Top U.S. general in Caribbean meets with Cuban military leaders near Guantanamo Bay as tensions simmer

May 30, 2026
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The head of the U.S. military’s Southern Command met with top Cuban military officials Friday at the edge of the American naval base at Guantanamo Bay, as President Trump heaps pressure on Cuba and does not rule out military action.

Gen. Francis Donovan, commander of SOUTHCOM, held a “brief exchange on operational security matters” with Cuban Gen. Roberto Legrá Sotolongo, the U.S. military said on X.

Cuba’s defense ministry confirmed the meeting on X and called it “positive,” with the two sides discussing “topics of interest to both parties.”

In the past, American and Cuban officers have periodically held “fence-line meetings” to discuss security at Guantanamo Bay, a constant point of tension between the two countries because Cuba regards the naval station — which predates the Castro government — as illegal.

But it’s far rarer for the head of SOUTHCOM, which oversees U.S. forces in the Caribbean and most of Latin America, to meet with senior Cuban officials.

It’s the latest high-level contact between the United States and Cuba, following visits to Havana by CIA Director John Ratcliffe two weeks ago and State Department diplomats last month.

In recent months, the Trump administration has put intense pressure on Cuba, which has frustrated U.S. presidents for decades. The island nation has faced severe energy shortages after Mr. Trump threatened tariffs on any country that exports oil to Cuba. The U.S. has also tightened sanctions and criminally charged 94-year-old former Cuban leader Raúl Castro. 

Secretary of State Marco Rubio has said Cuba needs to make sweeping economic and political reforms. When Ratcliffe visited the island to meet with Raúl Castro’s influential grandson, he conveyed the message that the U.S. could expand economic and security cooperation with Cuba if it made “fundamental changes,” a CIA official told CBS News. 

Meanwhile, Mr. Trump has dangled the possibility of military action, saying he’s interested in “taking Cuba in some form” and warning after the war with Iran, “Cuba’s going to be next.” Still, he said earlier this month, he didn’t think escalation would be necessary.

The U.S. intelligence community has analyzed how Cuba might respond to American military action and what kind of blowback may follow, CBS News has previously reported. Among the concerns: CBS News has confirmed that Cuba has acquired attack drones. Rubio has also raised worries about Cuba hosting Chinese and Russian spy facilities.

Cuban President Miguel Díaz-Canel denied Havana poses any military threat to the U.S., but warned that a U.S. assault would cause a “bloodbath.”

During Ratcliffe’s meeting in Havana earlier this month, he brought along a striking guest: One of the paramilitary operators who was involved in a mission to capture Cuba’s onetime ally, former Venezuelan leader Nicolás Maduro, in an operation that killed dozens of Cubans.

He made a point of introducing the paramilitary leader to the Cubans as the one who killed their people in Venezuela, several sources told CBS News earlier this month.

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