Sanctions Over Speed: How the White House Quietly Recalibrated Its Cuba Bet

Nothing about Cuba’s predicament looked survivable back in January. Within hours of U.S. forces seizing Venezuelan leader Nicolás Maduro in a January 3 raid on Caracas, President Trump began treating Havana’s collapse as a foregone conclusion. Cuba had leaned on Venezuelan oil and cash for years, and with Maduro gone, that lifeline was cut. Trump posted on Truth Social that Havana should strike a deal “before it is too late,” warning there would be no more Venezuelan money or fuel reaching the island. Seven months later, none of that has translated into the regime change he all but promised. Cuba’s Communist leadership is intact, U.S.-Cuban talks have hit a wall, and the momentum that once seemed unstoppable has visibly cooled.

The pressure escalated fast at first. Administration officials reportedly went looking for Cuban insiders willing to help engineer a leadership change. By late February, with the island’s fuel-starved economy buckling, Trump told reporters Havana had run out of money entirely, then mused, without elaborating, that “we could very well end up having a friendly takeover of Cuba.” Roughly a week after that, he indicated Cuba would have to wait its turn until Secretary of State Marco Rubio wrapped up the Iran conflict — a timeline measured in months rather than the days his earlier rhetoric implied.

Rubio recasts the clock

Rubio has since done more than anyone in the administration to manage down expectations. Pressed on whether Cuba was “next,” he said only that he’s confident the island will be on an “irreversible path” toward a different future by the time this administration’s term ends — a horizon of years, not weeks. He’s compared dismantling a 70-year system to trying to yank out something that has grown too many roots to remove overnight, pointing to Eastern Europe’s multi-year transitions away from communism as his model.

That same instinct for caution surfaces in how Rubio describes his own family. He has long called his Cuban-born parents exiles who fled after Castro’s takeover, a narrative that has anchored his political identity for years. Immigration paperwork tells a more layered story: his parents arrived in the U.S. in 1956, nearly three years before the revolution, not fleeing it in the moment. Rubio has attributed the mismatch to family memory rather than exaggeration, saying the dates came from what his parents told him decades after the fact.

The back channel and its limits

Rubio’s main line into Havana runs through Raúl Castro’s grandson, Raúl Guillermo Rodríguez Castro, a 41-year-old colonel nicknamed “El Cangrejo.” He built his standing partly by heading his grandfather’s personal security detail for years before stepping into a broader political role — and partly because his late father, Gen. Luis Alberto Rodríguez López-Calleja, spent years running GAESA, the military’s business empire, before dying in 2022. The grandson has since taken over managing the family’s stake in that empire, which a Miami Herald investigation of leaked internal records found holding roughly $18 billion in reserves even as ordinary Cubans went without power for hours at a stretch. Despite that access, U.S. officials who’ve dealt with him reportedly concluded his actual authority to broker a deal is limited.

That walk-back has landed hard in Miami. University of Miami historian Michael Bustamante attributes much of the letdown to Trump’s own off-the-cuff comments, which he says South Florida activists and lawmakers inflated into commitments the White House never actually made. On the island, an online survey by the independent outlet El Toque found close to 60% of roughly 25,000 respondents favored U.S. military action to remove the government — a mood Council on Foreign Relations fellow William Freeman said he encountered widely on a recent trip, though he wondered aloud whether that support would hold once Cubans notice Washington’s attention drifting elsewhere. Meanwhile, Miami-based influencer Alexander Otaola is organizing an October rally in Washington under the hashtag #DoItTrumpDoIt to push the administration toward faster action.

Iran, an earthquake, and an election calendar

Analysts point to competing crises for the slowdown. Florida International University’s Brian Fonseca said the drawn-out war with Iran and an earthquake that struck Venezuela pulled attention and resources away right as momentum was building — and the mass uprising many had expected in Cuba simply didn’t happen. With midterm elections approaching and voters focused on the economy, Cuba Study Group executive president Ric Herrero doubts Republicans will spend political capital on Cuba now, describing a window that opened and shut while Rubio weighs a possible presidential run of his own.

A strategy built on outlasting, not overthrowing

Some observers doubt a fast takeover was ever really the plan. John Kavulich, who heads the U.S.-Cuba Trade and Economic Council, argues the administration is instead grinding Havana down through sanctions and its fuel squeeze — a campaign that has already pushed the Spanish hotel chains Meliá and Iberostar, along with the Canadian mining company Sherritt, to suspend their Cuban operations entirely. Rubio has leaned into that framing, arguing the island’s leadership needs a wholesale overhaul and telling Axios that every workaround Havana finds gets shut down in turn. The risk is real: prolonged blackouts and shortages could deepen an already severe humanitarian crisis and push more Cubans to migrate, with no guarantee that a government long practiced at outlasting hardship will actually crack.

Waiting for the image that changes everything

Daily life on the island keeps getting harder in the meantime — families sleeping outside through blackouts, residents hauling water from broken pipes, a bottle of cooking oil costing roughly twice an average month’s pay. Kavulich doesn’t think diplomacy will decide how this ends. He predicts the real trigger will be a photograph — he described it as an image of “an old woman lying dead on a pile of garbage” on a Havana street, stark enough to force either government to act. For now, neither side is blinking.