Trump Is Laying the Groundwork to Attack Cuba. Democrats Should Push Back.

A Foolhardy Pressure Campaign

Over the past several weeks, the administration has dramatically escalated its pressure campaign on Havana. CIA Director John Ratcliffe delivered a personal warning to Cuban leaders. Classified intelligence about Cuban drone acquisitions has been leaked to the press. US Southern Command has begun drafting plans for potential military operations, surveillance flights over the island have intensified, and the Pentagon has sent a carrier strike group to the region. On May 20, the Justice Department unsealed an indictment of former President Raúl Castro, conspicuously echoing the indictment of Maduro that preceded the military operation against him. 

It is possible that all of these developments are a negotiating tactic—an attempt to frighten the Cubans into making the concessions that Trump’s oil blockade and sanctions have failed to extract. But the recent military buildup is similar to the one that presaged the operations against Iran and Venezuela. Moreover, the more that Trump, Rubio, and other members of the administration argue publicly that something must change in Cuba, the harder it becomes for them to walk away empty-handed.

As the war in Iran turns into a quagmire that experts warned about, Trump is eager for an “easy win” somewhere else. The administration views the Venezuela operation as a model for a successful military operation, and Trump may believe that a similar strike against another leftist Latin American government would play out the same way. Trump also has little patience for governments he views as having mismanaged their countries or expropriated American property—and Cuba checks both boxes. The president is also regularly exposed to pro-intervention views at Mar-a-Lago, where the Cuban-American exile community is well represented. (79% of Cubans and Cuban Americans in south Florida support a US military intervention on the island according to an April poll.) And, the issue is deeply personal to Secretary of State and National Security Advisor Marco Rubio, who appears to see catalyzing regime change in Havana as a legacy item. For all these reasons, Cuba is a potentially tempting “issue to resolve.”

However, that temptation should be resisted. Military action against Cuba would be folly. It would not achieve its objectives at acceptable cost, it would risk triggering a humanitarian and migration catastrophe, and it would further demonstrate that this administration is completely unfocused on the issues that actually matter to the American people. Democrats need to sharpen their pushback on the Trump administration’s approach—immediately.

The Administration’s Pressure Strategy Has Failed—and Force Won’t Fix It

The Trump administration’s Cuba policy has followed a steep escalation ladder in his second term. After the January military operation that ousted Venezuelan President Nicolás Maduro, the administration cut off Venezuelan oil shipments to Cuba and imposed an executive order threatening tariffs against any country that provides the island with fuel. It sanctioned GAESA, the military conglomerate that controls an estimated 40 percent of Cuba’s economy, alongside senior government and military officials, including President Díaz-Canel. And it has engaged in backchannel talks with members of the regime, hoping to identify a figure who could broker a transition from within.

None of it has worked. Cuba’s revolutionary government has an extraordinarily high pain tolerance and an extremely capable repressive apparatus. The regime survived the Special Period of the 1990s, when the collapse of the Soviet Union wiped out roughly a third of its GDP, and it has endured decades of US economic pressure since. Cuban leaders have offered marginal economic concessions—most notably, allowing diaspora Cubans to invest in businesses on the island and accepting the US offer for $100 million in aid. However, Cuban leaders maintain that the country’s economic crisis is largely a product of the longstanding US embargo, and that accepting the kind of structural changes Washington is demanding would amount to negotiating their own political extinction.

The Trump administration’s frustration is real, but the conclusion it appears to be drawing—that force can accomplish what coercion could not—is wrong. There are several options the administration appears to be weighing, and all of them would be mistakes:

• A full ground invasion cannot be ruled out, but it remains the least likely scenario given the well-known challenges of such operations. A less recognized concern that the administration likely underappreciates is that an invasion of Cuba carries unique strategic costs. The United States committed to not attack Cuba as part of the negotiations that resolved the Cuban Missile Crisis and removed Soviet nuclear weapons from the island. Violating that commitment would directly undermine America’s ability to criticize Russia for breaking its own pledge to respect Ukraine’s sovereignty after Ukraine returned Soviet-era nuclear weapons to Moscow.
• A symbolic strike on Cuban territory to ramp up pressure on the regime to surrender power would likely backfire. Cuban nationalism should not be underestimated. An attack on the island would risk rallying the population around the regime, make Cuba appear sympathetic on the world stage, and potentially make the United States look feckless if no tangible gains followed. And with US munitions stockpiles already strained by operations against Venezuela and Iran, expending more in Cuba would be strategic malpractice.
• A special forces raid modeled on the Venezuela operation faces a fundamental problem: there is no clear Cuban equivalent to Delcy Rodríguez—someone acceptable to Washington that could assume control of the country. Perhaps more importantly, there is also no Cuban Maduro, as power in Havana is more dispersed and opaque. Removing Raúl Castro, a former president who no longer holds a formal government role, would be dramatic but would ultimately change little on the ground. Attempting to remove multiple regime figures would be a far more complex and higher-risk military operation. And, even if successful, without a credible successor willing to partner with the United States, the most probable outcome is chaos—including potentially a deepening humanitarian crisis and attempts by large numbers of Cubans to flee to the United States—or further entrenchment of Cuba’s corrupt security forces.
• Continuing the maximum pressure strategy indefinitely would simply punish the Cuban people for the sins of their government. Humanitarian conditions in Cuba are in freefall. Eighty-nine percent of Cubans are currently experiencing extreme poverty. The power grid is collapsing. Schools are shut. Hospitals cannot provide lifesaving care. Cubans were the third-largest asylum-seeking nationality worldwide in 2025. Without a realistic end game, maintaining the pressure campaign will only result in mass suffering that risks triggering a migration crisis directly on America’s doorstep.

