What Trump really wants from Cuba

In January 2026, the U.S. military captured the leader of Venezuela. In February, the U.S. and Israel killed the leader of Iran. Two of the U.S.'s top adversaries gone in just two months. But before the dust could settle, Donald Trump was already moving on to his next target. We could very well end up having a friendly takeover of Cuba. I do believe I'll be having the honor of taking Cuba. It's a failing country, and they're going to be next. The U.S. and Cuba are just 90 miles apart. Their conflict has dragged on for 67 years. Through revolution, standoffs, and crisis after crisis, neither side gave an inch. But this moment feels different. Cuba is on the brink. And Trump keeps pushing it further. I've partnered with a documentary filmmaker to take you inside Cuba. We'll explain how the country ended up in Trump's crosshairs, what he plans to do, and what ordinary Cubans see coming next. For more than a century, the U.S. has been trying to bend Cuba to its will. And Cuba has resisted. First, the U.S. intervened in Cuba. In 1898, it sent soldiers to help Cubans win independence from Spain. Then continued to prop up authoritarians like Fulgencio Batista, who obeyed the U.S. But U.S. dominance helped fuel the rise of a communist rebel, Fidel Castro, who overthrew Batista and crushed one last intervention. In less than 72 hours, Castro has destroyed the brigade. The American-backed invasion of Cuba is now a total failure. Castro seized Cuba's economy, built an authoritarian regime, and jailed thousands of dissidents. He supported left-wing movements abroad and fiercely opposed the U.S. In 1962, the U.S. changed strategies. It imposed an embargo to cut off Cuba from the U.S., blocking exports like sugar and imports like oil. The U.S. waited for Cuba's economy and regime to surrender, but it survived by turning to more sympathetic countries like the Soviet Union. For 30 years, Cuba sold the Soviets goods and bought its subsidized oil. The Soviets also helped train Cuba's soldiers and doctors. Both became some of the world's best. In 1991, the Soviets' fall sent Cuba's economy into a tailspin. But the regime adapted again by trading soldiers and doctors to Venezuela for oil, selling the services of its doctors abroad, and hosting Russian and later Chinese spies in exchange for support. These lifelines kept the regime afloat, even as ordinary Cubans struggled. Over time, the U.S. embargo, plus the regime's mismanagement, warped the economy. Cubans struggled to buy fuel and food. Hundreds of thousands fled to the U.S. every decade. Meanwhile, opposition to the embargo increased. A huge majority of U.N. countries voted in favor of ending it, year after year. But the U.S. didn't budge, largely because of politics. Cuban Americans had become a powerful block of voters determined to overthrow the regime. In the 90s, they pressured Bill Clinton to grant Congress exclusive power to lift the embargo so that future presidents couldn't do it on their own. And in the 2010s, when Barack Obama eased restrictions on trade and travel to Cuba, they fought back, especially one senator and son of Cuban immigrants. You want us to reach out and develop friendly relationships with a serial violator of human rights? It's a joke. Donald Trump agreed. In 2017, he reversed Obama's opening and tightened sanctions. Joe Biden mostly kept them in place. Meanwhile, an economic crisis led Venezuela to send less oil to Cuba. The regime found a few more suppliers. But life in Cuba got even harder. First, the pandemic overwhelmed hospitals and destroyed the tourism industry. Then fuel shortages crippled the power grid, causing blackouts, and the price of food skyrocketed. Between 2020 and 2025, as many as 2 million Cubans fled, 18% of the population. Protests erupted in Cuba. By 2025, the regime was hanging on by just these few lifelines. And as Trump took office again, he saw a chance to finally break it. First, he pressured countries to stop paying for Cuban doctors. Then he toppled Venezuela's leader and demanded the replacement stop sending oil. Then he threatened tariffs on the countries making up the rest of Cuba's supply. In his second term, Trump isn't just cutting Cuba off from the U.S. He's cutting Cuba off from everything. Now Cuba's facing its worst crisis in decades. But will it finally break the regime? So my team and I go all over the internet to report out these stories. And that exposes us to a lot of scams and spam texts. Thankfully, I keep my information safe and secure thanks to my subscription to Incogni. And they're the sponsors for this week's episode. So there are these hundreds of so-called data brokers. They take the personal information you give out on the internet, your login, your address, even your social security number, and they sell it to marketers. That's exactly how it could also end up in the hands of criminals. Now, we have the right to take this information back, but it would take forever to do it on our own. That's exactly what Incogni does for us in three easy steps. Step one is you create an account. You tell Incogni whose information you want it to remove. Step two, you grant Incogni the right to work on your behalf. It'll reach out to those data brokers and deal with it for you. Step three is you sit back and watch them do it. If any data brokers refuse, Incogni will handle it and keep you up to date all along the way. And here's the