None would guarantee a favorable outcome for the United States.
A former architect of U.S. Latin American policy has placed three military options against Cuba into public view, not as a call to action, but as a sober accounting of what action might cost. Writing in The Economist, Richard Feinberg reminds us that the distance between capability and wisdom is often where history's gravest miscalculations are made. Cuba, shaped by decades of revolutionary narrative and geographic particularity, is not a problem that yields easily to force — and the current drumbeat of economic and diplomatic pressure may itself be the strategy, not merely its prelude.
- A credentialed former NSC official has named Raúl Castro as a potential military target, raising the stakes of what had been largely rhetorical pressure on Havana.
- The Pentagon and Southern Command are reported to have contingency plans ready, waiting only for a presidential order that has not yet come.
- Trump publicly stepped back from immediate escalation on May 21st, yet the administration is simultaneously preparing for a scenario in which Cuba collapses into chaos.
- Cuba's geography, political cohesion, and capacity for internal resistance make all three military options — targeted strikes, precision airstrikes, or full invasion — deeply uncertain in outcome.
- Havana is already invoking the memory of 1961 and 1996, activating its long-standing narrative of defiance against American power as a shield and a rallying cry.
Richard Feinberg, once responsible for Latin American affairs at the National Security Council, recently outlined three military scenarios the United States might pursue against Cuba in an analysis for The Economist. The options range from a surgical strike on top leadership — with Raúl Castro named as the primary target — to precision airstrikes aimed at pressuring Havana or degrading its defenses, to a full-scale invasion. Feinberg's framing was not advocacy; it was warning. Each path, he argued, carries serious and unresolved risks.
The analysis arrives against a backdrop of escalating U.S. pressure. The Trump administration has tightened economic sanctions and filed criminal charges against Raúl Castro, a campaign some observers compare to the squeeze that preceded Nicolás Maduro's fall in Venezuela. Politico has reported that the Pentagon and Southern Command have war plans prepared and are awaiting only a presidential directive. Yet Trump himself stated on May 21st that immediate escalation was neither planned nor necessary — while Axios simultaneously reported that Washington is preparing contingency plans for a Cuban collapse, suggesting a strategy of graduated pressure rather than imminent action.
What makes Cuba distinct from Venezuela, The Economist's analysis notes, is the island's geography, its political structure, and the likelihood of organized internal resistance — factors that make military outcomes genuinely uncertain. The Cuban government, for its part, has characterized recent contacts with U.S. Southern Command as constructive, while accusing Trump of reviving the specter of 1996, when the downing of civilian aircraft brought the two countries close to open conflict. That history, like the memory of the Bay of Pigs before it, remains a living instrument of Cuban national narrative.
What the full picture reveals is an administration wielding pressure as a tool — economic, diplomatic, and military in posture — without yet committing to its sharpest edge. Feinberg's own conclusion is the most clarifying: even if the United States were to execute any of the three options he described, none would guarantee a favorable result. The gap between what a nation can do and what it can achieve may be the most consequential fact in this unfolding story.
Richard Feinberg, who once directed Latin American affairs for the National Security Council, laid out three distinct military paths the United States might pursue against Cuba in a recent analysis for The Economist. Each one, he warned, carries serious problems.
The first scenario involves a surgical strike against Cuba's top leadership—the kind of operation Washington has discussed in relation to Venezuela. The second calls for precision airstrikes meant either to pressure the Cuban government into negotiations or to degrade its air defenses. The third, the most severe, would be a full-scale invasion. When Feinberg addressed the leadership-targeting option directly, he named names: Raúl Castro would be the primary objective.
But The Economist's analysis cuts against any sense of inevitability. Cuba is not Venezuela. The island's geography, its political structure, and the likelihood of internal resistance all mean that any military operation would face uncertain outcomes and considerable risk. This distinction matters. It suggests that even if Washington has the capability to act, capability does not equal wisdom or likelihood of success.
The timing of this discussion is not abstract. The Trump administration has been steadily tightening pressure on Havana through economic sanctions and criminal charges filed against Raúl Castro—a campaign that observers have compared to the escalation that preceded Nicolás Maduro's fall in Venezuela. According to reporting from Politico, the Pentagon and Southern Command have war plans prepared and, as one account put it, are simply awaiting the order. Both the Pentagon and the regional military command have conducted planning sessions for various Cuba scenarios, though no confirmed presidential directive has been issued.
Trump himself seemed to pump the brakes on May 21st, stating flatly that there would be no immediate escalation and that he did not believe it was necessary. Yet Axios reported that the United States is simultaneously preparing contingency plans for what happens if Cuba descends into chaos—suggesting a strategy of graduated pressure rather than immediate intervention. The Cuban government, meanwhile, characterized a recent meeting with the U.S. Southern Command as positive, while accusing Trump of reviving the memory of 1996, when the downing of civilian aircraft nearly triggered a larger crisis.
Historically, Cuba has wielded the threat of American military action as a tool of national narrative—a story of defiance and resilience that has endured since the failed Bay of Pigs invasion in 1961. That invasion, organized by the CIA with Cuban exiles, became a founding myth of the revolution. Now, as Trump convened his security cabinet on May 12th to evaluate pressure options, that old narrative is being activated again.
What emerges from all this is a picture of Washington pursuing graduated pressure—economic, diplomatic, and military posturing—rather than rushing toward direct intervention. Yet even Feinberg's own analysis, as presented in The Economist, reaches a sobering conclusion: if any of the three military options he outlined were actually executed, none would guarantee a favorable outcome for the United States. That gap between capability and certainty may be the most important fact of all.
Citas Notables
Raúl Castro would be the primary objective in a leadership-targeting operation.— Richard Feinberg, former NSC director for Latin America
No escalation. I don't think it's necessary.— Trump, May 21st
La Conversación del Hearth Otra perspectiva de la historia
Why would Feinberg, someone who worked inside the security apparatus, be laying out these military options so publicly?
He's not advocating for them. He's warning against them. By naming the problems with each scenario, he's essentially making the case that none of them work—which is a way of influencing policy from outside the government.
But doesn't publishing this in The Economist just give people ideas?
Perhaps. But the Pentagon and Southern Command already have these plans. What Feinberg is doing is forcing the public conversation to reckon with the actual costs and risks, not the fantasy version where a quick strike solves the problem.
Why is Cuba different from Venezuela in this regard?
Geography, mainly. Venezuela is on the mainland. Cuba is an island with no easy exit for the regime and no easy occupation for an invader. The political structure is also more consolidated—there's no equivalent to the fractures that opened up in Venezuela's military and government.
So Trump saying "no escalation" on May 21st—does that settle it?
Not really. He said he doesn't think it's necessary right now. But the administration is still preparing for chaos scenarios and maintaining pressure. It's a both-and situation: not invading today, but keeping the option alive and the pressure on.
What does Cuba get out of that meeting with Southern Command?
Legitimacy, mainly. It shows their government can negotiate with the Americans as equals, not as a target. It also gives them a chance to signal that they're not the ones escalating—that any conflict would be Washington's choice.