Even as U.S. President Donald Trump vows to usher in a “new dawn” for Cuba, possibly through military force, his administration is pursuing high-level diplomatic talks that seem to be producing some concrete results.
Over the weekend, the New York Times and AP confirmed reporting by Axios that a U.S. government plane with a senior State Department delegation landed in Havana on April 10 for direct talks with Cuban officials, as well as a side meeting with Raúl Castro’s grandson, Raúl Guillermo Rodríguez Castro, known as “The Crab.” These discussions reportedly addressed prisoner releases, economic reforms, internet connectivity, property claims and political freedoms on the island.
USA Today added late Sunday night that U.S. officials gave Cuba a two-week deadline to release high-profile political prisoners, including artists Luis Manuel Otero Alcantara and Maykel Osorbo of the dissident San Isidro Movement, as a gesture of good faith amid a “small window” to make a deal before the island’s humanitarian crisis deepened. On Monday, an official in Cuba’s foreign ministry confirmed these talks, calling them professional and respectful and adding that no deadlines were set nor threatening statements made by either side. The State Department confirmed that Secretary of State Marco Rubio did not visit the island without clarifying who did. Cuba, for its part, said the meetings took place between its vice foreign ministers and U.S. “assistant secretaries,” likely referring to Michael Kozak, the senior bureau official for Western Hemisphere Affairs, and potentially his counterparts in other State Department bureaus as well as the Departments of Homeland Security and Justice.
The discreet meeting in Havana appears to be the highest-level U.S. government delegation to visit Cuba since President Barack Obama’s historic 2016 opening to the island. Not long after, the first Trump administration rolled back Obama’s efforts to fully normalize bilateral relations despite near-unanimous support for the efforts from Trump administration deputies at the Departments of Commerce, Defense, State, Treasury, Agriculture and Homeland Security.
Under the Biden administration, senior State Department and National Security Council officials received top Cuban officials in Washington, and two deputy assistant secretaries of state , as well as an assistant secretary for consular affairs, visited the island. But it’s been a decade since a U.S. delegation of this seniority has visited the island for such wide-ranging talks.
Kozak has been negotiating with Cuban authorities for decades, most famously using a pseudonym for talks in the mid-1980s with Cuban authorities in Manhattan, before serving for three years in the mid-1990s as the head of the U.S. Interests Section in Havana during a particularly tense moment in bilateral relations under the Clinton administration.
At a House Foreign Affairs subcommittee hearing last Thursday, Ranking Member Joaquín Castro (D-TX) pushed Kozak for more information about the talks. But Kozak refused to identify who in the administration was taking part in the negotiating or with whom they were talking.
“The reason that’s so important for us to know is because the president might launch a war with this country, and I want to know if there’s a chance we’re going to avoid that or not,” Castro said.
“We’re engaged with them,” Kozak told the subcommittee. “What will happen, it remains to be seen.”
Axios broke the news of the “historic negotiations” on Friday, quoting an unidentified State Department official as saying, “President Trump is committed to a diplomatic solution, but will not let the island collapse into a major national security threat.”
The meeting comes amid the administration’s near-total fuel blockade of the island, which has caused preventable deaths, brought public transportation to a halt, exacerbated island-wide blackouts and provoked what many Cubans consider an “ untenable ” situation, particularly for public sector workers and those without family living abroad.
“Lifting the energy blockade against [Cuba] was a top priority for our delegation,” a Cuban foreign ministry official said . “This act of economic coercion constitutes an unjustified punishment of the entire Cuban population [and] amounts to blackmail on a global scale against sovereign states, which have every right to export fuel to Cuba under the rules governing free trade.”
In late March, amid the war in Iran, the Trump administration seemingly eased up on Cuba by allowing a Russian crude oil tanker to reach Havana. Another one is slated to arrive late next week. The month before, U.S. authorities sent $6 million of humanitarian aid to eastern Cuba and authorized private sector firms to import fuel to the island, including from Venezuela . Fuel traders in Miami are reportedly seeking a U.S. license to provide diesel to Cuba’s sanctions-battered public health system, which Kozak confirmed would be a way to support Cuban civilians.
Cuba, for its part, has released political and common prisoners through Vatican mediation and a mass amnesty , loosened restrictions on private enterprise, and made overtures to its diaspora in the U.S.
On Monday, in a sign of ongoing law enforcement cooperation between the two countries, a Justice Department plane quietly flew to Havana to recover a minor who the F.B.I. believed to have been kidnapped by a parent to undergo gender transition surgery on the island.
The surprise mission came on the heels of a rare FBI visit to the island to investigate a shoot-out off Cuba’s coasts in late February in which an armed U.S. citizen and five other Cubans residing in the U.S. were killed.
While the U.S. says it has no “specific, imminent operations against Cuba under consideration,” USA Today reported last week that the White House ordered the Pentagon and other agencies to expedite preparations for military action on the island. Last Thursday, a U.S. Navy surveillance drone conducted an unusual reconnaissance mission around Cuba. Cuban President Miguel Diaz-Canel, meanwhile, has repeatedly promised to resist any U.S. attack through guerrilla warfare.
In an effort to pre-empt a U.S. attack, Sen. Tim Kaine (D-Va.) is teeing up a war powers resolution vote for early next week, according to congressional aides who spoke with RS.
Even with the tough rhetoric from both sides, it appears a comprehensive deal similar to the one RS outlined in February may be taking form. In bilateral talks, including a meeting on the sidelines of the CARICOM Summit in St. Kitts and Nevis in late February, the U.S. has urged Cuban leaders to release prisoners, pursue market reforms, and provide compensation to owners of properties nationalized after the 1959 Cuban revolution. Cuba, for its part, has said it is ready to negotiate on these points in exchange for oil exploration and infrastructure investments by U.S. and Cuban American-owned firms, partial sanctions relief , and greater cooperation with the U.S. on law enforcement and security matters.
Rubio and the hardline anti-communist leaders in South Florida’s Cuban-American community that catapulted his rise to power would likely object to any deal that doesn’t require root-and-stem political changes. But the other available options — issuing tighter sanctions, launching a military campaign, or doing nothing at all — are all political minefields for the Trump administration heading into the midterm elections this November.
“I don't think anyone should be surprised if we eventually see Steve Witkoff and Jared Kushner in Havana negotiating [a deal] with the Cuban government," John Kavulich, president of the U.S.-Cuba Trade and Economic Council, told USA Today.