Ever since U.S. commandos removed Venezuelan President Nicolás Maduro from power in January, Washington has piled unprecedented pressure on Cuba, Caracas’s beleaguered former ally. The island’s economy had already been spiraling as a result of the first Trump administration’s “maximum pressure” sanctions, the COVID-19 pandemic, and Havana’s failure to adopt deeper economic reforms. But Cuba’s loss of access to heavily discounted Venezuelan oil dealt a lethal blow. U.S. President Donald Trump’s de facto oil blockade of the island the last five months—the White House has let through just one Russian tanker—has pushed the country to the precipice: power blackouts are now daily and unpredictable, basic services have ground to a halt, and citizens are growing desperate.
Still, in not-so-quiet contacts with Cuban emissaries over the spring, including with a grandson of former President Raúl Castro, the White House has attempted to persuade the island’s one-party state to agree to an economic and security opening rather than root-and-branch political change. Havana has not taken Washington up on the offer but has instead mostly projected confidence and tried to buy time—especially since the launch of U.S. hostilities in Iran, which it hoped would absorb the administration’s attention and sap its will for escalation closer to home.
That time is running short. Frustrated by Havana’s intransigence, the Trump administration has threatened to impose crippling new secondary sanctions on foreign companies doing business in key sectors of the Cuban economy. In a surprise mid-May visit to Havana, the director of the Central Intelligence Agency, John Ratcliffe, delivered an ultimatum to Cuba’s leadership, demanding that it break security ties with China and Russia. The United States is also laying the groundwork for a potential “law enforcement” extraction operation that might echo the capture of Maduro by indicting Castro in a U.S. court.
This is not just a story about Washington’s choices, however. For decades, the island’s government has prioritized internal control and external patrons over political and economic transformation. It has long framed negotiating with Washington under pressure as incompatible with sovereignty—and one cannot deny that the current scale of U.S. economic coercion against Cuba is morally shocking. But given the current U.S. administration’s unpredictability, the onus to avert catastrophe is now on Havana. The longer Cuban leaders treat the path forward as a matter of revolutionary dignity rather than national survival, the more certain it becomes that whatever follows will be worse.
The best path forward is a negotiated deal in which Havana makes concessions substantial enough for Trump to sell as a victory, and in so doing staves off a humanitarian collapse and puts Cuba on the road to recovery. Anything short of that raises the risk of deepening social unrest and U.S. military intervention to stabilize a cratering economy just 90 miles from Florida, an outcome both governments would prefer to avoid.
PAST THE BOILING POINT
From the moment news of Maduro’s capture broke, the Trump administration telegraphed two contrasting messages about the implications for Cuba. On the one hand, some U.S. officials told The Wall Street Journal that they were actively seeking regime change in Havana by the end of 2026. Yet diplomats also spoke to Cuban exiles in Miami and Spain about finding a “Cuban Delcy,” referring to the Venezuelan vice president under Maduro, Delcy Rodríguez, who was installed as interim leader after his removal. Cuba doesn’t have to “change all at once,” U.S. Secretary of State Marco Rubio remarked in February.
Cuba offered a few gestures in response: it released a handful of political detainees, issued a broader pardon decree covering 2,000 common prisoners, and committed to allowing Cuban Americans to invest in the economy. For the most part, however, a weak and vulnerable Havana repeated platitudes about mutual respect and national sovereignty. Its instinct to avoid grappling with the magnitude of the threat was reinforced by the United States’ involvement in Iran. If Cuba could just hold out until the U.S. midterm elections in November, officials in Havana reasoned, American voters would deliver a resounding rejection of the president’s military adventurism, and the White House would have little choice but to accept Havana’s modest concessions or simply move on.
The onus to avert catastrophe is now on Havana.
But rather than lose focus, the White House lost patience. A May 1 executive order gave the Treasury and State Departments immediate power to impose secondary sanctions on foreign companies doing business with Cuban state enterprises in strategic sectors such as mining, energy, and finance. The complex web of sanctions on Cuba, which includes a trade embargo in place since 1962, has long affected other countries’ engagements with the island. But foreign investors and operators in Cuba have never been threatened outright with losing their access to the U.S. financial system. Several companies have already paused operations on the island as a result.
Then came Ratcliffe’s visit to Havana, just a day after Cuba’s energy minister admitted publicly that the island had no oil reserves left. (Forebodingly, the CIA delegation included the leader of the Maduro capture operation.) This highly irregular overture carried a clear message to Cuba’s intelligence heads: Washington remained open to a deal, but the window was closing, and Trump’s musings about “taking Cuba” should be taken seriously. Reform the economy, release political prisoners, and (most important to the CIA) sever security ties with Russia and China, including by shutting down their listening stations on Cuban territory. Do nothing, and Havana would learn that the Trump administration’s focus on the country was not just a pet project of the president’s Cuban American secretary of state.
