Trump aims to end the revolution that Fidel Castro started. Can the US and Cuba strike a deal?

2026-03-22 - 08:20

Havana — Donald Trump wants us to believe that a deal with Cuba is close at hand. After this past week, I am not so sure. “They have no energy. They have no money. They’re in deep trouble,” Trump has said, explaining why he believes the Cuban government is desperate to reach an agreement to save the country. Trump is correct that Havana is under the most severe pressure at any time since the 1962 missile crisis, when a US invasion of the island seemed all but guaranteed. Now, as back then, Cuba faces a US blockade. Through military action in Venezuela and threats of tariffs on Mexico, Trump has prevented oil from entering the island, crippling an economy already hamstrung by the communist government’s own disastrous limits on private industry. Trump’s secretary of state, Marco Rubio, a Cuban American and a fierce critic of the island’s leadership, is leading negotiations with Havana. He has been preparing his entire professional life for this moment. In mid-January – as Cuba received the bodies of their 32 soldiers who died defending Nicolás Maduro during the US attack that captured the Venezuelan leader – I heard Cuban President Miguel Diaz-Canel vow at a mass demonstration in front of the US Embassy in Havana that the government would make no concessions to the Trump administration. But then, as the oil blockade took a toll on already beleaguered Cubans, signs of an agreement began to emerge. After weeks of rumors and leaks in Washington, Cuba confirmed negotiations were being held. The government released 51 prisoners, some of them jailed for protesting against the administration, and announced long-awaited, if still limited in scope, reforms that would allow Cubans living abroad to invest on the island. Rocking back and forth nervously during a television appearance, a haggard-looking Diaz-Canel acknowledged the same talks, which his government had denied were taking place just days before. “Whenever we have been in tense situations in relations with the United States, efforts have been made to find channels for dialogue,” he said. Then just as quickly as negotiations were confirmed, Trump seemed to squash any chance they would lead anywhere. The ‘honor of taking Cuba’ On Monday, as Cuba endured a nationwide blackout, Trump, alongside Rubio in the Oval Office, declared: “I do believe I’ll be having the honor of taking Cuba. It’s a big honor, I ​mean, whether I free it, take it. I think I can do anything I want with it.” Rubio appeared to confirm earlier reports in The Miami Herald and The New York Times that the administration was demanding that Diaz-Canel and other officials viewed as obstacles to change step down. US President Donald Trump walks with US Secretary of State Marco Rubio as he departs from the South Lawn of the White House in Washington, DC, on Friday, March 20, 2026. Brendan Smialowski/AFP/Getty Images “The people in charge, they don’t know how to fix (Cuba’s economy),” Rubio said. “So they have to get new people in charge. That’s what has to happen.” Trump mused as well about Cuba’s “great weather” while bizarrely and falsely asserting that the island, just 90 miles from Florida, is “not in the hurricane zone.” The comments played into the hands of Cuba’s hardliners who have long claimed the ultimate goal of the US is to annex their island. The Cuban government soon fired back at Trump’s assertions, with Diaz-Canel posting on X: “In the face of the worst scenario, Cuba is accompanied by a certainty: any external aggressor will clash with an impregnable resistance.” Letting the US pick who leads the island was tantamount to surrender and would not be considered, officials said. “Neither the president nor the position of any leader in Cuba is up for negotiation with the United States,” Cuba’s top diplomat for US affairs, Carlos Fernández De Cossio, told reporters in Havana on Friday. Cubans have now been treated to the surreal sight of the island’s most famous living musician, Silvio Rodriguez, receiving a machine gun alongside the Cuban president and top military officials. Rodriguez, a stalwart supporter of the revolution who is sometimes called “Cuba’s Bob Dylan,” has criticized Diaz-Canel’s management of the economy in recent years. But on Friday, he was all in. Cuban folk singer Silvio Rodriguez, standing near Cuban President Miguel Diaz-Canel, is presented with an AKM war rifle and a ceremonial replica by Minister of the Revolutionary Armed Forces Army Corps General Alvaro Lopez. Cuba Presidency/Handout/Reuters “I demand my AKM, if they launch an attack. And I mean it,” the musician, 79, posted online, referring to the rifle that replaced the AK-47 and is standard issue for the Cuban military. Rodriguez, whose songs about love, social justice and human connection have reached millions over the decades, had requested the weapon to defend the island, according to state media. Trump’s threats and the oil blockade seem to have united Cuban officials and supporters of the government at the same time his administration was trying to splinter its inner circle. “The (Cuban) government’s claim that it’s the US embargo that’s at fault was wearing a little thin, because they’ve been making that argument for many, many years,” William LeoGrande, a professor at American University, told CNN. “It’s true, of course, that the US economic embargo does hamper the Cuban economy tremendously, but people were beginning to blame the government’s mistakes.” Keep talking — and buying time Despite the rising tensions and Trump’s belligerent comments, Cuban officials said they would continue with negotiations. “We will also be open to a serious and responsible dialogue with the government of the United States, without interference in internal affairs or in our respective political, economic, and social systems,” Foreign Minister Bruno Rodríguez Parrilla said Saturday at a forum for Latin American, Caribbean and African countries. The Cuban strategy appears to be keep talking to buy time, perhaps even until the US midterm elections in November when the Democrats could regain Congress. It’s not clear how much time they really have — both Venezuela and Iran were in discussions with the US when Trump ordered attacks on those countries. Bruno Eduardo Rodriguez Parrilla, Cuba’s foreign minister, during the United Nations General Assembly in New York, on September 27, 2025. David Dee Delgado/Bloomberg/Getty Images And there are reports that the Trump administration may indict former Cuban leader Raul Castro – who still wields ultimate power on the island – for his role in the 1996 Brothers to the Rescue shootdown and decades-old allegations of involvement in drug trafficking which the Cuban government has long denied. Any US charges against Castro, 94, would likely kill off any chance of a diplomatic solution. Initially, Trump had seemed to propose an economic opening that some Cuba-watchers called Obama 2.0, in reference to the agreement that Trump’s predecessor negotiated but that was scuttled after he left office. Now it’s clear, despite whatever promises of sanctions relief or side deals Trump is promising to Cuban officials, his aim is to end the revolution started by Fidel Castro. But for many Cubans any benefits afforded to them by the island’s socialist system vanished long ago. A government food-rationing system now delivers only the most meager supplies, the island’s vaunted medical and education systems have been dramatically reduced, blackouts stretch across most the day and whole neighborhoods are buried under uncollected trash. People walk on a street during a blackout in Havana, on Monday, March 16, 2026. Ramon Espinosa/AP “It’s like we are not people, we are animals! What a lack of respect. Tourist areas are cleaned but here no. It’s sad,” Centro Habana resident Joani Manuel Tablada Fal told CNN on a street where trash stretched knee-deep for more than a block. Frustrated at worsening conditions, Cubans on a nightly basis are taking to the streets to participate in forbidden protests beating pots and pans to call for change. While the Trump administration promises a quick deal and the Cuban government prepares for invasion, it’s possible neither scenario will take place. Instead, left under the most punishing economic sanctions Cubans have known in their lives, the island may slowly wither and die.