Key Points
— Cuba’s ambassador to the United Nations, Ernesto Soberón Guzmán, told the Associated Press that the island will not accept any Trump administration ultimatum to release political prisoners as a condition for further talks. The two-week deadline that Washington reportedly imposed during the April 10 meeting in Havana expired Friday, April 24, without a response from the Cuban government. The Cuba US ultimatum lapsed quietly while both sides continued to dispute whether the deadline ever existed.
— The State Department had specifically demanded the release of two prisoners held since the July 11, 2021 protests: artist Luis Manuel Otero Alcántara and rapper Maykel Osorbo. Soberón said internal detainee matters are “not on the negotiation table” and added that Cuba is “preparing for all scenarios” if Trump follows through on threats of military action. The Cuban legal system, he said, deserves the same respect Washington demands for its own.
— The standoff plays out against acute energy collapse on the island. A Russian tanker carrying 730,000 barrels of crude that arrived in late March was the first fuel shipment Cuba had received in three months, after Mexico’s Pemex suspended deliveries and Venezuela cut subsidized supply following the US capture of Nicolás Maduro in January. Trump’s January 29 Executive Order 14380 declared Cuba an “unusual and extraordinary threat” and authorized secondary tariffs on any country supplying it with oil.
The Cuba US ultimatum has expired without a deal — and Havana’s public message is that the political prisoners Washington wants released will not be part of any negotiation, even as the island’s energy crisis deepens and Trump weighs his next move.
The first round of direct US-Cuba diplomacy in a decade has produced its first standoff. The Rio Times, the Latin American financial news outlet, reports that the Cuba US ultimatum imposed by the Trump administration during the April 10 secret meeting in Havana expired Friday with no movement from the Cuban side, leaving the two governments locked in public disagreement over what the deadline even covered.
Cuba’s UN ambassador Ernesto Soberón Guzmán used an Associated Press interview Thursday to set the boundary publicly. Internal matters about detainees are not on the negotiating table, he said, and Havana will respond to any military action if Trump follows through on his recent threats. The Cuban diplomat framed the position around legal sovereignty rather than ideology.
What the Cuba US Ultimatum Actually Demanded
According to reporting in USA Today and Axios that the Cuban government has not confirmed, the State Department gave Havana two weeks to free a specific list of political prisoners. At the top of that list were artist Luis Manuel Otero Alcántara and rapper Maykel Osorbo, both jailed since the July 11, 2021 mass protests — the largest anti-government demonstrations in Cuba since the revolution.
The two artists carry symbolic weight inside and outside the island. Otero Alcántara is a leader of the San Isidro Movement; Osorbo co-wrote the protest anthem “Patria y Vida” that became the soundtrack of the 2021 demonstrations. Their continued imprisonment has been a recurring point of pressure from human rights groups and the European Union.
Soberón did not confirm or deny the existence of the deadline itself, telling AP only that the underlying demand was unacceptable. The State Department responded with a statement reaffirming its commitment to “the release of all political prisoners” and warning Cuba that it has “a small window to make a deal” — the closest Washington has come to confirming the two-week framing.
The April 10 Meeting and the Castro Channel
A US delegation flew into Havana on April 10 — the first official US government aircraft to land in Cuba since 2016. Talks were held at the subsecretary level on the US side and the deputy foreign minister level on the Cuban side, neither government has named the participants. The US side discussed compensation for property confiscated after 1959, the introduction of Starlink internet on the island, and reforms to attract foreign investment.
Washington also confirmed a separate, private meeting between a senior Trump administration official and Raúl Guillermo Rodríguez Castro, the grandson of Raúl Castro. That parallel channel has fueled speculation in exile circles that the dynasty is positioning to outlast the formal government of President Miguel Díaz-Canel.
Soberón confirmed that property compensation for Cuban-Americans was on the table and that Havana is receptive to it. But he conditioned any deal on reciprocal relief from the US embargo, calling the issue “a two-way street” rather than a unilateral concession. Díaz-Canel told Brazilian journalist Breno Altman in a separate interview for Opera Mundi that political-system change is “absolutely not” up for discussion.
Energy Collapse Sets the Backdrop
The leverage Washington brings to the table comes from physical scarcity on the island. Trump’s Executive Order 14380, signed January 29, declared Cuba an “unusual and extraordinary threat” and imposed secondary tariffs on countries supplying the island with crude oil. Pemex suspended Mexican shipments soon after, and Venezuela’s subsidized supply collapsed when the US captured Nicolás Maduro in early January.
The result has been months of rolling blackouts, hospital disruption, and food shortages on an island of 9.6 million people. The Russian tanker that docked in late March with 730,000 barrels was the first fuel arrival in three months. Soberón told AP the cargo covered only a fraction of the island’s needs.
Russia announced a second tanker is being prepared. The secondary-tariff threat against oil suppliers was partially walked back after a US Supreme Court decision narrowed the scope of the executive order, but the underlying energy blockade remains in force as the central element of US pressure.
Rubio, Trump, and the Threat of Force
Secretary of State Marco Rubio — the son of Cuban immigrants and the architect of the administration’s hardline posture toward Havana — has insisted publicly that Cuba’s economic problems cannot be addressed without changing the political system itself. The State Department has restated that position consistently since the April 10 meeting.
Trump has been characteristically blunt. He said earlier this month it would be “an honor” to “take Cuba” and pointed to post-Maduro Venezuela as the operational template, after the US military operation that removed Maduro from Caracas in January. Soberón told AP that Cuba “is not naive” and is “preparing for all scenarios,” including a military response if necessary.
Time magazine’s April 23 cover captured the mood, depicting falling dominoes with the Cuban flag as the last one standing under the headline “What will become of Cuba, as the island awaits Trump’s end game?” The visual encapsulates how the bilateral standoff is being read across the region.
Where the Standoff Goes Next
The expired ultimatum leaves both governments in a controlled escalation. Washington’s “small window” warning suggests further sanctions tightening rather than immediate kinetic action. Havana’s “all scenarios” framing leaves room for additional concessions on property compensation and foreign investment without crossing the political-prisoner line.
The Castro grandson channel — separate from the official government track — is the wild card. If the Trump administration concludes that a usable Cuban interlocutor exists outside the Díaz-Canel government, the calculus on military pressure shifts. Until then, the public-facing standoff over the political prisoners holds.
For Latin American capitals watching the Cuba file, the message is the same one delivered earlier in the Maduro operation: the Trump administration will set deadlines, and it will let them lapse without retreating from the underlying demand. The next move belongs to Washington.