iran may lie ahead. He has long forecast that the war would wind down, but it has not.

What is unsettled

The Cuba plan has a built-in dependency. Warships cannot come home from a war that is not over, and Trump did not say when that might happen. He also did not say what the "deal" Rubio would finish would contain.

What Rubio's CIA message was meant to produce is also unspecified. Neither he nor Trump has said who the "partnership" is aimed at or what it would involve.

One thing is on the calendar. Voters in Florida and across the country decide the midterms in 11 days, and the Iran war's effect on prices is among the concerns they have cited.