Trump News: President Eyes Cuba Military Force by 2029
President Donald Trump has put a deadline on one of his longest-running foreign policy ambitions, telling a radio audience on Thursday, November 12, 2026, that he wants to “get Cuba done” before he leaves office and that he would “certainly consider” using military force to do it. The latest trump news out of the White House marks the first time the president has attached a timeline to a possible operation against the island’s communist government, and it caps a year in which Washington has tightened an oil blockade, layered on new sanctions, and watched Cuba’s economy slide deeper into crisis.
The remarks came during a 42-minute telephone interview with conservative radio host Hugh Hewitt on the Salem News Channel, a wide-ranging conversation that also touched on Iran, Israel, and Major League Baseball. But it was the Cuba exchange that carried the most consequence. Hewitt asked the president directly whether he was considering “freeing Cuba” through a military intervention. Trump answered that he wanted the job finished before his term ends in January 2029, and that his administration was “watching it very closely.”
The island Trump described is, in his words, “essentially a failed … place, nation, whatever you wanna call it.” He added that Cuba was “doing very poorly,” and said he would like to act for the sake of Cubans who left the island and settled in the United States after being, as he put it, treated very badly. He also pointed to his own political standing with that community, saying he won the Cuban vote in Florida by a wide margin.
What made Thursday’s comments different was not the threat itself. Trump has repeatedly suggested that the government in Havana could be nearing its end. What changed was the specificity. According to Politico, Thursday was the first time Trump had put a timeline on a possible operation, turning a long-running rhetorical pressure campaign into something with a date attached to it: before he leaves the White House in January 2029.
What Trump Said in the Hugh Hewitt Interview
The exchange unfolded in two parts. First, Hewitt asked Trump whether he was considering freeing Cuba through military intervention. Trump replied: “I want to get Cuba done before I leave.” He added that the administration was watching the island very closely, and described Cuba as a failed nation.
Hewitt then pressed the point, asking whether the president would be comfortable with “a little bit of military force, a week campaign” if that was what it took. Trump answered: “I would certainly consider that, yes.” No order, decision, or operation was announced.
The interview was recorded by telephone and released on Thursday night. It was the same conversation in which Trump mused about becoming Israel’s prime minister and discussed whether he would help prevent a lockout in Major League Baseball. The Cuba remarks, however, were the ones that drew the sharpest attention, carried within hours by Al Jazeera, Newsmax, WION, and other international broadcasters.
Marco Rubio News: The Secretary of State at the Centre of the Cuba Effort
If there is a single figure at the centre of the administration’s Cuba policy, it is Secretary of State Marco Rubio, and Trump made that plain in the interview. “We have a very good, talented guy for Cuba named Marco,” the president said, noting that Rubio’s parents were born in Cuba. “Marco Rubio, his parents are from Cuba as you probably know. And he would love to do that.”
Rubio’s personal history has long shaped his politics on the island. His parents emigrated from Cuba before the revolution, and he has been one of the most consistent voices in American politics calling for pressure on the government in Havana. As secretary of state, he has overseen the administration’s sanctions policy toward Cuba, including the latest round of designations announced by the State Department earlier this month.
That round, announced on November 5, targeted ten people and entities tied to the Cuban government, military, and oil industry under Executive Order 14404, the May 2026 order imposing sanctions on those responsible for repression in Cuba and for threats to United States national security. The designations included Cuban elites, a crude oil shipping network, state-owned import and technical-support entities, and China-based suppliers of the regime’s military forces. Five associated vessels were also identified as blocked property, and the department issued a determination authorising sanctions against any foreign person operating in the electronics, manufacturing, marine, and technology sectors of the Cuban economy.
A Shift From September’s Talk of a Deal
Thursday’s remarks also marked a clear change of tone from where Trump stood only weeks ago. In late September, the president told reporters he expected a deal with Havana and said, “I don’t think we’ll need the military.” That expectation has not been met. Officials from both sides have held talks about the blockade, but Cuba’s foreign minister said in June that there had been “no progress.” The government in Havana, led by President Miguel Diaz-Canel, first secretary of the Communist Party of Cuba, has shown no sign of conceding to American demands, and Cuban officials have said the island is ready for any attack.
The shift in Trump’s language was already visible earlier in the week. On Monday, November 9, the president said Cuba “will fall fairly soon” and that the United States would help the island “on a humanitarian basis.” Three days later, he went further, attaching his own name and his own remaining time in office to the outcome. The progression, from deal-making in September, to prediction on Monday, to a deadline and a willingness to use force on Thursday, suggests a president who has concluded that pressure alone is not moving fast enough.
It also echoes a remark Trump made in March, when he said he believed he would have “the honour of taking Cuba.” That comment came as the island’s power grid collapsed, and it followed the American operation in Venezuela, in which the United States seized Venezuela’s president, Nicolas Maduro, and cut off the Venezuelan oil shipments on which Cuba depended.
