Today, Explained - Cuba, too

Episode Date: May 26, 2026

Cuba seems willing to concede more than ever if the Trump administration is willing to take the win. This episode was produced by Peter Balonon-Rosen and Danielle Hewitt, edited by Amina Al-Sadi, fact-checked by Gabriel Dunatov, engineered by David Tatasciore and Bridger Dunnagan, and hosted by Sean Rameswaram. A rally in support of former Cuban president Raul Castro outside the US Embassy in Havana. Photo by ADALBERTO ROQUE / AFP via Getty Images. Listen to Today, Explained ad-free by becoming a Vox Member: vox.com/members. New Vox members get $20 off their membership right now. Transcript at ⁠vox.com/today-explained-podcast.⁠ Learn more about your ad choices. Visit podcastchoices.com/adchoices

It was about a week ago that the Trump administration took maybe the boldest action against Cuba that we've seen since the end of the Cold War. An indictment of Raul Castro, brother of Fidel, that's a big deal. And then the biggest question became, are we about to invade Cuba? What is the president planning? What does his long weekend look like? People kept asking Trump if he was going to attend his large adult son's wedding. Person who I've known for a long time. And he was like, probably not?

Uh, he'd like me to go. And then he definitely didn't go, so people were like, here we go. Cuba's next. But then that didn't happen either. In fact, the United States started bombing Iran again. But Cuba's still in a tough spot. Arguably, the toughest spot it's been in since the Castoros took over in 1959. So we're going to ask what could happen next on Today Explained.

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Tap in with us. I'm in Hsuciano Aoi Expliqaidt. Patrick Otman is CNN's Havana Bureau Chief. I am in Havana right now, yes. What's going on in Havana right now? So, you know, most of this island,

most of the time, is in a blackout. And even if you had a generator, there's absolutely no oil to be had. When I could find gas here, it costs about $300 to fill up my car. Wow. You know, before you had really long lines. of the gas station. Now there are none because there's just no gas to be found. So, you know,

I have about a quarter of a tank once that's up. I'm not sure what I'm going to do. And on top of all of that, revolutionary Raul Castro was indicted by the United States a few days ago. Yes. So this is last week. Raul Castro is the former president of Cuba, but that really doesn't do him justice. He's still very much the most powerful man at 94 years old on this island. So 30 years ago, there was an incident where you had. Cuban American planes that initially started out trying to spot Cuban rafters in the water, trying to escape Cuba by raft. And then they transitioned to this mission, which of course

they should have known was going to end badly, where they were flying into Cuban airspace and scattering leaflets. And the Cuban government warned the U.S. many times during the Clinton administration, stopped them from doing this. It's really angering us, violating our airspace. And then finally, they were shot down. The Clinton administration is calling for an emergency session of the United Nations Security Council after two civilian aircraft were shot down by Cuba yesterday.

The aircraft were part of a routine private search and rescue operation in the Florida Straits. A third plane, flown by brothers to the rescue founder Jose Basulto, managed to escape the attack. Smoke, ball, perhaps even fire in it to our north side of our aircraft, perhaps seven miles away from where we were. And after that, there was complete silence from both aircraft. There was kind of a warning given, and these are planes that were unarmed, and that led to an increasing U.S. economic sanctions.

Castro's Air Force shot down two civilian planes belonging to a Cuban exile group in Miami. President Clinton retaliated by signing the Helms-Burton bill into law. bill into law. Finally, let me say, as I sign this bill into law, I do so in the name of the four men who were killed when their planes were shot down, Armando Alejandro, Carlos Costa, Mario de la Pena, and Pablo Morales. And for many years and many administrations, because Raul Castro was head of the military then, the defense minister, many U.S. administrations have kind of thought about indicting Raal Castro for this, and most of them thought, you know, two,

long ago it is a sovereign state and they have the right to protect their country. It happened in international waters is what the U.S. has always said. Today we are announcing an indictment charging Raul Castro and several others with conspiracy to kill U.S. nationals. So the Trump administration took this extraordinary step of indicting a former sitting leader of our country. And this is obviously part of this pressure campaign, trying to get the Cuban government to make major political concessions, major economic concessions, which so far the government here has resisted. Some of the people listening to this right now surely weren't even born

