Monroe Doctrine Reborn: Trump Targets Cuba in Bold Regime Push

Paul Riverbank, 1/24/2026The Trump administration intensifies pressure on Cuba, invoking the Monroe Doctrine and hinting at more aggressive tactics—raising stakes for Havana and signaling a bold, risky new era in U.S. policy for the hemisphere.

In Washington, this crisis hasn’t gone unnoticed. Some inside the Trump administration are viewing Cuba’s troubles as an opportunity, perhaps even a pivotal one. Senior officials, emboldened by their recent actions in Venezuela, are talking openly about using the same strategy—now described by some insiders as their “blueprint”—for Havana as well.

It’s not just talk. After Maduro’s ouster, stories surfaced about an unnamed source from inside his own camp, passing key information to U.S. intelligence. Sources told the Wall Street Journal it was this insider help that tipped the balance. The lesson for Washington: If the right people can be persuaded—or pressured—change might come faster than expected. Now, U.S. officials are reportedly reaching out to Cuban dissidents and even some figures quietly serving inside the Cuban government. There’s a sense—hard to miss, if you spend time among Miami’s exile community—that cracks are appearing in the old guard.

Reading through the administration’s National Security Strategy, the intent is about as subtle as a midnight freight train. Gone, supposedly, are the days of “benign neglect.” In their place: vows to enforce the Monroe Doctrine, restore America’s dominance in the Western Hemisphere, and reshape the regional chessboard with unmistakable U.S. fingerprints.

President Trump, characteristically blunt, posted recently, “THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA — ZERO! I strongly suggest they make a deal, BEFORE IT IS TOO LATE.” Those words aren’t just bluster. Administration officials have floated the possibility of a naval blockade—an extreme step, once rarely discussed in serious policy circles, but now apparently on the table as one of several options. Politico cited sources who say the White House is giving these measures real consideration, not just rehearsing old Cold War scripts.

Senator Marco Rubio, whose family’s own roots run deep in Cuba, has emerged as a leading public face. “Cuba is a failing nation, a very badly failing nation, and we want to help the people,” he said this month. His warning rattled around Havana: “If I lived in Havana, and I was in the government, I’d be concerned.” For the inner circle in Cuba, the message is hard to ignore, though it’s unclear exactly how many are listening—or weighing their options.

Meanwhile, the Pentagon isn’t just focused on the Caribbean. The USS Abraham Lincoln carrier group is steaming toward the Persian Gulf, a reminder that U.S. force projection isn’t limited to Latin America. “We have a big force going toward Iran. I’d rather not see anything happen, but we’re watching them very closely,” Trump announced, signaling that American resolve is being flexed well beyond its immediate neighborhood.

There’s an unmistakable sense of hurry behind these moves. U.S. officials keep insisting there isn’t a fixed deadline for action, but privately, they acknowledge that the current window—the confluence of regional turmoil and Cuba’s deepening economic pain—might not stay open forever. For regime insiders looking for an exit strategy, there’s a sharp implication: hesitation could have consequences.

Of course, all of this is easy for U.S. policymakers to say from the safety of Washington and Miami. Cuba’s leadership has weathered embargoes, attempted invasions, covert action, and isolated hardship before. Havana’s streets are filled with rumor and speculation, but no one can say for sure whether this pressure will bring change or simply new waves of hardship.

Supporters of the administration frame the strategy as long-overdue, a bold application of American will for a democratic region. Critics warn of the risks: overreach, backlash, and the possibility that squeezing Cuba in such dramatic fashion could ignite unintended consequences, destabilizing not just an island but the whole region.

For now, all sides are watching, waiting, and—at least for Cuba’s ordinary citizens—hoping that whatever comes next brings light, rather than further darkness, to a nation already weary from waiting.

A chilly late afternoon in Havana, streetlights flicker uncertainly along the Malecón. For weeks, much of the island has been wrestling with power outages—long, grinding hours with neither fans nor refrigeration—while gas station lines curl around the block. Oil, once trickling in from Venezuela, now seems little more than a rumor.In Washington, this crisis hasn’t gone unnoticed. Some inside the Trump administration are viewing Cuba’s troubles as an opportunity, perhaps even a pivotal one. Senior officials, emboldened by their recent actions in Venezuela, are talking openly about using the same strategy—now described by some insiders as their “blueprint”—for Havana as well.It’s not just talk. After Maduro’s ouster, stories surfaced about an unnamed source from inside his own camp, passing key information to U.S. intelligence. Sources told the Wall Street Journal it was this insider help that tipped the balance. The lesson for Washington: If the right people can be persuaded—or pressured—change might come faster than expected. Now, U.S. officials are reportedly reaching out to Cuban dissidents and even some figures quietly serving inside the Cuban government. There’s a sense—hard to miss, if you spend time among Miami’s exile community—that cracks are appearing in the old guard.Reading through the administration’s National Security Strategy, the intent is about as subtle as a midnight freight train. Gone, supposedly, are the days of “benign neglect.” In their place: vows to enforce the Monroe Doctrine, restore America’s dominance in the Western Hemisphere, and reshape the regional chessboard with unmistakable U.S. fingerprints.President Trump, characteristically blunt, posted recently, “THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA — ZERO! I strongly suggest they make a deal, BEFORE IT IS TOO LATE.” Those words aren’t just bluster. Administration officials have floated the possibility of a naval blockade—an extreme step, once rarely discussed in serious policy circles, but now apparently on the table as one of several options. Politico cited sources who say the White House is giving these measures real consideration, not just rehearsing old Cold War scripts.Senator Marco Rubio, whose family’s own roots run deep in Cuba, has emerged as a leading public face. “Cuba is a failing nation, a very badly failing nation, and we want to help the people,” he said this month. His warning rattled around Havana: “If I lived in Havana, and I was in the government, I’d be concerned.” For the inner circle in Cuba, the message is hard to ignore, though it’s unclear exactly how many are listening—or weighing their options.Meanwhile, the Pentagon isn’t just focused on the Caribbean. The USS Abraham Lincoln carrier group is steaming toward the Persian Gulf, a reminder that U.S. force projection isn’t limited to Latin America. “We have a big force going toward Iran. I’d rather not see anything happen, but we’re watching them very closely,” Trump announced, signaling that American resolve is being flexed well beyond its immediate neighborhood.There’s an unmistakable sense of hurry behind these moves. U.S. officials keep insisting there isn’t a fixed deadline for action, but privately, they acknowledge that the current window—the confluence of regional turmoil and Cuba’s deepening economic pain—might not stay open forever. For regime insiders looking for an exit strategy, there’s a sharp implication: hesitation could have consequences.Of course, all of this is easy for U.S. policymakers to say from the safety of Washington and Miami. Cuba’s leadership has weathered embargoes, attempted invasions, covert action, and isolated hardship before. Havana’s streets are filled with rumor and speculation, but no one can say for sure whether this pressure will bring change or simply new waves of hardship.Supporters of the administration frame the strategy as long-overdue, a bold application of American will for a democratic region. Critics warn of the risks: overreach, backlash, and the possibility that squeezing Cuba in such dramatic fashion could ignite unintended consequences, destabilizing not just an island but the whole region.For now, all sides are watching, waiting, and—at least for Cuba’s ordinary citizens—hoping that whatever comes next brings light, rather than further darkness, to a nation already weary from waiting.