The Pressure Campaign: Oil Blockade and Sanctions
The trump administration’s campaign against Cuba has been built on two pillars: cutting off the island’s fuel supply and cutting off its money. Both have intensified sharply in 2026.
The first pillar is the de facto oil blockade imposed in January, after the United States seized Maduro and halted Venezuelan oil shipments to the island. Venezuela had been Cuba’s principal external energy supplier since 2000, and Venezuelan crude still met approximately 40 percent of Cuba’s energy needs in 2025, even after years of decline in Venezuela’s own production. When that supply stopped, the island’s already fragile energy system began to fail.
On January 29, 2026, Trump signed Executive Order 14380, declaring Cuba an “unusual and extraordinary threat” to the United States and a national emergency. The order authorised additional tariffs on goods imported into the United States from any country that directly or indirectly sells or provides oil to Cuba. The message to third countries was unmistakable: supplying fuel to Havana would carry a price in Washington.
The pressure did not stop there. On May 1, 2026, the president signed Executive Order 14404, expanding the sanctions authority to cover foreign companies and financial institutions doing business with the Cuban government. On September 29, the Treasury Department published the Cuba Sanctions Regulations implementing the May order, and a week later federal agents in Miami announced the seizure of 90 biodiesel shipments bound for Cuba. Washington has also sanctioned Cuba’s state oil company, President Diaz-Canel himself, and relatives of former President Raul Castro, and Al Jazeera reported that the United States has issued an arrest warrant for Castro.
Cuba’s Deepening Crisis
Cuba is a nation of about 11 million people, sitting just 90 miles off the Florida coast. Its economy was already in trouble before the current pressure campaign began, weighed down by a centralised system that has struggled to produce enough food, fuel, and foreign currency for years. The loss of Venezuelan oil removed the last reliable external lifeline. Nationwide blackouts have become routine, the power grid has collapsed repeatedly, and fuel and food shortages have deepened, a humanitarian crisis the administration’s critics say punishes ordinary Cubans more than it pressures their government.
Trump’s own framing on Monday, that the United States would help Cuba “on a humanitarian basis” once the government falls, suggests the administration is aware of that criticism and is trying to answer it in advance. The offer of humanitarian help after a collapse is, in effect, a promise that American pressure has a humanitarian endpoint.
The Cuban government, for its part, has not signalled any willingness to negotiate its own exit. Diaz-Canel remains in place, the Communist Party remains in control, and the island’s leadership has said repeatedly that it will resist. The talks between the two sides produced no progress by June, and there has been no public indication of a breakthrough since. Cuba has also accused the United States of threatening other countries ahead of a United Nations vote on the American embargo, a vote that has become an annual ritual of near-unanimous international opposition to the blockade.
Pentagon News: No Rehearsals for an Invasion, for Now
For all the force of Trump’s words, the military picture remains unclear. In March, the head of United States Southern Command told senators that American troops were not rehearsing for an invasion of Cuba, a direct answer to lawmakers who wanted to know whether the Pentagon was preparing for war with the island.
No new statement from the Pentagon has followed Thursday’s interview, and there has been no announcement of troop movements, exercises, or planning directed at Cuba. The absence of visible military preparation does not mean none exists, but it does mean that Trump’s remarks, for now, stand alone as a statement of intent rather than the public face of an operation already under way.
The gap between rhetoric and readiness is a familiar feature of Trump’s approach to foreign policy. He has repeatedly used the threat of force as leverage, sometimes following through, as in Venezuela and in the campaign against Iran, and sometimes using the threat itself as the instrument. The question now is which pattern Cuba follows, and whether the deadline Trump has set for himself, January 2029, becomes a real planning horizon for the Pentagon or remains a political promise made on a radio show.
What Happens Next
The immediate question is whether Thursday’s interview produces any visible follow-through. The White House has not announced new sanctions, new military movements, or new diplomatic initiatives in the hours since the interview aired. The State Department’s most recent designations, announced earlier this month, remain the latest concrete step, and the oil blockade continues to operate as it has since January. The same interview also carried a warning about Iran, covered in a separate report, in which Trump said he would not hesitate to resume strikes if Tehran attacked American allies or ships.
The next markers to watch are practical ones. Any change in the posture of United States Southern Command, any new round of sanctions designations, any statement from the Pentagon or from Rubio himself, and any response from Havana will show whether the president’s words are being translated into action. So will the state of Cuba’s power grid and fuel supply, which remain the most immediate measure of how much pressure the blockade is exerting.
The political calendar matters too. Trump has less than three years left in office, and the deadline he set for himself is the end of his term. That leaves time for negotiation, for escalation, or for the status quo to persist. What Thursday’s interview removed was ambiguity about the president’s ambition. He wants Cuba done, he wants it done before he leaves, and he is willing to consider force to make it happen. The rest, for now, is a question of what follows the words.
Source: CNBC