The Pentagon has begun quietly drawing up contingency plans for a military operation in Cuba, two people familiar with the matter told USA Today, as President Donald Trump grows increasingly vocal about forcing political change on the island by any means necessary.
The sources, who spoke on condition of anonymity because they were not authorized to discuss the planning publicly, described the preparations as a significant escalation in a months-long pressure campaign against Havana that has already included cutoffs of oil shipments and diplomatic brinkmanship.
The Pentagon declined to confirm the specifics, saying in a statement that it routinely plans for a range of contingencies and stands ready to carry out the president’s orders.
Trump has made little effort to conceal his ambitions. He has spoken publicly about the “honor” of taking Cuba “in some form,” telling reporters he believes he can do “anything I want with it.” In an Oval Office interview with USA Today on Monday, he was more blunt: “We may stop by Cuba after we’re finished with this” — a reference to the ongoing conflict with Iran.
The Cuba planning comes on the heels of the Jan. 3 special operations raid that pulled Nicolas Maduro from his presidential compound in Caracas, killing 32 Cuban military personnel who had been stationed there as a security detail. The operation rattled governments across the Caribbean and Latin America and set off intense speculation in South Florida’s Cuban exile community about what Washington might do next.
But analysts who track U.S.-Cuba relations say the situations are not identical. In the run-ups to operations in both Venezuela and Iran, U.S. officials mounted sustained public arguments about imminent threats to American security. No such case has been made for Cuba.
Behind the military posturing, a fragile diplomatic track has remained open. As recently as March, the two governments had been quietly exploring an economic normalization deal that would have represented a historic shift in relations. Officials on both sides have acknowledged they are still feeling out whether any compromise is possible, though the gaps between their positions remain wide.
Cuban President Miguel Diaz-Canel, for his part, has not moderated his public tone. In a recent interview with Newsweek, he made clear his government would not stand down in the face of a U.S. attack.
“We will battle, we will defend ourselves, and should we fall in battle, to die for the homeland is to live,” Diaz-Canel said.
U.S. military planners have studied the Cuba question on and off since Fidel Castro swept into Havana in 1959, aligned his government with Moscow, and transformed the island into a Cold War flashpoint 90 miles from Florida. The calculus has not changed much in the decades since.
Fonseca said Cuba’s armed forces — underfunded, poorly equipped, and of uncertain loyalty to the current government — would be unlikely to mount sustained resistance against U.S. forces. A military victory, he said, would probably come quickly.
Governing what came after would be another matter entirely.
“This will be a very easy military victory,” Fonseca said, “but a far more difficult political victory.”
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