If the Trump administration wants greater economic opportunity and a growing private sector on Cuba, as it has claimed, that would have been best achieved through building on the engagement policy that Obama started in his second term. And, if instead the administration’s aim is to remove 94-year-old Raúl Castro from the scene—they could simply allow time to take its course. Absent a full invasion, the administration will almost certainly have to settle for a goal short of regime change, and such a goal would be best achieved through diplomacy. 

Democrats should say this plainly and repeatedly: a president who keeps manufacturing military crises to distract from his domestic failures is not keeping America safe. He is making it weaker, poorer, and more isolated. 

How Democrats Should Respond

Democrats should be clear-eyed, direct, and unapologetic. Cuba is a repressive regime, and no one should carry water for Havana—there is no need to praise Cuba for socioeconomic “achievements” that other countries in the Caribbean have accomplished without engaging in repression. Furthermore, Cuba’s dire economic situation is not simply a product of US policy; a major share of the damage is self-inflicted.

But opposing the Cuban government and opposing a reckless, unnecessary war are not contradictory positions. Democrats can–and should–do both. 

Cuba is a poor country with a decrepit military that poses no imminent threat to the United States. Attacking them now, especially when the Iran conflict has not been resolved, would be reckless, counterproductive, and a further demonstration that the Trump administration is unfocused on the issues that matter to the American people. And even if the most disastrous outcomes are avoided, unilateral military action aimed at “solving” all international problems is unnecessarily costly and often illegal.

The public agrees. According to polling conducted by Third Way, only 30% of Americans and 42% of Trump voters consider Cuba an enemy. Furthermore, a majority of Cuban American Democrats oppose an attack on the island. The administration is considering putting American servicemembers in harm’s way over a country that most Americans–including Trump voters–correctly do not regard as a serious threat. This is a vulnerability Democrats should exploit at every opportunity. 

The direction of Cuba policy matters for Americans, including those who are not members of the Cuban diaspora. As a country of 10 million people 90 miles away from the United States, what happens there has the potential to impact the United States directly. Should Cuba trend in a positive direction, there would be immense opportunities for mutual economic benefit and cultural exchange. However, should Trump’s policies cause Cuba to implode, the result could be mass emigration to neighboring countries, including the United States, and a security vacuum vulnerable to organized crime—all a short boat ride from Florida. 

Democrats have several lanes to work in to force the Trump administration to answer for its recklessness and to give voters a clear alternative to endless military escalation. That includes the following:  

1. Block A War: Members of Congress should proactively cosponsor the war powers resolutions in the House and Senate that would prevent President Trump from attacking Cuba without congressional authorization. This is the clearest signal that Congress will not be a rubber stamp for another manufactured war. 
2. Give Diplomacy a Runway: Congress should also consider targeted amendments to the Helms-Burton Act that would allow the United States to negotiate greater private sector investment in Cuba while reducing the legal risk facing American firms that might invest there. At present, Helms-Burton codifies the Cuba embargo in law, severely constraining the negotiating hand of the President and all but guaranteeing that, absent congressional action, most US and foreign firms will steer clear of the island. Any deal with Cuba will need to address political prisoners, property claims, corruption, and Havana’s security ties to Russia and China, among other issues, but the President should have a freer hand to elicit such concessions as part of a diplomatic process.
3. Demonstrate the Alternative: Even if this Congress fails to amend Helms-Burton, future Democratic leaders should move quickly to modernize our Cuba strategy, taking advantage of the tools the executive branch already possesses. In particular, to demonstrate that diplomatic progress is possible, the US should demand specific concessions from the Cuban regime in exchange for conditional relief from executive-branch sanctions. Ultimately, such a policy of engagement is more likely than continued pressure or confrontation to produce the changes on the island that critics of the regime have long sought, and at far less risk to US national security.

The goal should be a Cuba policy that advances American interests by promoting stability, not chaos, and avoids military action against a country where the use of force would create more problems than it solves. Democrats should own that argument and they should own it now.