The Day After in Cuba

On the beaches east of Havana, you can still see rusted remnants of watchtowers on the roofs of buildings along the island’s northern coast. Constructed in the early 1960s, after the failed Bay of Pigs invasion, these emplacements were designed to provide early warning of an attack by the United States—or “the Empire,” in Cuban revolutionary parlance. But by the time I saw them in 2002, during my time in the country as a young U.S. foreign service officer, they seemed like relics of a bygone era, monuments to Cuban leader Fidel Castro’s inability to accept the end of the Cold War and thus the island’s geopolitical irrelevance. Although its relations with the Bush administration were strained, and harsh rhetoric flew in both directions, Havana was, at best, of peripheral importance to a White House focused on expanding NATO, managing relations with China, and fighting in the Middle East. It seemed truly ludicrous to think the United States would ever bother invading Cuba.

But that was then. Today, two decades on, Washington is indeed threatening to attack Cuba’s revolutionary government. “Cuba is going to fall pretty soon,” U.S. President Donald Trump told CNN on March 6, as U.S. naval ships floated around the island. A few weeks later, the president told a business forum that after Iran, Cuba “is next.” Already, the United States has imposed a near-total oil blockade of the country, plunging much of it into darkness. Thanks to U.S. sanctions and Havana’s internal mismanagement, the country is facing economic disaster. Although the Cuban government has survived previous predictions of collapse, many observers sense that this time may actually be different. Trump, after all, has now twice made good on promises to attack U.S. adversaries. And it is obvious that the Cuban government’s model has run its course and has lost the support of many of the citizens who backed it in the past. Cubans’ desire for change is palpable.

Since the early 1960s, successive U.S. administrations have wanted to see Cuba’s communist government fall. Until Trump’s second term, however, most shied away from pursuing regime change through military force. The United States has legitimate policy interests in the island—preventing its use by geopolitical rivals, managing migration, resolving U.S. property claims. The Cuban government has been willing to discuss some of these issues, such as migration, with the United States.

But it has steadfastly rejected any discussions regarding its form of government, which the United States sees as the island’s fundamental problem. Trump’s team sees a historic opportunity to overcome the Cuban government’s resistance and bring the revolutionary period to an end. Waging war on Cuba, however, is unlikely to bring the change Trump seeks. Cuba’s regime may not be as resilient as Iran’s, but its leaders are much more entrenched than was Venezuelan President Nicolás Maduro, so an effort to unseat them would likely yield not a quick victory. What it would do is open the door to a variety of dangerous possibilities, such as a protracted, bloody insurgency or societal collapse.

Rather than trying to bring change to Cuba by force, the Trump administration should use its leverage to engage in diplomacy. It should promise to forswear military action if Havana distances itself from U.S. rivals. It should offer economic relief in exchange for pro-market reforms and political openings. It should urgently review how its sanctions regime may, paradoxically, stifle reforms it has long sought. And finally, it should push to empower Cuba’s own people, unlocking their economic and political creativity. Doing so may not immediately transform the island into a democracy, but it will directly aid the intended beneficiaries of U.S. policy—Cuban citizens—and set the stage for a sustained national recovery.

SLOUCHING TOWARD WARFARE

Since January 2025, the Trump administration has slapped escalating restrictions on Cuba in what seems like an attempt to break the island’s economy. In addition to imposing an oil blockade, the United States has expanded sanctions against Cuban government entities. It has imposed Treasury Department designations on a growing list of individual Cuban officials and their families. Most important, the Trump administration issued an executive order sanctioning foreign companies doing business with Cuba’s military-owned megafirm GAESA. That has led longtime foreign investors and economic partners, such as the Hapag Lloyd shipping firm and the Iberostar hotel chain, to abandon the island. These investors have been further deterred by American naval activity near Cuban waters and ramped up U.S. surveillance flights, which leave no doubt about the risk of an attack.

The Trump administration’s measures have changed Havana’s calculus. Cuba’s leaders appear convinced, with good cause, that these actions are a prelude to a U.S. military assault or invasion. But so far, Washington’s moves have failed to coerce the Cuban government into serious reforms. There are two simple reasons for the inaction: first, the Cuban leadership has long resisted reforms such as expanding the role of the private sector because they fear such steps will irretrievably erode their power. Second, Cuba’s leaders do not trust U.S. officials to offer relief in exchange for change. Instead, they appear to have concluded that the Trump administration is determined to remove them from power no matter what, just as it did with Maduro in Venezuela and with Supreme Leader Ali Khamenei and his associates in Iran. As a result, they see little upside to trying to mollify Washington.

