
Cuba seems willing to concede more than ever if the Trump administration is willing to take the win.
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Sean Ramisviram
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 gonna attend his large adult son's wedding.
Patrick Ottman
Person who I've known for a long
Sean Ramisviram
time, and he was like, probably not.
Patrick Ottman
He'd like me to go.
Sean Ramisviram
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 Castros took over in 1959. So we're gonna ask what could happen next on Today. Explained.
Cecile Shea
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Cecile Shea
Estares cuchando a hoy explicado today explained.
Sean Ramisviram
Patrick Ottman is CNN's Havana bureau chief.
Patrick Ottman
I am in Havana right now. Yes.
Sean Ramisviram
What's going on in Havana right now?
Patrick Ottman
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 cost about $300 to fill up my car.
Sean Ramisviram
Wow.
Patrick Ottman
You know, before you had really long lines at 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.
Sean Ramisviram
And on top of all of that, revolutionary Raul Castro was indicted by the United States a few days ago.
Patrick Ottman
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 US Many times during the Clinton administration, stop 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.
Sean Ramisviram
A third plane, flown by Brothers to
Cecile Shea
the Rescue founder Jose Basulto, managed to escape the attack.
Unidentified Guest
Smoke ball, perhaps even fire in it, to our north side of our aircraft, some perhaps seven miles away from where we were. And after that, there was complete silence from both aircraft.
Patrick Ottman
There was, you know, kind of no warning given. And these are planes that were unarmed. And that led to an increase in 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. 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 Alejandra, 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 US Administrations have kind of thought about indicting Raul Castro for this. And most of them thought, you know, too long ago, it is a sovereign state and they have the right to protect their country. It happened in international waters is what the US has always said. Today we are announcing an indictment charging Raul Castro and several others with conspiracy to kill US Nationals. Just. 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.
Sean Ramisviram
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 of.
Patrick Ottman
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 US Interests, that is responding when they make demands, and they would like something very similar for Cuba.
Unidentified Guest
The current model they have is it's not just them, 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.
Patrick Ottman
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 a change in leadership necessarily. The Castros could stay, but you open up your country. You need to allow Cuban Americans to come back and invest freely.
Unidentified Guest
Cuba's 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 isn't it impossible? Why is that not possible inside of Cuba?
Patrick Ottman
And you know, we need to see some, 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 ratcheting up pressure and the latest step in that has been indicting Raul 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 Ral Castro like we did with Nicolas Maduro. And if you don't think, you know, we can, you're in for a nasty surprise.
Sean Ramisviram
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.
Patrick Ottman
Raul Castro is 94. We saw him on Mayday, which of course has a lot of significance in Cuba. And you know, he looks exactly what you'd expect someone in 94 to look like. And so are you really going to send in the US Special forces that have to bring a wheelchair with them? I think, is it worth it? It's such an extreme policy in that you're obviously risking US 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 are open to make certain changes to their system without there 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.
Sean Ramisviram
One thing I wonder, comparing this situation in Cuba to the one in Venezuela that we've referenced a couple times, would Raul Castro in a Nike tracksuit just let the United States wheel him onto a plane and into MPD in Brooklyn? Or I mean, would this be like a cyanide situation?
Patrick Ottman
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 still alive. That was around when the Cuban revolution took place. And so they will put up resistance. I think Raul Castro probably 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. Cuz Nicolas Maduro was one of their closest allies. They see where he is now and they see this isn't just the US Saying this. To win Florida in an election every four years, 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, government with greater regularity than we've ever seen really before. And so there's just a tension. And certainly on the US 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
Cecile Shea
conveyed a message from President Trump. The US Is willing to work with Cuba on economic and security issues, but only if Cuba's communist government makes fundamentals changes. Ratcliffe putting pressure on Cuban officials to stabilize the country's economy and work with the Trump administration on security and economic issues.
Sean Ramisviram
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?
Patrick Ottman
People feel that it's really going to happen now? I think the fact that a president, a former president of theirs, whose name 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. There's, I've talked 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 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 cent country. 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 knock out the government here, then you're kind of just dealing with another failed state in the Caribbean like Haiti. And who picks up the 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. You know, 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.
Sean Ramisviram
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, Support for the show comes from Quince. Of course you might be looking to update your wardrobe not because you don't like the way you dress, but the fact that you want pieces that feel easy, comfortable and still put together. That's where Quints come in. Quince has all the wardrobe staples for spring. Think 100p European linen shorts and shirts from $34. Wow. That are lightweight, breathable and comfortable, but still look put together and clean. 100% Pima cotton tees with a softness that has to be felt. And Quince says that everything is priced 50 to 80% less than what you'd find at similar brands. Isn't that right Nisha?
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Unidentified Guest
Today.
Cecile Shea
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.
Sean Ramisviram
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?
