Is Trump about to do a Venezuela on Cuba?

CUBA

Raul Castro’s indictment and reported CIA contacts with his grandson have fuelled speculation Washington may be pursuing a Venezuela-style transition strategy in Cuba – though other paths remain possible.

FROM the Bay of Pigs and the Cuban Missile Crisis to the present day, few countries have occupied such an outsized place in the American strategic imagination as Cuba.

For more than sixty years, the island has remained a geopolitical irritant, an ideological obsession and an unresolved historical wound for Washington.

Now, as the island faces rolling blackouts, severe fuel shortages and growing public unrest, some analysts believe Washington may finally sense an opening.

The indictment of Raul Castro has given fresh weight to that idea.

Last week, Washington unsealed charges against the 94-year-old revolutionary figure over the 1996 downing of two civilian aircraft operated by the exile group Brothers to the Rescue.

“This really is the big one,” Sibylline lead Americas analyst Lewis Galvin says of the indictment.

“Essentially it gives legal cover for the US to do what they did with Nicolás Maduro.”

Those suspicions deepened after reports emerged that CIA Director John Ratcliffe had travelled to Havana for discussions believed to have included Raul Guillermo Rodríguez Castro, known informally as “Raulito”, the grandson of Raul Castro and a rising figure within Cuba’s security establishment.

Before Washington’s operation against Nicolás Maduro earlier this year, US officials quietly cultivated contacts with regime insiders while tightening sanctions and publicly questioning the Venezuelan government’s legitimacy.

Delcy Rodríguez ultimately emerged as a continuity figure acceptable to parts of both the regime and Washington.

Sibylline’s latest Special Report states that Washington is “more likely to continue negotiating with influential Cuban policy-makers who share the regime’s ideological alignment but whom the Trump administration considers to be more progressive, such as security official Raúl Guillermo Rodríguez Castro”.

The report also notes there is “a realistic possibility” Cuba’s current president Miguel Díaz-Canel could eventually be removed peacefully as part of a negotiated process, though without wider regime collapse.

Behind the manoeuvring lies a country in profound crisis.

Russia, once Cuba’s principal geopolitical backer, is now heavily consumed by the war in Ukraine, while Venezuela is no longer capable of propping up Havana economically.

Against that backdrop, the Trump administration has dramatically increased pressure on Havana since January, choking off oil flows from Venezuela and Mexico, Cuba’s two main suppliers.

The shortages have crippled transport, grounded flights and pushed the electricity grid towards collapse.

“They’re getting rolling blackouts now of about 22 hours a day,” he says.

“Hospitals are shutting and they’re only doing emergency care at the moment.”

The US has also pushed regional governments to suspend Cuba’s doctor exchange programmes, cutting off a major source of foreign currency. Additional sanctions have targeted GAESA and senior Communist Party figures.

The crisis has triggered Cuba’s highest unrest levels since 2020, with demonstrations breaking out in Havana and other cities.

Meanwhile, reports emerged on 17 May that the Pentagon was assessing whether Cuba’s growing drone stockpile posed a security threat to southern Florida and Puerto Rico.

“I think these reports are being leaked on purpose as part of the pressure campaign,” he says.

For decades, Cuba has remained a defining issue within Florida politics and among the Cuban-American diaspora – a reality taking on renewed importance as Republicans look towards next year’s midterms.

Secretary of State Marco Rubio, whose family fled Cuba, is increasingly seen as the driving force behind Washington’s more assertive Western Hemisphere strategy.

“I think Rubio, who has been conspicuously absent from the Iran theatre, is the architect of Western Hemisphere policy,” adds Galvin.

“He was successful in Venezuela, which I think has probably given him more autonomy on dealing with Cuba.”

Cuban-American voters remain one of the most influential blocs in Florida, a crucial presidential battleground.

With Republicans already looking towards the midterms, any perception that the White House had forced concessions from Havana would play strongly among parts of the Cuban-American electorate.

“The prospect of leaving office with Chavismo gone in Venezuela and communism gone from Cuba,” he says, “is a big attraction for someone like Trump.”

Yet for all the increasingly heated rhetoric, the reality may prove more complicated than the comparisons suggest.

Sibylline still assesses a large-scale US military intervention as unlikely, even after doubling the probability of its “most dangerous” scenario from five to ten per cent.

Public appetite for another major US intervention also appears limited, reinforcing the White House’s preference for pressure, negotiation and elite manoeuvring over any large-scale military option.

Its most likely forecast is not invasion or regime collapse, but a negotiated economic opening in which Cuba grants concessions to US investors in exchange for fuel support and sanctions relief while the Communist Party retains power.

In that sense, the emerging strategy bears some resemblance to Washington’s approach in Venezuela.

Cuba, however, presents a very different challenge for the White House.

Unlike Venezuela, Cuba sits just 90 miles from the US mainland. Any serious humanitarian collapse would rapidly become an American political and security problem, potentially triggering large migration flows towards Florida and Puerto Rico.

Cuban-American voters may support a harder line against Havana, but widespread hunger, blackouts and humanitarian collapse could quickly become politically toxic for the White House – particularly if the pressure campaign is seen as inflicting excessive suffering on ordinary Cubans while risking a new migration crisis on America’s doorstep.

“The diaspora won’t like that,” warns Galvin. “Because it’s their people who are suffering.”

“There’s a fine line here. A humanitarian crisis that gets out of hand, or mass migration, quickly becomes a US problem.”

There are also signs that parts of the Cuban establishment may already recognise the current trajectory is unsustainable.

Raul Castro is 94 and widely believed to be in poor health.

And unlike Fidel and Raul, much of Cuba’s younger leadership never lived through the revolution itself and may place greater emphasis on economic survival than ideological purity.

“The Cubans would probably welcome some US investment,” he says.

“So there is that prospect for a breakthrough without the military option.”

For now, Washington appears determined to keep all options open while testing whether Havana is willing to bend.

But the real danger point may come later, once the White House no longer has to divide its attention with Iran.

“One there’s a final conclusion to Iran,” he says, “they can turn all their attention on Cuba.”

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