George Friedman believes the Trump administration's strategy regarding Cuba centers on the economic strangulation of the island to trigger an internal mutiny. Speaking on a Geopolitical Futures podcast, the analyst stated that following the capture of Venezuelan President Nicolas Maduro by US special forces on January 3, 2026, oil shipments to Cuba have effectively ceased—marking one of the operation's key objectives.
"By cutting off supplies from Venezuela, the United States aimed, in part, specifically to sever Cuba's access to oil," Friedman stated. He assessed the island's economy as being "in ruins—and it has been in that state for a long time." The Cuban administration has failed: "This island could prosper. But it does not."
Friedman noted that US concerns regarding Cuba date back to the 19th century, when Washington feared Spain could utilize the island to project power onto the American coast. "John Kennedy, who was certainly no Donald Trump, maintained extremely tense relations with Cuba," the analyst observed, referencing the failed Bay of Pigs invasion in 1961.
According to Friedman, the population's threshold for suffering "was crossed many years ago," and the regime is held together solely by "ruthless internal security forces." The people find themselves trapped: emigration is difficult as authorities rarely permit it, and the US currently has no interest in an influx of Cuban refugees.
"Trump's plan is to back Cuba into a hopeless corner so the regime collapses, allowing for the subsequent use and development of Cuba—as was done for centuries before Castro," the analyst argues. However, he deems a full-scale invasion unlikely: "Cuba is big. We forget how big it is. It stretches from New York to Chicago. Occupying this territory is an extremely difficult military task." According to Friedman, Trump prefers minimal exposure: "Even with Maduro, it was a special operation: go in, grab him, and get out."
While theoretically capable of assisting Cuba, Russia is practically useless in the current context. "The Russian economy is in no condition to bolster the Cuban economy. And it is highly unlikely that Russia would commit to military action for the sake of Cuba," Friedman concluded. The most probable scenario remains a blockade and a waiting game for an internal explosion.