Trump signals Cuba reckoning after Iran at Fort Myers rally

By The Conservative Desk (/journals/conservative-desk)

President Donald Trump took a shouted question about Cuba on Oct. 23, 2026, at a midterm rally inside Alico Arena on the Florida Gulf Coast University campus in Fort Myers and answered with American warships. "We'll do a little stopover. Actually, what we're going to do with Cuba is, we're going to come back from Iran. Those beautiful ships will pass Cuba. 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 left the crowd with that image: one ship offshore, hands raised, and the secretary of state sent in to close it. "No, Cuba, he wants to know what about Cuba. Give me a break. Give me a break," Trump said. He added that the vessels might not even need to pause. "We'll have Marco. We don't even have to stop. We could just put him in there and he'll figure it out. He's a great guy."

Moments later Secretary of State Marco Rubio posted on X. "To those who seek to create positive change in Cuba - now is the time." He wrote next: "The disappointment of failed promises, corruption, and the privileged lives of only a few; seize this opportunity to create the change you desire through a discrete partnership with the CIA."

The sequence extended a second-term campaign to force change on the communist government in Havana. In January 2026 the U.S. military seized Venezuelan President Nicolás Maduro in a deadly raid, removing a principal ally of the island. The administration added penalties on nine Cuban state firms in September, aimed at elites, financial channels and resource operations. A U.S. oil and energy blockade in place since January threatens sanctions on any country that supplies fuel to Cuba. Cuba's GDP has shrunk since 2020. About 10 million residents, also cited as 9.4 million, face blackouts, food shortages and inflation. Hundreds of thousands have migrated, many to the United States. A system that cannot keep power on or shelves stocked exports its failure across the Florida Strait. Free enterprise collapses under that model; American communities and taxpayers then absorb the migration and the security cost.

Florida's top prosecutor announced an arrest warrant for Raúl Castro, 95, on state murder charges tied to the 1996 shootdown of two Brothers to the Rescue aircraft. Castro was indicted on related federal charges in May 2026. The warrant treats the killing of civilians flying rescue missions as a present matter of law, not a closed chapter. Cuban President Miguel Díaz-Canel has said the federal indictment has no legal basis and was an attempt to justify the folly of a military aggression against Cuba.

At the U.N. General Assembly in September, Trump labeled Cuba a failed state and said freedom will be coming to Cuba, prompting a walkout by the Cuban delegation. The United States and Cuba clashed again at the United Nations ahead of the annual vote condemning the American embargo, which has lasted more than 60 years. Trump told reporters in the Oval Office earlier that past presidents considered intervening in Cuba but that it looks like he will be the one that does it. He has also said Rubio is deep into negotiations with Cuba, that the countries will make a deal, and that he does not think the military will be needed because Cuba is failing very badly. National sovereignty is concrete from Florida. The United States is entitled to keep the island from becoming a base against American interests and to enforce criminal process against those who ordered civilian deaths.

Trump won 68 percent of the Cuban American vote in Florida in 2024. The Fort Myers appearance was built to lift Rep. Byron Donalds in his race for governor against Democrat David Jolly, in a state where that electorate still decides close contests. Breitbart headlined the speech "Trump Tells Florida of Plans for USA to Topple Cuban Communist Regime." Fox News reported that Rubio urged Cubans to work with the CIA to bring political change to the communist-run island. Both tracked language the president and the secretary used in public.

UN human rights experts have condemned the oil blockade as a violation of international law, and rights advocates say the administration's threats have echoed an imperialist approach. That argument asks Washington to ease pressure while the same leadership retains control. The conditions on the island run the other direction: a contracting economy, chronic blackouts, food shortages, inflation, and rulers who retain privilege while ordinary families carry the cost and leave. Public safety and the border feel that outflow first. The embargo fight returns every year at the U.N.; the blackouts and empty markets do not wait on the next resolution.

Trump has said that Cuba is already failing badly enough that ships may not be required. Rubio's post, timed to the Fort Myers lines about a stopover fifty yards off the coast and hands raised, framed the alternative for Cubans who want change from inside. Cuban Foreign Minister Bruno Rodríguez answered both men by pointing to the shore. "Our coastline is full of beautiful beaches, but there are also razor-sharp limestone spikes, an inhospitable environment for those who make it to our shores with hostile purposes and lust for domination."