during the Clinton administration. Why bring this indictment now? Is it so that the Trump administration has grounds to go in and depose the leadership in Cuba or something of that sort? They're clearly following the same script that they used with Venezuela, which they would say they used to great success. They installed in Venezuela a government that's a lot more friendly to U.S. interests that is responding when they make demands, and they would like something very similar for Cuba. The current model they have is it's not just, it's broken, it doesn't work,

and it'll never change as long as the people that are there now are running it. They are closed-minded, unfortunately. And what the Trump administration has said is there's an easy way to do this, which is we tell you what policies to make, and there doesn't have to be democracy overnight, and there doesn't have to be, you know, a change in leadership necessarily. The Castro could stay, but, you know, you'd open up your country, you need to allow Cuban Americans to come back and invest freely. Cuba is surrounded by places where people have the right to do things like own a business,

work for themselves, and be able to vote and for the leaders that govern them and or replace them. So if that's possible all around Cuba, why is it impossible? Why is that not possible inside of Cuba? And, you know, we need to see some changes in terms of foreign policy as well. You need to kick out the Russians and the Chinese who the U.S. alleges have spying bases here, spying on the U.S., you know, stop allying with countries that don't have our same interests in mind. And the Cuban government has said, you don't get to tell us what to do. You know, the whole point of having a revolution is that we decide our own destiny. And so you've seen a ratching up of pressure. And the latest step in that has been indicting Raal Castro. And I think

this is the best case they had. It's certainly a long time ago. But it gives them the opportunity to say, okay, the next step is we try to come and get Raul Castro like we did with Nicholas Maduro. And if you don't think, you know, we can, you're in for a nasty surprise. Nicholas Maduro currently resides in Brooklyn at the Metropolitan Detention Center. Is that the plan for Raul Castro, who's not in power technically and is even older than President Trump. He's 94 going on 95 momentarily here? Raul Castro is 94. We saw him on May Day, which of course has a lot of significance in Cuba.

And, you know, he looks exactly what you'd expect someone at 94 to look like. And so are you really going to send in the U.S. Special. forces, you know, that have to bring a wheelchair with them, I think. Is it worth it? It's such an extreme policy in that, you know, you're obviously risking U.S. lives. Beyond that, you're also risking the potential, which has happened so many times in the past in Cuba, which is you spark a migration crisis. The Cuban government, for all its faults, has said that they want to negotiate, they want to sit down and that they're open to make certain changes to their system without their needing to be military action. Clearly, the Trump

administration just does not feel that they are operating in good faith. And I think there are people in the Trump administration who simply see this is quicker, this is easier, and we'll get what we want, which is regime change. One thing I wonder comparing this situation in Cuba to the one in Venezuela that we've referenced a couple times, would Raul Castro, you know, in a Nike track suit, just let the United States wheel him onto a plane and end into MPD in Brooklyn? or, I mean, would this be like a cyanide situation? They've said here they will not get him alive, certainly because he's the ultimate figure here.

He represents the Cuban Revolution. He's the only Castro that's alive that was around when the Cuban Revolution took place. And so they will put up resistance. I think Raal Castro probably is sleeping with a gun next to his bed. He's probably told his bodyguards, don't let them take me alive. But here they're treating it very seriously

because Nicolas Maduro is one of their closest allies. They see where he is now. And they see, you know, this isn't just the U.S. saying this to win Florida in an election every four years. You know, Trump really means it. And they are prepared to go through with it. So it's a level of pressure. People have never seen here, never felt here.

There are protests happening against their own government with greater regularity than we've ever seen really before. And so there's just a tension. and certainly on the U.S. side, you can't discount anything that they're threatening to do because they've already done it. We had the head of the CIA here just this month, and he delivered a very hard message in terms of, you know, do this or else. Ratcliffe conveyed a message from President Trump. The U.S. is willing to work with Cuba on economic and security issues, but only if Cuba's communist government makes fundamental changes. Ratcliffe putting pressure on Cuban officials to stabilize the country's economy.

and work with the Trump administration on security and economic issues. I mean, what's the vibe out there? It's been almost a week since this indictment. Do people feel like this is the end? People feel that it's really going to happen now. I think the fact that a former president of theirs, who's named Castro, has been indicted. I think that's the clearest sign that there is going to be military action.