Cecile Shea
I did watch it.
Sean Ramisviram
What'd he say?
Cecile Shea
He spoke Spanish, of course, he's a Cuban American. And he said, listen, Cuban people, people, it's not the United States fault that you don't have any energy, that your electricity grid is down. 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 lit. And it's time for you to pressure your government to step down.
Unidentified Guest
Lo unico que se interpone. El camino hacio mejor futuro son quiene controlan su pais.
Cecile Shea
That's a paraphrase, but that's generally what he said.
Sean Ramisviram
Is that generally true?
Cecile Shea
No, it is not generally true. There is truth to it in that yes, the government has, you know, 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 US Is forcing Venezuela not to ship oil to Cuba. Since US 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 that are affecting everything from homes to hospitals.
Patrick Ottman
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.
Cecile Shea
Now, for the last 50 years or so, the US has ensured that no country other than a couple that the US didn't hold 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.
Sean Ramisviram
What does make this moment different? Is it that this administration is willing to go further than previous ones?
Cecile Shea
What could be interesting about this moment is that Cuba seems ready to deal. Truth social.
Sean Ramisviram
No Republican has ever spoken to me
Patrick Ottman
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.
Cecile Shea
If we believe the press reports, and again, they're just press reports, but if we believe the press reports, Cuba has offered 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 and kidnapping 93 or 90, 94 year old men. And President Trump could finally be what he wants to be. He wants to do what every president since Eisenhower has wanted to do, which is end 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.
Patrick Ottman
I'd be hearing about Cuba.
Cecile Shea
So was Biden.
Patrick Ottman
Come on, man.
Cecile Shea
This is all very real personal history to them. And I do think that part of what 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 US and kind of move beyond revolutionary Cuba and some of the sloganeering.
Sean Ramisviram
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
Cecile Shea
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 that the trial would start. And he and his family are still heroes in Cuba, particularly with the older generation. So why mess with the Castros?
Sean Ramisviram
Can I offer.
Cecile Shea
Yeah, please do.
Sean Ramisviram
Is it what the diaspora wants?
Cecile Shea
So that's a good question. Or. 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 US and there's some evidence that among that million, million and a half or so emigres, they really are want to move forward. They're really not interested in fighting the wars of the 1960s anymore.
Sean Ramisviram
I think we've heard your best case scenario, Cecile, that the United States takes concessions from Cuba and allows the country on its own terms to transition to free elections that organically replaces the Castro regime. What's the worst case scenario here?
Cecile Shea
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 want. 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.
Sean Ramisviram
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 Venezuela nor 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?
Cecile Shea
Here's what I would say to some of those Americans. Imagine we could go two routes right now. Imagine we could start selling spare 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 harm's way 90 miles away from Florida, being 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.
Sean Ramisviram
That was Cecile 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 Ramisviram with vox. Danielle Hewitt and Peter Balin on Rosen made our show today. Amina Al Assad, he edited. Gabriel Donatov was on fax. David Tadashore and Bridger Dunnigan were on the mix for today, explained.
Cecile Shea
Sam.
Podcast: Today, Explained (Vox)
Hosts: Sean Rameswaram, Noel King
Guests: Patrick Ottman (CNN Havana Bureau Chief), Cecile Shea (Chicago Council on Global Affairs)
This episode investigates an unprecedented moment in US-Cuba relations following the Trump administration’s indictment of Raul Castro, the longtime Cuban leader and brother of Fidel. Amid historic power blackouts, economic collapse, and rising tensions, host Sean Rameswaram speaks to experts on the ground and in foreign policy about the logic and potential fallout of renewed American pressure—and even talk of regime change. The episode weighs the likelihood and consequences of US intervention, Cuba's economic crisis, the role of US policy (sanctions and embargoes), and what the future might hold for the Cuban people.
Guest: Patrick Ottman, CNN Havana Bureau Chief
Segment: [02:22]–[05:59]
Guests: Patrick Ottman, Sean Rameswaram
Segment: [03:00]–[08:06]
Guests: Sean Rameswaram, Patrick Ottman
Segment: [08:06]–[13:22]
Guests: Cecile Shea, Patrick Ottman, Sean Rameswaram
Segment: [17:29]–[20:00]
Guests: Cecile Shea, Patrick Ottman, Sean Rameswaram
Segment: [20:00]–[24:09]
Segment: [24:54]–[27:06]
This episode underscores a pivotal and dangerous juncture: renewed US pressure on Cuba (including unprecedented legal and military threats) amidst deep Cuban suffering and diplomatic openings from Havana. Experts argue that the real causes of Cuba’s crisis are more complex—and American choices could mark the difference between prolonged suffering, pointless intervention, or a long-awaited peaceful transition.
For full context, listen to the episode. All quotes are direct from the respective speakers.