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Trump Floats Military Operation in Cuba, Sets 2029 Deadline

President Trump told conservative radio host Hugh Hewitt that he is considering using military force to take over Cuba before his term ends in 2029, with Secretary of State Marco Rubio playing a key role. The remark marks the first time Trump has attached a timeline to a potential intervention in the communist-run island.

Trump Floats Military Operation in Cuba, Sets 2029 Deadline

President Donald Trump said Thursday that he is weighing a military operation in Cuba and wants to complete it before leaving office in 2029, the first time he has set a timeline for potential intervention in the communist-run island nation.

“I want to get Cuba done before I leave,” Trump told conservative radio host Hugh Hewitt, who asked whether the president was considering “freeing Cuba” through military action. Trump said Secretary of State Marco Rubio would play a central role in any effort.

“We have a very good, talented guy for Cuba named Marco, because Marco’s parents are from ... Cuba, as you probably know, and he would love to do that,” Trump said.

The comments, made during a Thursday interview, escalate Trump’s repeated rhetoric about deposing Cuba’s government by adding a specific deadline for the first time. Trump has previously spoken broadly about wanting to see the end of Cuba’s communist system but had not tied a potential military operation to his departure from the White House.

The president’s remarks raise significant questions about U.S. foreign policy toward Cuba, a nation of 11 million people just 90 miles off the Florida coast. A military intervention would mark a dramatic break from decades of U.S. policy that has relied primarily on economic sanctions and diplomatic pressure. It would also carry enormous risks for regional stability and could draw sharp opposition from international allies and members of Congress.

Rubio, whose parents fled Cuba before the 1959 revolution, has long been a vocal critic of the island’s government. As secretary of state, he would be positioned to shape any Cuba strategy. Trump’s comments suggest Rubio would be a key architect of an intervention if the administration moves forward.

The White House did not immediately provide details on what a military operation might entail or whether any planning has begun. The Pentagon declined to comment.

Trump’s remarks come as his administration continues to reshape U.S. foreign policy in Latin America, often with a focus on leftist governments. During his first term, Trump rolled back the Obama-era opening with Cuba, tightening travel and trade restrictions. In his second term, he has signaled a more aggressive posture toward the island.

The timeline Trump offered—before he leaves office in January 2029—leaves less than three years for any potential operation. It remains unclear whether the president’s comments reflect a serious policy shift or are primarily rhetorical, a pattern that has sometimes followed his public statements about foreign adversaries.

Critics of a military approach argue that an invasion would be costly, could trigger a humanitarian crisis, and would likely inflame anti-American sentiment across Latin America. Supporters of a harder line say decades of sanctions have failed to dislodge Cuba’s government and that more pressure is needed.

For Cuban-American communities in Florida and elsewhere, the president’s comments are likely to resonate. Many have long supported a tougher stance against the Cuban government, though views on military intervention are more divided.

The remarks also come amid broader questions about the scope of presidential war powers. Any sustained military operation would likely require congressional authorization under the War Powers Resolution, though presidents have sometimes acted without it in limited strikes.

Trump’s interview with Hewitt is the latest in a series of media appearances in which he has discussed foreign policy in informal settings. The president has frequently used friendly radio and television hosts to float policy ideas before formal announcements.

It remains to be seen whether the administration will take concrete steps toward a Cuba operation or whether the president’s comments will remain a rhetorical flourish. For now, the statement has injected new uncertainty into U.S.-Cuba relations and raised the stakes for a region already grappling with political and economic instability.

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