We've really seen the Cuban officials sort of shut down in terms of talking about negotiations, of talking about, you know, finding a solution to this. I've heard about them passing out guns to people who are not military, but are trusted people, you know, in the Communist Party and saying, okay, you know, here's a pistol. And if you've seen an American soldier, shoot them. But, you know, when you're dealing with power outages,

and it's not a one-time thing. It's every day that are 20, 22 hours, sometimes stretching several days. you know, it's like you're living in a different century. It's no way to live. Everyone looks kind of looks like a zombie these days. All we talk about here amongst my colleagues, my friends, Cubans who are friends of mine, is like, is this really going to happen?

How would it play out? Is it a limited engagement like we saw in Venezuela? Or is it something much larger? Because if you not got the government here, then you're kind of just dealing with another failed state in the Caribbean like Haiti, and who picks up pieces of that failed state, particularly one where everything is broken down

over the last so many years since the fall of the Soviet Union. Cuba needs a ton of investment, and it's not clear who's going to step up and put the billions of dollars in this island that they would need to have a working power grid and other things like that. It certainly doesn't appear to be the Trump administration that has always been against kind of nation building,

and they would need a lot of nation building here, particularly if you took out the government that, while it's barely functioning, it's still functioning, it's still running the show here, and it's the only government that anyone, who's here has ever known. Feels like regime change could go one of two ways in Cuba. We're going to weigh the pros and cons of each when today explained is back.

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With Shopify today, you can sign up for your $1 per month trial today at shopify.com.com slash explained. You can go to shopify.com slash explained. Today, explained. My name is Cecile Shea, and I am a retired Foreign Service Officer, currently a non-resident senior fellow at the Chicago Council on Global Affairs. Great. I want to ask you about some affairs that are kind of close to home, depending on where you live in this big country of ours, Cuba. Secretary of State Marco Rubio posted a video last week about Cuba.

Did you watch it? I did watch it. What do you say? He spoke Spanish. Of course, he's a Cuban American. And he said, listen, Cuban people. It's not the United States fault that you don't have any. that your electricity grid is down. No, it's a blocker of petrolero

for part of the United. It's the fault of mismanagement by your government. Don't blame us. It's not because of our embargo. It's because you are badly led. The real reason for that not have electricity, combustible, or animals is because who controls their country.

And it's time for you to pressure your government to step down. The only that's interpone in the the way to a better future are who controls their country. That's a paraphrase, but that's generally what he said. Is that generally true? No, it is not generally true.

There is truth to it in that, yes, the government has not always been a great government. It has a closed economy. But the reason certainly that Cuba is in the current crisis, which is that there is no oil at all for consumers or businesses, they've reserved some for hospitals and the like. But the reason for this is the U.S. is forcing that. Venezuela not to ship oil to Cuba. Since U.S. President Donald Trump severed the island's access to its primary petroleum sources in Venezuela and Mexico, the Cuban government has brought in emergency measures to ration what fuel is left and ease blackouts.

They're affecting everything from homes to hospitals. Cuba's at the end of the line. They're very much at the end of the line. They have no money. They have no oil. Now for the last 50 years or so, the U.S. has ensured that no country, other than a couple that the U.S. didn't help sway with, such as Venezuela, we insisted that other countries not export oil to Cuba. So now that Venezuela is also not

exporting oil to Cuba, it means that they're out of oil. And that's completely on us. And anyone in Cuba listening to Marco Rubio's speech would have known that. What does make this moment different? Is it that this administration is willing to go further than than previous ones? What could be interesting about this moment is that Cuba seems ready to deal. Truth Social. No Republican has ever spoken to me about Cuba, which is a failed country and only hedging in one direction. Down! Cuba is asking for help, and we are going to talk.

In the meantime, I'm off to China. If we believe the press reports, and again, they're just press reports. But if we believe the press reports, Cuba has offered children. to release political prisoners, which would be huge because it would create a political opposition in the country. Cuba has agreed to open its economy. Cuba has agreed to allow Cuban exiles to invest back into Cuba.

I mean, things that we have been asking for for decades, it now appears that Cuba is willing to do. And I wish we would take the win. You know, I wish we would accept these things and then add something to it. We want you to promise to have a free and fair election two years from now. that would just make so much sense

and we wouldn't be talking about the military and we wouldn't be talking about going in and kidnapping 93 or 94 year old men and and President Trump could be finally be what he wants to be he wants to do what every president since Eisenhower has wanted to do

which is and the kind of communist oriented regime that we have in Cuba you know Eisenhower tried JFK tried Trump was alive during the Cuban Missile Crisis He was an adult. I'd be hearing about Cuba. So was Biden.