Those officials, of course, might be right. Trump has favored force over diplomacy during his second term, so he could well be preparing to either kill or capture Cuban President Miguel Díaz-Canel and former president Raúl Castro (who remains an emblematic and powerful figure, despite having just turned 95). The Trump administration could then try to replace them with leaders who are happy to jettison the country’s revolutionary system in favor of cooperation with the United States.

But the Venezuela operation worked because members of Maduro’s regime, most notably Vice President Delcy Rodríguez, appeared to anticipate his ouster and were immediately ready to cooperate with U.S. demands. Such an outcome is unlikely in Havana. The Cuban government is far more entrenched and cohesive than was Maduro’s. It has been in power for 67 years. There is no indication of deep political or personal divisions between its top officials—and thus little to suggest that there is a Rodríguez waiting to take command. (U.S. Secretary of State Marco Rubio acknowledged as much in Congressional testimony on June 3.)

Even if Cuba had a “Delcy” figure, the island’s authority is too dispersed for a single person to quickly consolidate power. Even before Fidel Castro died, in 2016, Cuba’s regime already was effectively governed by a consortium of officials drawn from its various power centers. The Communist Party Politburo, the presidency, the armed forces, the Ministry of the Interior, administrators of state and state-affiliated companies, and provincial leaders all have real sway. To make a deal with the Cuban government, then, the United States would need to get buy-in from a large group of influential actors. And its recent federal indictment of Raúl Castro in connection with the 1996 downing of U.S. civilian aircraft has probably made the country’s leaders more fearful of American intentions.

Cuban officials, of course, will have a tough time resisting a U.S. military operation. The island is barely more than five percent the size of Iran geographically, and its armed services are also significantly smaller and more decrepit. Most of the country’s military would probably be wiped out in a matter of hours or days. But that does not mean the result would be easy regime change. Cuba’s military posture is built around a “War of All Peoples” doctrine that envisions losing a conventional conflict to U.S. invaders, followed by an extended insurgency against an occupying force. Arms caches are already positioned around the country, and other support structures are in place to facilitate irregular resistance that Cuban units have long trained for. Even if average Cuban citizens might not support guerrilla warfare, there is a risk that soldiers could hunker down and make life hellish for U.S. forces.

PEACE FOR PROSPERITY

Maximum pressure and military action are unlikely to change Cuba in the ways that Washington wants. But there is another option: substantive, comprehensive bilateral negotiations. The United States, in other words, should use carrots as well as sticks to change Cuba’s calculus, promising relief and security in exchange for better policies.

To do so, however, the two sides need to be able to communicate directly through consistent, high-level channels. Such an arrangement must provide the two parties with an opportunity to speak discreetly. Alongside Ben Rhodes, I spent nearly two years participating in talks that helped set the stage for President Barack Obama’s diplomatic opening to Cuba. These discussions were often difficult, and we held no illusions that we could convince our counterparts of American views on democracy and human rights. But direct communication and the ability to speak plainly regarding the views of our respective leaders over weeks and months were vital to the success of our efforts.

CIA Director John Ratcliffe’s May 14 visit to Havana could have been a good opportunity for establishing such a channel through Cuba’s powerful Ministry of the Interior. U.S. Southern Command leader Francis Donovan’s visit to the island two weeks later was similarly promising, because he engaged Cuba’s power brokers in the armed forces. Such contacts can be more effective when the same teams engage over time rather than holding one-off meetings with no follow-up. Familiarity helps, even when trust is absent.

After they have established durable channels, the two countries can turn to more substantive matters. U.S. negotiators might begin with the issues that most urgently concern the United States rather than with domestic topics that Cuba will be far more reticent to discuss. Washington, for instance, could demand that Havana remove Chinese and Russian listening posts, which allow Beijing and Moscow to eavesdrop on U.S. military communications, among other targets. In exchange, Washington might pledge not to attack Cuba’s government. Cuba could also offer to remove roadblocks to foreign investment and, especially, to the growth of the country’s private sector. In return, the United States might, for example, offer technical assistance to the Cuban banking system to help support subsequent reforms.

The Trump administration should then turn to encouraging domestic political reforms. It could promise, for example, to gradually lift trade restrictions and offer other kinds of economic relief if Cuba offers more space for regime critics, stops detaining opponents, releases all remaining political prisoners, and begins rolling back constraints on Internet use and restrictions on nonstate media. Although such steps will not by themselves democratize the country, which remains highly authoritarian, they can at least set Cuba on a more liberal course.

