President Trump declared Saturday morning that Cuba "will be the next nation" he targets once the conflict with Iran concludes, telling an audience at the Shield of the Americans Summits in Florida that Secretary of State Marco Rubio "is in talks with Cuba" and that a deal could be reached "very easily."

The remarks came during a week in which tensions between Washington and Havana spiked sharply, following a Cuban Coast Guard shooting that killed four people aboard a Florida-registered speedboat and a joint U.S.-Israel military operation against Iran that has reshaped the geopolitical landscape at breakneck speed.

Trump did not mince words about the state of the communist island.

"Cuba is at the end of the line, they're very much at the end of the line. They have no money, they have no oil. They have a bad philosophy, they have a bad regime."

According to the Daily Mail, he promised the island's 11 million people a "great new life" and said the country is "in its last moments of life the way it is." Then he floated a phrase that will echo in Havana for weeks: "Maybe we'll have a friendly takeover of Cuba."

A Regime Running on Fumes

The timeline tells the story. Cuba relied heavily on Venezuelan oil. After the January 3 U.S. strike on Venezuela, which resulted in the capture of President Nicolás Maduro, the Trump administration shut off Cuba from that supply. The island was already suffering power outages lasting up to 15 hours per day, according to USA Today. An 11-million-person nation plunged into darkness daily, propped up by nothing but ideology and inertia.

Then, in late February, the administration allowed U.S. petroleum products to be sold directly to Cuba, breaking the 1960 embargo that bans most American exports to the island. The move was strategic, not charitable. When your neighbor's house is collapsing, and you're the only one selling lumber, you don't need a battering ram. You need a doorbell.

This is leverage applied with precision. Cut the old lifeline, then extend a new one on American terms. Cuba's President Miguel Diaz-Canel has promised reform before, with nothing to show for it. The question now is whether he has any choice left.

The Speedboat Incident

Tensions sharpened Wednesday morning when a Cuban Coast Guard member killed four people aboard a Florida-registered speedboat that had crossed into Cuban waters. Six more were injured. The Cuban Embassy released a statement on X claiming the vessel was intercepted approximately one nautical mile northeast of the El Pino channel in the Villa Clara province.

"In the face of current challenges, Cuba reaffirms its determination to protect its territorial waters, based on the principle that national defense is a fundamental pillar of the Cuban State in safeguarding its sovereignty and ensuring stability in the region."

The nationalities of those killed and injured remain unknown. What is known is that a communist regime with no functioning power grid, no oil supply, and no economic future still found the resources to shoot at a speedboat. Priorities.

Rubio responded directly. His message was blunt: "Cuba needs to change, it needs to change dramatically." Reports indicate he is already in talks with former leader Raúl Castro's grandson, suggesting the administration is working multiple channels simultaneously.

Iran First, Then the Caribbean

Trump made clear that Cuba would not move to the forefront of American policy until after the Iran situation is resolved. That situation has escalated rapidly. In just one week:

• A joint U.S.-Israel military operation took out Supreme Leader Ayatollah Ali Khamenei
• Iran's Assembly of Experts and senior Islamic Revolutionary Guard Corps members have been tasked with naming a successor
• Trump called the rumored successor, Khamenei's son Mojitaba, "incompetent" and a "lightweight."

On Saturday, Trump posted on Truth Social that areas and groups "not considered for targeting up until this moment in time" were now under serious consideration for "destruction and certain death, because of Iran's bad behavior." The language leaves no room for misinterpretation.

A National Intelligence Council report completed just a week before the operation had apparently raised doubts. The NIC bridges 18 intelligence agencies. Trump moved forward anyway. The results speak louder than pre-operation hand-wringing.

What Cuba is Actually Facing

Strip away the Cold War nostalgia that the American left occasionally indulges in, the romanticized revolutionary imagery, the Che Guevara t-shirts worn by people who would last about four minutes under an actual communist regime, and what you see in Cuba is simple: a failed state running out of time.

No oil. No money. No reliable electricity. A population enduring conditions that would trigger emergency humanitarian declarations if they occurred anywhere the international community actually cared about. The 1960 embargo, still technically in place, has become almost beside the point. Cuba's collapse is not an American policy outcome. It is the inevitable result of six decades of communist governance.

Trump's approach combines economic pressure with an open hand. The petroleum sales allowance creates dependency on American goodwill. The diplomatic channel through Rubio signals that Washington prefers negotiation. The "friendly takeover" language signals that Washington also has other options.

This is not the Obama-era approach of granting concessions and hoping the regime modernizes out of gratitude. That experiment ran its course and produced nothing. This is transactional diplomacy backed by demonstrated willingness to act, with Venezuela and Iran serving as very recent, very visible proof of concept.

The Clock is Ticking in Havana

Cuba's leadership faces a calculation that gets worse with every passing day. The oil is gone. The patron state that supplied it has fallen. The only country offering fuel wants a dramatic change in return. And the president making that demand just removed a supreme leader from power in the Middle East.

Trump told the Florida audience that as a boy, he'd hear about Cuba. It's been a disaster for as long as anyone can remember. He's right. The difference now is that the disaster is reaching its terminal phase, and the man in the Oval Office has no interest in managing decline. He's offering a deal.

Havana would be wise to take the call.