US General Meets Cuban Military at Guantanamo as Fuel Crisis Forces Havana Toward Negotiation
Rare military dialogue signals tactical shift from Trump's own hardline playbook as oil blockade bites and Beijing positions to preserve influence.
General Francis Donovan, head of U.S. Southern Command, met with senior Cuban military officials at the perimeter of Guantanamo Bay on 29 May, marking the highest-level direct military contact since Washington imposed a fuel blockade that has depleted Cuba’s oil and diesel reserves.
The meeting with Cuban General Roberto Legra Sotolongo focused on operational security matters, according to Reuters. It follows a rare May visit by CIA Director John Ratcliffe to Havana, suggesting the Trump Administration is testing a pressure-plus-negotiation approach after four months of maximum economic coercion. The shift comes as Cuba runs out of fuel, political prisoners are released, and China moves to fill the vacuum left by Venezuela’s collapse.
Blockade Architecture
Trump signed an executive order on 29 January threatening tariffs on any country supplying oil to Cuba, per congressional briefing. The order took effect the following day. By 14 May, Cuban Minister of Energy and Mines Vincent De La O’levy acknowledged the island had exhausted its oil and diesel reserves. The blockade eliminated Cuba’s principal supplier: the U.S. military captured Venezuelan President Nicolás Maduro on 3 January, ending Caracas’s subsidised shipments to Havana.
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The strategy mirrors the Venezuela playbook: impose crippling Sanctions, offer humanitarian relief, extract concessions. But structural differences limit transferability. “Cuba, like Iran, is a very different country than Venezuela,” Brian Finucane, senior adviser at the International Crisis Group, told the Washington Times on 23 May. Cuba’s military remains unified, its population more tolerant of hardship, and its regime less penetrated by outside actors.
Reversal of Prior Policy
The military dialogue represents a tactical pivot from Trump’s own 2017-2020 approach, when he reversed President Obama’s diplomatic opening by strengthening the embargo, closing the U.S. Embassy in Havana, and restricting travel. The current escalation—which began with Trump’s second-term inauguration in January 2025—has been paired with preliminary diplomatic contact that would have been unthinkable during the first term.
Cuba agreed to release 51 political prisoners in March, with over 2,000 freed by 3 April, according to crisis timelines. Washington offered $100 million in humanitarian aid including food and medical supplies in May. President Miguel Díaz-Canel publicly acknowledged talks were underway on 13 March, though Cuban Ambassador to the UN Ernesto Soberón Guzmán ruled out “negotiations on issues like regime change or removing the president.”
“If it developed into a physical security threat to the U.S. embassy or the base at Gitmo, we would put U.S. troops to defend American lives.”
— General Francis Donovan, Head of U.S. Southern Command
The administration reportedly wants Díaz-Canel to leave the country, permit American investment, release additional political prisoners, and purge former Castro officials. Havana has acceded to Cuban American investment but resists broader regime dismantlement. On 20 May, Washington formally charged former President Raúl Castro with four counts of murder for the 1996 downing of civilian aircraft, signaling that hardliners retain influence even as dialogue proceeds.
Geopolitical Competition
China and Russia are positioning to preserve leverage in any post-Díaz-Canel scenario. Beijing sent $80 million in financial assistance this year and is constructing 55 solar parks, per Peoples Dispatch. Trade ties between China and Cuba surpassed $1.3 billion as of 2021, making Beijing Cuba’s dominant economic partner.
“We deeply understand that true friendship is revealed in times of greatest need,” Chinese Ambassador Hua Xin said in January. “[China] has always been Cuba’s most steadfast partner.” Moscow has reaffirmed support but lacks the economic resources to match Beijing’s involvement. Russia’s role has declined to symbolic military cooperation and intelligence sharing.
U.S. officials cite China and Russia’s increasing influence—particularly intelligence and logistics cooperation—as a motivation for regime change by year-end. But Washington’s leverage is constrained. Cuba’s Foreign Minister Bruno Rodriguez warned that “any military action would lead to a ‘bloodbath’ in which thousands of Cubans and Americans would die.” Díaz-Canel told supporters: “We are ready, and I say it with a profound conviction that I have shared with my family, to give our lives for the revolution.”
What to Watch
The Guantanamo meeting establishes a military deconfliction channel that could prevent miscalculation as economic pressure intensifies. Whether it leads to broader negotiation depends on three variables: Havana’s willingness to sacrifice Díaz-Canel, Washington’s tolerance for partial concessions, and Beijing’s ability to sustain Cuba through winter. If dialogue stalls, the administration faces a choice between accepting a Chinese-backed regime 90 miles from Florida or pursuing military options that could destabilise the Caribbean. The fuel blockade gives Trump leverage his first-term embargo lacked, but the window for converting pressure into negotiated settlement may close before Cuba’s next harvest season begins in November.