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.