Finally, on May 20, federal prosecutors in the Southern District of Florida indicted Raúl Castro for ordering a 1996 shootdown of two U.S. civilian aircraft piloted by Cuban Americans over international waters, which killed three American citizens and one legal resident of the United States. The symbolism was unmistakable. For Cuban nationalists, May 20 marks the 1902 birth of the republic—but also the beginning of a post-independence order constrained by U.S. meddling. Even if the indictment was primarily intended to draw Havana to the table or to please Cuban American voters, it creates a legal pretext for U.S. military action. Recent media reports that Havana has stockpiled 300 defensive drones supplied by Russia and Iran have reinforced the administration’s argument that Cuba poses a security threat.
THE SHAPE OF A DEAL
The standard read on why Havana has refused to offer Washington more substantial concessions is that Cuban officials are stubborn or ideologically calcified. But this explanation underestimates the rationality of their position as well as the dysfunction of the island’s governance. Cuba’s leadership is not a unitary actor. Authority is dispersed across at least four overlapping centers: the still-influential Castro and his immediate circle; the military-economic conglomerate Grupo de Administración Empresarial, which controls an estimated 40 percent of the country’s GDP (and in which the Castro family holds a direct interest); the security and intelligence services; and the Communist Party and state bureaucracy.
GAESA wants to preserve its economic dominance, which would be threatened by any serious opening to the private sector. The security services want to maintain their ties with Beijing and Moscow, which any deep rapprochement with Washington would force them to renegotiate. The party apparatus fears that a meaningful political opening would accelerate the challenge to its domestic legitimacy, which is already in crisis. And Castro, a nonagenarian, views any deal that requires his exit as an existential threat to his end-of-life plans and the revolutionary project that he and his elder brother Fidel personified.
Negotiating with Washington threatens all of these constituencies. It is not surprising that they have collectively pushed back. It is also not surprising that no clear “Delcy” figure has emerged to roll over on superiors and do the United States’ bidding. What is surprising is how completely Cuba’s leadership has allowed these vetoes to drive its external strategy. Every month of gridlock further depletes the reserves, infrastructure, and social patience that any Cuban government would need to govern. The logic of resistance is intelligible. It is also a slow form of suicide.
In reality, the contours of a deal that Havana could plausibly accept have been visible for months. In March, U.S. officials told their Cuban counterparts that they wanted to see progress in strategic areas. That means liberalizing laws on free expression and association and the release of high-profile political prisoners, including those detained since the national protests that swept the island in July 2021. They are also pressing Havana to commit to broad market reforms that meaningfully open the economy to private-sector investment, including from the Cuban diaspora, and significantly reduce GAESA’s footprint.
The list of priorities also includes an agreement by Cuba to scale back intelligence and security ties with Russia and China. And because the rule of law and property protections are crucial to restoring investor confidence, Washington wants Havana to commit to working with the United States and neutral international arbiters to establish a fair, not punitive, compensation structure for resolving the morass of outstanding property claims dating from the Cuban government’s expropriations of U.S. private businesses in 1959 and 1960. These steps need not happen all at once. But if sequenced in batches, they could convince Washington that Cuba’s commitment to reform is real. They would represent the most significant internal changes in Cuba in decades, which Washington could sell as a win.
In exchange, and likewise in sequence, the United States could rescind its harshest penalties, removing Cuba from the state sponsors of terrorism list and lifting the May 1 executive order that imposed secondary sanctions. Washington could also liberalize its rules on travel to the island; allow U.S. firms back into the tourism, mining, energy, agriculture, and other sectors; and authorize investments in privately run Cuban small- and medium-size businesses. And it could suspend Title III of the Libertad Act, which serves as a major disincentive to international investment because it allows U.S. claimants to sue foreign companies operating on property that the plaintiffs owned in Cuba before those holdings were nationalized by the Castro government.
Technically, the Libertad Act conditions the full lifting of the U.S. trade embargo on the existence of a democratic transition government on the island. But if Havana matched genuine economic openings with a sufficiently reconfigured leadership, Washington might interpret “transition” creatively enough to ease sanctions, even absent full democratization. Such an arrangement would not foreclose broader political change. Rather, it would give regime leaders time to secure a mutually agreeable off-ramp while civil society rebuilds. Admittedly, the Cuban authorities have shown little interest in an off-ramp so far. But such an exit path is surely preferable to what may otherwise await them: a continued economic collapse, bringing greater social hardship and instability severe enough to prompt the United States to remove the regime by force.
