The Logic of Pressing for Change in Cuba Now

The Trump administration’s National Security Strategy, released in December 2025, heralded a return of the United States to the Western Hemisphere. Not only is the region foundational to U.S. global power and power projection capability, but the Trump administration has cohered around three fundamental ideas in its foreign policy elevation of the Western Hemisphere. First, the United States’ absence from the region accrued to only one country’s gain: China. Second, the United States’ absence did not represent a “benign neglect” of the Western Hemisphere but, in fact, generated economic and security concerns. And third, those economic and security concerns, ignored by previous administrations, have grown in such magnitude that the United States, strategically, can no longer afford to ignore them. Thus, the Trump administration’s focus on the Western Hemisphere, and on Venezuela in 2025, and now on Cuba in 2026. 

Both countries are authoritarian regimes that have been permitted to fester for decades, propelling unsustainable migration, spinning networks of transnational organized crime, illicitly financing regional political campaigns, and destabilizing the entire Western Hemisphere. Perhaps most importantly for U.S. strategy, both regimes have served as principal beachheads for great power adversaries to project power near U.S. shores. In Venezuela’s case, close ties with Russia, China, and Iran have seen Venezuela play host to Russian Navy port calls, Iranian proxy groups, and Chinese intelligence operations. In Cuba’s case, Chinese and Russian signals intelligence facilities seek to leverage the country’s geography and strategic location to extend espionage outposts covering the U.S. East Coast, which features some of the most important military installations maintained by the United States. Reports in 2023 even indicated that China and Cuba had signed an agreement to establish a training base in the country. 

Whereas past administrations sought to deal with Venezuela through dead-end negotiations and selective sanctions relief, in the early morning hours of January 3rd, the Trump administration launched Operation Absolute Resolve, a daring special forces raid of Venezuelan dictator Nicolás Maduro’s compound to capture him and his wife and whisk them to New York City, to eventually stand trial on charges stemming from a 2020 indictment for drug trafficking. The highly successful mission has reset U.S. relations with Venezuela, particularly under the country’s de facto Vice President Delcy Rodriguez, who now exercises power as “interim authority” (to use the term preferred by the U.S. government). For the United States, this has created an opportunity for an economic, diplomatic, and, eventually, political opening. The most immediate losers of Operation Absolute Resolve? China, Russia, and Iran. 

It was also a blow to Cuba, Venezuela’s longtime ally and eventual colonizer. Over the 2000s and 2010s, Havana extended its influence over Caracas and ensured access to its vast oil reserves. Eventually, Venezuela and Cuba settled into a comfortable and crude tradeoff: Venezuelan oil in exchange for Cuban repression tactics, especially counterintelligence on Venezuela’s armed forces, meant to prevent coup attempts. Thirty two Cubans died defending Maduro in Operation Absolute Resolve. Now that the United States exercises significant influence over Venezuela’s economic decisions, it immediately cut Havana’s oil lifeline. The Trump administration threatened secondary tariffs on countries that tried to deliver oil to Havana. As a result, one of the country’s last major shipments occurred in early January. Other erstwhile fuel providers, such as Mexico, have stopped sending oil to Cuba. (Recent reports suggest that a tanker with Russian oil has been permitted to dock in Cuba.) 

The result has been a Cuban economy, already on the precipice of collapse, finally shorn of its Venezuelan lifeline. Cuba’s moribund economy has outlasted exhaustion thanks in part to Venezuela’s oil shipments, which deferred a hastier reckoning with the Cuban Communist Party’s economic incompetence. More than one million Cubans have left the island in the last few years — about 10 percent of the country’s population — due to the economic chaos and brutal repression. 

Under threat of further pressure, the Trump administration has taken advantage of the moment to initiate talks with members of Cuba’s Castro family regarding economic and political openings. Public details have been scant, but Secretary of State Marco Rubio has emphasized the need to build an economy that functions for average Cubans. The island experiences routine and rolling blackouts, and the state has reduced daily rations of bread and milk. Since the presidency of Raúl Castro, the military’s state-backed firm has taken over the most lucrative industries, such as tourism, and sits on billions in bank accounts. 

But without genuine political reform, however, options are limited to superficial changes. The Cuban Communist Party has announced an openness to investment from the Cuban diaspora. Predictably, the announcement has been met with deep skepticism. As Wall Street Journal columnist Mary Anastasia O’Grady puts it: “those who were forced to flee and whose property was stolen are invited to buy it back from the thieves. It’s the latest Cuban con job.” Cuba remains a one-party state subject to severe political and economic restrictions. This is to say nothing of the legal restrictions on U.S. investment in Cuba from a mechanics perspective. After all, the U.S. embargo on Cuba is a bipartisan law, having passed in 1996 with overwhelming majorities in the U.S. House and Senate; the Helms-Burton Act imposes stricter rules on trade with Cuba than a normal sanctions regime, which can be altered with licenses from the United States Treasury Department. The Helms-Burton Act’s restrictions can be loosened only after the United States certifies political changes—a “transition government,” in the words of the legislation—on the island. 

As expected, Cuba has denied that political changes are a matter open to negotiation with the United States. Yet the Cuban Communist Party senses the current moment as critical to its survival, given that the country is on the verge of collapse and relief from U.S. pressure is nowhere on the horizon. The question then becomes how to effect political change that satisfies the United States while appearing organic rather than dictated by Washington. 

For the United States, this may just be a matter of time. Indeed, President Trump has repeated on numerous occasions that he believes Cuba is on the verge of failure. The key will be to effect change while avoiding Cuba's entering a humanitarian collapse or inducing further destabilizing migration flows. The president has also hinted at his willingness to reprise the use of force if necessary. As the Cuban regime scrambles to respond, play for time, and position itself in negotiations, the United States is scanning the political class for a less ideological, more pragmatic leader. The Trump administration’s strategy in Venezuela reveals lessons learned from the disasters in Iraq and Afghanistan—overnight regime change rarely meets with success. Instead, Venezuela points to the possibility that regime management and eventual phased transition are the preferred strategy over outright collapse, providing a chance at the former without the chaos of the latter. 

The Trump administration has already accelerated geopolitical competition in the Western Hemisphere. The National Security Strategy introduces a “Trump Corollary to the Monroe Doctrine,” reviving the United States’ oldest foreign policy doctrine and restoring the idea of strategic denial. Early efforts to weaken China’s position at the Panama Canal sought to trim important sources of Beijing’s influence, while the capture of Maduro has pushed Western Hemisphere geopolitics into overdrive. If the Trump administration manages to steer Cuba toward transition, too, that could herald the largest leap forward for the U.S. geopolitical position in the Western Hemisphere since the end of the Cold War, when the region largely democratized. Slowly, but steadily, the Trump administration appears to be crimping important sources of Chinese and Russian influence in the Americas, returning the United States to strategic solvency in the region as the country girds for a longer term competition with China. What happens in Cuba would lend crucial support to this goal. 

Ryan C. Berg is the Director of the Americas Program at the Center for Strategic and International Studies (CSIS) and the head of the Future of Venezuela Initiative at CSIS.