Come on, man. This is all very real personal history to them. And I do think that part of what is going on is Trump wants to be the president who can accomplish what no other president has done. And I happen to think he could be. I don't think it's going to be through a military method. I mean, to be sure, he has the attention of the people in charge of Cuba. We have a lot of leverage there.

And the government seems, the government of Cuba seems willing to listen. to us and to do some of the things that would keep us happy. And that's particularly true of the younger generation in Cuba. I think they would like to see the government open up relations with the U.S. and kind of move beyond revolutionary Cuba and some of the sloganeering. Okay, so the Cuban government is willing to concede in a way we haven't seen in decades. Young Cubans want there to be an opening up of Cuban society. They want the government to play ball, and yet it sounds like you're saying it's more than likely the Trump administration will not go for it? Unless there's a lot going on behind the scenes that nobody sees, it seems like there would

be a lot more talking and taking the win right now, especially if the Cubans actually did offer the things that the press has been reporting. I don't understand, for instance, the indictment against Raul Castro. He wouldn't still be alive by the time the trial would start. And he and his family are still heroes in Cuba, particularly with the older generation. So why mess with the Castro's? Can I offer a theory? Yeah, please do. Is it what the diaspora wants?

So that's a good question. And is it in particular what the older diaspora wants? In part because of pressure from us, Cuba began allowing more people to emigrate from Cuba over the last 20 years. And a lot of them came to the U.S. And there's some evidence that among that million, million and a half or so emigres, they really want to move forward. They're really not interested in fighting the wars of the 1960s anymore. I think we've heard your best case scenario, Cecil, that the United States takes concessions from Cuba and allows the country on its own terms to transition to free elections that, you know, organically replaces the Castro regime. What's the worst-case scenario here?

So the short-term worst-case scenario is that we end up with something worse than we have now. The long-term worst-case scenario is that we further alienate the Cuban people who have already suffered from our sanctions and our embargoes for the last 60-some years. And it harms our ability to create a close relationship with a country 90 miles away

over the next 20, 30, 40 years. It's hard for politicians to look past the next election. It's one of the weaknesses in our government. But we should also be thinking about what kind of relationship we went Cuba 15 years from now. And invading the country is not a way to make the odds of having a good relationship in the future strong. I mean, you keep talking about this conflict, this tension between the United States and Cuba as something from another generation, like a holdover from the 60s. and 70s, the Cold War. I mean, I feel like most Americans right now

are not thinking about Venezuelan or Iran nor Cuba. They're thinking about their gas prices and interest rates. How should Americans be feeling about this intervention that we may soon be executing on this island? Here's what I would say to some of those Americans. Imagine we could go two routes right now. Imagine we could start selling space. parts that Cuba desperately needs to keep their machines running.

Imagine we could make an agreement with them that would allow them to begin importing America vehicles again, tariff-free. Imagine that you could take vacations to Cuba again, which are fairly inexpensive. Would you choose all of those things? Or would you choose sending more young people into Harmsway 90 miles away from Florida? even more of a pariah in the world than we already are. Because if you've been to Europe lately or Canada lately, you know that Americans are very unpopular right now

and just imagine what will happen if we take military action in Cuba. I think we should also talk about the morality of the situation. There are people who can't get kidney dialysis right now because the hospitals are running out of oil. There are people who can't get to work and therefore can't get paid because they can't put gas in their vehicles. These people are just 90 miles away from us.

Are we really going to let this kind of pain and suffering continue through the hottest part of the year? And what will be the long-term harm, not only to them and to their health, but to their views toward the United States, we should not just be sitting by and watching this happen. That was Ceil Shea. She's with the Chicago Council on Global Affairs.

Early in the program, you heard from Patrick Ottman. He's with CNN. I'm Sean Ramos for him with Vox. Danielle Hewitt and Peter Balanon-Rosen made our show today. Amina Al-Assadi edited. Gabriel Donatab was on Fax. David Tadishore and Bridger Dunigan were on the mix for today Explained.