U.S. Secretary of State Marco Rubio gives a thumbs up as he attends a Caribbean Community (CARICOM) plenary session in Basseterre, Saint Kitts and Nevis on Feb. 25.
JONATHAN ERNST
POOL/AFP via Getty Images
What kind of “deal” should the U.S. make in Cuba?
Since last month, we’ve been hearing that Secretary of State Marco Rubio was negotiating behind the scenes with Cuba’s leadership to make a deal — President Trump’s favorite word — as the country faces a crippling energy crisis exacerbated by the U.S. cutting off oil supplies from Venezuela and Mexico.
Any agreement between the U.S. and Cuba will be considered a failure in Miami if it doesn’t directly benefit the Cuban people and frees them from nearly seven decades of oppression. Cubans need free enterprise, free speech and economic opportunities. We understand this cannot happen overnight, but it should be America’s goal.
Venezuela is, of course, the example staring us in the face.
The U.S. government removed Nicolás Maduro from power two months ago. But Delcy Rodriguez, his former vice president and now interim president, is running the show. Venezuelan opposition leader Maria Corina Machado has, so far, been sidelined along with Edmundo González, the presidential candidate she backed in 2024 when she was banned from running and is widely considered to have won the elections.
How much real change has there been in Venezuela since U.S. intervention began? Anyone watching events unfold regarding Cuba will be thinking about that.
On Friday, in a government meeting broadcast on state television, Cuban leader Miguel Díaz-Canel confirmed for the first time what the Miami Herald had been reporting: The Cuban government is engaged in talks with the United States. The talks, he said, according to the Herald, are aimed more at cooperation than confrontation, a critically important distinction.
A few hours earlier, on Thursday, there was another sign of movement: The Cuban government said it was releasing 51 prisoners as a goodwill gesture toward the Vatican. That seems like a positive indication, bolstering the idea that Cuba-U.S. relations are changing.
For Miami, this is a head-spinning time.
Yes, we have seen some of this before. Cuba has released political prisoners amid negotiations with the United States in the past, including in January 2025, when it freed 553 prisoners as “a gesture” to then-Pope Francis. That was part of a deal cut with the Biden administration, which removed Cuba from the U.S. list of nations that sponsor terrorism.
But this feels different. That’s partly because of this extraordinary juxaposition: Rubio, a Cuban American, was the one meeting with Raúl Castro’s grandson, Raúl Guillermo Rodriguez Castro, in St. Kitts last month.
Rubio’s family immigrated to the U.S. from Cuba in the 1950s. He’s from Miami, steeped in exile politics. He has long urged the U.S. to aggressively oppose the Cuban government, a government that has for decades been virtually synonymous with Fidel Castro, now deceased, and his brother, Raúl. Rubio is, in many ways, uniquely qualified for this moment.
There are questions, though — big ones. Miami-Dade Commissioner Natalie Milian Orbis issued a press release Friday, titled, “Any deal that keeps Cuba communist is unacceptable.”
She lauded the negotiations, giving the president credit for restoring pressure on Cuba and forcing its government to the table. And then she raised this point: “As long as the regime refuses free and competitive elections, continues jailing and persecuting dissidents, and refuses to recognize lawful property rights, the United States must not legitimize or finance its oppression.”
U.S. Rep. Mario Díaz-Balart said it a couple of days ago in a Herald story: “Partial changes are not acceptable; the concept of Raúl without Raúl is not acceptable to this administration.” He was referring to the idea that other members of the Castro family could remain in charge of the country.
We hope those kinds of doubts do not cripple progress in Cuba. And this is a unique time. Cuba is weak.
Díaz-Balart told the Herald that the Trump administration has been having conversations with several people in Raúl Castro’s close circle. Rubio, meanwhile, has been careful not to raise hopes of sweeping change, a wise way to manage expectations.
“Everyone is mature and realistic here,” Rubio said in a press conference last month in Saint Kitts on the same day his team met with Castro’s grandson.
Trump and Rubio may be on the right track for Cuba. But in Miami, where Cuba has loomed large in politics for decades, real justice and freedom is still the most important goal. That will be the real art of the deal for the Trump administration.
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