This sequencing is also consistent with the administration’s instincts elsewhere, including in Venezuela: to prioritize stabilization, an economic opening, and security realignment while treating democratization as a longer-term process. The approach would likewise resonate with U.S. policy toward Cuba across several administrations—including the first Trump administration—which has tended to prioritize not the immediate fulfillment of maximalist goals enshrined in U.S. statutes but narrower objectives. These include expanding space for private enterprise, reducing the military’s grip on the economy, releasing political prisoners, loosening restrictions on information flows, and diminishing Havana’s security ties with U.S. adversaries.
NOW OR NEVER
The window for such a deal is not eternal. Consider the Rubio factor. For years, he has been one of the most hawkish voices on Cuba in American politics. That very positioning may uniquely empower him to sell a negotiated arrangement that another political figure could not. U.S. President Richard Nixon could go to China precisely because his anticommunist credentials were unquestioned. Rubio is not Nixon, and he operates under a volatile president who oscillates between isolationist disengagement and theatrical escalation. Still, if any figure in today’s Republican Party could unite Cuban American constituencies, congressional Republicans, and at least some Democrats in support of a phased and durable settlement with Havana, it would be him.
Then there is the cold reality of Cuba’s economic position. The island’s citizens simply cannot endure deepening economic immiseration under external pressure for the remaining years of the second Trump administration. Large fiscal imbalances, a heavy debt burden, and scant access to external financing mean that the government’s room to maneuver has all but disappeared. Havana may fear the short-term pain that might accompany a deeper reform process, but the truth is that this pain is already here: Cubans’ incomes have collapsed, demand for goods and services has contracted, the agricultural and manufacturing industries have withered, and the workforce has been hollowed out by migration.
The window for a deal is not eternal.
Amid the despair, there are some positive bilateral trends to build on. Cuba’s private sector, which has expanded since the legalization of small- and medium-size enterprises in 2021, now plays an important role in supporting parts of the population through the current crisis. Since the presidency of Barack Obama, every U.S. administration has identified supporting independent enterprise in Cuba as a policy priority, and even Trump is now allowing private businesses there to import fuel. This creates opportunities for more sanctions carve-outs to nurture this sector’s growth. U.S.-Cuban relations may be at their tensest in decades, but direct flights between the two countries continue, and bilateral trade in food and agricultural goods under existing embargo loopholes is setting records. Remittances from the U.S.-based diaspora are among the largest sources of hard currency reaching ordinary Cubans. An organic reconciliation between Cubans on the island and abroad has advanced further than most observers acknowledge.
Yet even a fuller opening to diaspora investment, private enterprise, and bilateral trade would not by itself generate the scale of capital needed to modernize Cuba’s crumbling electrical grid, recapitalize its banking system, or rebuild basic infrastructure. That kind of capital has historically come through the multilateral architecture: the International Monetary Fund, the World Bank, and the bilateral programs of Western governments. But funding from European governments is becoming less available as they shift resources from development aid to defense spending. Cuba cannot count on other multilateral institutions to provide emergency financing because it is not a member and cannot become one without Washington’s blessing.
The comparative cases sharpen what is at stake. In 1986, Vietnam embarked on market reforms from a position of acute crisis but with intact state capacity, a young population, and a regional economy entering its takeoff phase. In 1989, as Poland transitioned out of communist rule, its economy was collapsing, but it had inherited functional institutions and was met almost immediately by Western financing that set the country on a path that culminated in EU membership. The Cuba of today has neither Vietnam’s demographic dividend nor Poland’s external-financing pathway. Its productive base is more deteriorated, its workforce is older and more depleted by emigration, and it faces a far less generous global environment.
HISTORY’S RHYMES
Cuban leaders understandably recoil at the prospect of negotiating the island’s political and economic future under extreme U.S. pressure because doing so evokes painful historical memories. In 1901, delegates drafting Cuba’s first republican constitution faced a bitter dilemma when Washington conditioned the end of its four-year military occupation after the 1898 Spanish-American War on constitutional limits to Cuban sovereignty under the Platt Amendment. Fidel Castro and other revolutionaries would later assert that accepting those terms was a fundamental betrayal of the ideals for which Cuba’s independence fighters had given their lives in the nineteenth century.
But some of the actual delegates understood their choice less as surrender than as an attempt to preserve a fragile nation under extraordinary constraints. They sought to secure enough sovereignty to keep Cuba alive and to leave open the possibility of fuller independence later.
Cuba’s current predicament is not identical. Nor should Havana embrace economic and political reforms simply because Washington demands them. But the Cuban people deserve a viable future. And the most logical, if cruelly ironic, path the Cuban authorities can take to save their country is to negotiate with the very power inflicting grievous damage on their economy: the United States, because it is also the only one that can realistically sponsor Cuba’s recovery. Change looks increasingly inevitable. The question is whether it comes through chaotic unraveling, violent foreign intervention, or a step-by-step transformation in which Havana still has a say.
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