“Brief Exchange”: Top U.S., Cuban Military Leaders Meet At Edge Of Guantanamo Base

Three weeks after CIA Director John Ratcliffe met with officials in Havana, reopening a political backchannel between Washington and the Cuban government, a rare military-to-military meeting unfolded at the edge of the U.S. naval base at Guantanamo Bay.

U.S. Southern Command wrote on X that Marine Gen. Francis Donovan, head of U.S. Southern Command, met with Cuban Gen. Roberto Legrá Sotolongo and other officers at the perimeter of Naval Station Guantanamo Bay for what SOUTHCOM described as a “brief exchange on operational security matters.”

#SOUTHCOM Commander Gen. Francis L. Donovan met with Army Corps General, Gen. Roberto Legrá Sotolongo, First Deputy Minister of the Chief of the General Staff, and other senior leaders from the Cuban military today at the perimeter of Naval Station Guantanamo Bay, Cuba, for a… pic.twitter.com/V4Fau3HxSo

— U.S. Southern Command (@Southcom) May 29, 2026

SOUTHCOM did not elaborate on the brief exchange between top U.S. military brass in the region and Cuban generals. No statement was issued by the U.S. Embassy in Havana, leaving the meeting framed as yet another signal that U.S.-Cuba talks are strengthening.  

In mid-May, CIA Director John Ratcliffe held high-level talks with Cuba’s Interior Minister, the head of Cuban intelligence, and Raúl Castro’s grandson, Raulito Rodríguez Castro.

Havana, Cuba pic.twitter.com/7S7TtJPyf5

— CIA (@CIA) May 14, 2026

Havana’s communist government released a statement noting that the meeting “took place Thursday, May 14, against a backdrop of complex bilateral relations.”

AP noted that Cuban officials presented a report to Ratcliffe and his team, claiming to demonstrate that the communist-run island poses no threat to U.S. national security.

Meanwhile…

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Increased back channeling has come amid a sharp escalation in U.S.-Cuba tensions. The Trump administration has been pressing Havana for sweeping economic and political reforms, while the U.S. naval blockade on fuel shipments remains in place.

President Trump has repeatedly warned Havana about military intervention. The Justice Department last week unsealed an indictment against former Cuban President Raúl Castro and five others of the communist regime.

Also, the Treasury Department subpoenaed far-left influencer Hasan Piker over his trip to Cuba. He and CCP-aligned NGOs that went to Cuba are being investigated by officials to determine if they violated U.S. sanctions and laws.