best part. With Incogni's custom removal feature, you can send in a link to any website that has your information, not just data brokers, and Incogni will handle getting it removed for you. Basically, you can just disappear from the internet. So right now, with the code SEARCHPARTY, you can get 60% off Incogni's annual plan. That's at incogni.com slash SEARCHPARTY. I've been using Incogni now for more than two years. I really do recommend it. If you want to support my work and stay safe on the internet, I recommend you go to incogni.com slash SEARCHPARTY today. Thanks again to Incogni for supporting our work. And I'll get you back to the story. A while ago, I was connected to a documentary filmmaker, Eduardo Bellino. He said he was going to Cuba. And when he landed in early April, he found Cubans struggling to get by without electricity. A shipment of Russian oil had just arrived, but it would only last about 10 days. Two days for me to bathe, three days. You have to cook for two or three days. Because you don't know when it's coming. There's no electricity. The cold doesn't give you the temperature. You can lose your food. It's crazy, but wow. Right now, we've been without water for five days. Five days. I live on the 14th floor. Trump's oil blockade got the regime to negotiate. He wants it to make economic and political changes. Their economy doesn't work. It's a non-functional economy. And the people in charge, they don't know how to fix it. So they have to get new people in charge. But Cuba's president, Miguel Diaz-Canal, is hoping Trump will accept just some economic changes. The regime recently announced that it will not accept new people in charge. It recently agreed to open up to investments from Cubans living abroad and have released more than 2,000 political prisoners. As of this video, reports say that these concessions could be the start of a wider deal. Trump lifts his oil blockade. And in return, the regime accepts U.S. investment, the return of some Cuban-Americans, and replaces Diaz-Canal with someone more obedient to the U.S. I think the plan is to find someone the United States can work with inside Cuba. Sebastián Acros is the director of the Cuban Research Institute at FIU. That person, in collaboration with the United States and in collaboration with the Cuban opposition inside and outside, will lead a transition process that will take a couple years. I think that's the plan. But a deal like this is probably not enough to truly change the regime. Diaz-Canal doesn't mean anything. He's not the real power. Your key man is probably Raúl Castro himself. Raúl Castro is Fidel's brother. He's 94 years old and technically retired. But he's Cuba's most powerful figure because he still commands the military's loyalty and rewards it well. He lets the military control GAESA, the state conglomerate that dominates Cuba's economy. GAESA runs everything from hotels to financial companies and faces little competition. In 2025, the Miami Herald published documents indicating GAESA makes billions of dollars a year and stashes it in foreign banks. That money helps keep the military loyal to Raúl and Raúl at the center of the regime. Replacing Diaz-Canal won't change that. I don't see in the current leadership that flexibility, that willingness to be the ones that guide the country into a more open model of society. And if Trump leaves Castro in power, Congress may not lift the embargo. The U.S. law says Congress can only lift the embargo if Cuba has a transition government that does not include Raúl Castro. So any deal that leaves Raúl Castro in power and the embargo in place won't do much to help ordinary Cubans. This man is a nurse, but since the regime caps how much nurses can make, he works as a private mechanic. Despite the crisis, Cuba's regime remains united and firmly in power. So while Trump is pushing for a deal, he's also threatening to revert to an old strategy — intervention. They built this great military. I said, you'll never have to use it. But sometimes you have to use it. And Cuba's next, by the way. Experts say Trump's unlikely to attack Cuba while there's war in Iran. But if he does topple the regime, there isn't a Cuban opposition ready to replace it, meaning the country could fall into an even deeper crisis. Every Cuban that spoke to Eduardo said they desperately want a way out of this crisis. Some were eager for even broader change. But many were worried that a U.S. intervention is the best way to achieve that. Cubans are trapped between a failed regime and a U.S. president determined to dominate it. They're unsure if either can deliver the change they're asking for. All right, thanks for watching another episode of Search Party. If you haven't subscribed yet, now is your chance to. I want to thank all of you that helped me out over at NewPress.com. I asked a few weeks ago when I said we were going to Cuba, I asked a bunch of you to help me understand more about the island and what's going on. A bunch of your feedback was incredibly helpful. If you want to join the conversation, head to NewPress.com. It's a new platform started by myself and Johnny and the other New Press channels. We use it to talk to you guys about our stories, to get story ideas from you, and to ask questions about your cities and your places, and in my case, your sports teams. So head over to NewPress.com right now to join for free, and I'll see you in a couple weeks. Thanks.