LAND OF OPPORTUNITY

The Trump administration will not be able to unilaterally lift every American restriction on the island—many sanctions are codified in U.S. law—and it may not fully understand the extent to which U.S. restrictions could lead to a stillborn Cuban recovery. Trump officials will thus have to persuade Congress to roll these back, or at least give the president the power to eventually do so. That will not be an easy task. Republicans and some Democrats in Congress have long supported sanctions aimed at promoting regime change in Cuba. But the Trump administration is uniquely well positioned to get the House and Senate to change course. Trump commands near-total fealty from Republicans, and he has built up a great deal of credibility among Cuban Americans. The president, for example, earned enormous plaudits from the diaspora for his tougher sanctions and the indictment of Raúl Castro. He should now encourage Cuban Americans and their backers in Congress to accept greater flexibility in the implementation of Cuban sanctions as bargaining chips in exchange for Cuban political and economic progress and to support swift changes to the U.S. embargo to prevent it from stifling reform efforts.

To persuade both Cuban Americans and congressional representatives, the White House might point to what transpired in Nicaragua in the decades after the 1990 electoral defeat of President Daniel Ortega. Ortega, a Cuban-allied revolutionary who came to power in 1979, represented the expansion of Soviet influence to Central America. He earned additional U.S. antipathy—and congressional restrictions on aid to Nicaragua—because of his expropriation of homes, businesses, and ranches from wealthy Nicaraguans and foreigners, including Americans. Although the United States waged a proxy war against Ortega’s government through its support for the contra movement, Ortega ended up losing power to Violeta Chamorro, a U.S.-aligned figure, in an unexpectedly free and fair election in 1990. Ortega’s adversaries in Congress were thrilled by his ouster, but they refused to lift aid restrictions after Chamorro won. (In fact, they expanded them.) As a result, the Nicaraguan economy continued to struggle, and in 2007 Ortega won back power. He has ruled as a dictator ever since.

The United States cannot, by itself, fix all of Cuba’s economic ills. Even before Trump amped up U.S. pressure, the island was facing severe shortages. The Cuban economy contracted by 11 percent between 2019 and 2024, according to the United Nations, and electricity generation fell by 25 percent in roughly the same period. The country has suffered from chronic inflation since it clumsily unified its dual-currency system in 2021. The island’s largest source of hard currency—tourism—never fully recovered from the COVID-19 pandemic, dropping by 62 percent between 2018 and 2025. And 1.7 million Cubans left the country between 2020 and 2024, gutting its labor force. To solve these problems, the Cuban government must dramatically expand the role of the private sector and give up the kinds of economic controls that allies such as China and Vietnam abandoned long ago. The Cuban government should, for example, eliminate restrictions on the number of employees private companies can hire, expand access to credit for private businesses, allow private ownership of farms, and permit foreign investors to hire employees directly rather than through the government.

But American sanctions have played an enormous role in the country’s devastation, and recovery is impossible while they remain in place, at least in their current form. Washington should therefore return to its messaging from earlier in 2026, when it suggested that positive steps by Cuba would open the door to de-escalation and economic relief. American officials could even make sure that whatever relief they provide helps Cuba’s reforms succeed by authorizing increased U.S. commerce with Cuba’s nascent private sector and otherwise removing barriers to Cuban citizens’ efforts to resolve their own challenges.

If Washington’s efforts succeed, the United States could unlock Cuba’s most potent resource: its people. Although international attention is understandably centered on what the Trump administration might do to the island and how its government will respond, it is ultimately Cuban citizens who will determine their country’s future. Even in the worst moments, their resilience and ingenuity have proved powerful forces. In the early 1990s, thousands of Cubans became urban farmers overnight to get through the crisis that followed the end of Soviet aid. Cuban vehicles from the 1950s may be extraordinary survivors, but perhaps more impressive are the fans, refrigerators, and other appliances dating back to the 1940s that are still running on homemade replacement parts. Even today’s depleted, exhausted Cubans have immense ingenuity and ambition; they are waiting for an opportunity to more than just survive and instead use that energy to rebuild their lives and their country.

A U.S.-Cuban war is certainly a possibility. Such a conflict would be unnecessary and more likely to yield lasting harm for both Cuba and the United States than to secure Cuban democracy and prosperity. But there is still time to lower tensions between the two countries by using American pressure as a tool of diplomacy. The citizens of both countries deserve a chance to put their tortured history behind them, leaving those rusting watchtowers along Cuba’s beaches as symbols of a conflict avoided rather than one that arrived.

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