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........

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