Emboldened by the U.S.-led ouster of Venezuelan President Nicolás Maduro, the Trump administration is now turning its focus toward Cuba, quietly searching for insiders within the Communist government who might be willing to cut a deal and help end the regime by the end of the year, according to people familiar with the effort.
Administration officials believe Cuba’s economy is nearing collapse and that the regime has never been more vulnerable, especially after losing Maduro as a key benefactor. For years, subsidized Venezuelan oil propped up Havana’s failing system, but that lifeline is now under threat. Senior U.S. officials say Maduro’s capture, and the concessions extracted from his remaining allies, are being viewed as both a blueprint and a warning for Cuba’s rulers.
President Trump made his position unmistakably clear in a Jan. 11 social media post, urging Cuba’s leaders to make a deal “before it is too late” and declaring that “NO MORE OIL OR MONEY” would be flowing to the island.
Behind the scenes, administration officials have met with Cuban exiles and civic groups in Miami and Washington, focusing on identifying someone within the current government who recognizes the regime’s weakness and may be willing to negotiate. One U.S. official said the goal is to find an insider who sees the writing on the wall and wants an exit strategy.
The Jan. 3 raid that led to Maduro’s capture was made possible by an asset within his inner circle, officials have said. That operation, carried out in Caracas, also resulted in the deaths of 32 Cuban soldiers and intelligence operatives who were embedded in Maduro’s security detail, underscoring how deeply Havana was invested in keeping him in power.
While the administration has not publicly threatened military action against Cuba, officials privately say the bold operation in Venezuela is meant to serve as an implicit warning to Havana.
U.S. intelligence assessments paint a bleak picture of Cuba’s economy, marked by severe shortages of food and medicine and rolling blackouts. Economists warn that if Venezuelan oil is fully cut off, Cuba could run out of fuel within weeks, grinding daily life to a halt.
The administration is also targeting Cuba’s overseas medical missions, one of its primary sources of hard currency, through visa bans aimed at Cuban and foreign officials accused of facilitating the program.
Trump and his inner circle, many with deep ties to Florida, view the collapse of Cuba’s Communist regime as a defining test of his national security strategy in the Western Hemisphere. Officials say Trump considers the Venezuela operation a success and points to the cooperation of acting Venezuelan President Delcy Rodríguez as proof the United States can dictate terms. A White House official described Cuba’s leaders as incompetent Marxists who have destroyed their country and said the loss of Maduro is a major setback they cannot ignore.
The State Department said it is in America’s national security interest for Cuba to be governed democratically and to stop hosting adversarial military and intelligence services.
Some Trump officials say the president is not interested in the failed regime-change strategies of the past. Instead, he favors escalating pressure while leaving open a path for negotiation, similar to the approach used in Venezuela.
Cuba’s Communist government has survived decades of U.S. pressure, from the Bay of Pigs invasion to a long-standing embargo. Unlike Venezuela, Cuba has no real political opposition or functioning civil society, making the path forward less clear.
In Miami, Maduro’s ouster has fueled optimism that Cuba could be next. Trump allies and lawmakers have shared visions of a post-Communist Cuba, while the regime in Havana insists it will not surrender. As shortages worsen and quiet protests echo through darkened streets, the administration appears determined to test whether this moment of weakness can finally bring an end to nearly seven decades of Communist rule.
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