Why Trump wants to ‘take’ Cuba

As the war with Iran becomes more entrenched, President Donald Trump now says he thinks he’ll “have the honor of taking Cuba.” What does that mean and what’s at stake?

Patrick Oppmann, Havana bureau chief for CNN.

Michael Bustamante, associate professor of history and chair of Cuban Studies at the University of Miami.

Ricardo Zúniga, founding partner of Dinámica Americas, a strategic advisory firm focused on Latin America, North America and the Caribbean.

The version of our broadcast available at the top of this page and via podcast apps is a condensed version of the full show. You can listen to the full, unedited broadcast here:

Part I       

MEGHNA CHAKRABARTI: President Donald Trump's hegemonic thirst continues unabated. The list so far. Greenland. At the end of 2025 and the beginning of this year, Trump said he would take Greenland, quote: One way or the other. And that it would happen, quote: Whether they like it or not. He dismissed Danish control of Greenland, but the Danes did not dismiss Trump's invasion threat.

In fact, just today, Danish public media, DR, reports that in mid-January, Danish military forces were deployed to Greenland, including with blood transfusion supplies and explosives. A military source tells DR, quote: There was no possible ambiguity. End quote.

To both the Danish deployment and the reason why, DR reports that the troops were sent to protect Greenland immediately after Trump's January 3rd military operation in Venezuela that captured former President Nicholas Maduro. Quote: When Trump says all the time that he wants Greenland, and then we see what happens in Venezuela, we had to take all possible scenarios seriously. End quote.

That's from DR's military source. In fact, also today, Danish Prime Minister Mette Frederiksen said concern is still high in Denmark.

The Prime Minister says:

"Unfortunately, I still believe that the American President's desire to take over Greenland is intact, and therefore this situation is serious, and it has been so all along."

CHAKRABARTI: Again, that was just today in Denmark. Then of course there's Venezuela. As mentioned, Trump ordered a unilateral attack on Caracas that led to the successful capture of former President Nicolás Maduro in early January.

Maduro currently awaits trial in New York. Venezuela's current leader, Delcy Rodríguez, was Maduro's vice president. Her politics aren't all that different from Maduro, meaning very little has changed for the Venezuelan people. Rodriguez, however, is willing to cooperate with Trump. And then of course, for the past three weeks, Iran.

The U.S.-Israel war with Iran is spiraling out of Trump's control.

Just yesterday, Israel bombed the South Pars gas field, a significant escalation in the war. Iran immediately retaliated attacking Ras Laffan Industrial City. Trump claimed that the U.S. knew nothing about Israel's bombing plan, but military sources tell a variety of U.S. news outlets that Trump did know.

And approved of the bombing. On Truth Social, the President flailed. Last night in one post, he acknowledged the danger of attacking one of the world's largest natural gas fields. Then he also lashed out at Israel, writing in all caps, no more attacks will be made by Israel. End quote. Then in that same post, he lashed out at Iran saying that if it continued its retaliatory attacks on Qatar, the U.S. would, quote, massively blow up the entirety of the South Pars gas field at an amount of strength and power that Iran has never seen or witnessed before.

End quote. Now I am going through all of this because it's the backdrop for today's show. Because none of the above has quenched the president's thirst for domination. Just this week on Monday, he said:

I do believe I'll be the honor of having the honor of taking Cuba. That'd be good honor. That's a big honor.

REPORTER: Taking Cuba.

Taking Cuba in some form. Yeah, taking Cuba, whether I free it. Take it. I think I could do anything I want with it. You want to know the truth? They're a very weakened nation.

CHAKRABARTI: is Trump speaking to reporters at the White House on Monday and here he is, just a day later, Tuesday.

TRUMP: Cuba right now is in very bad shape. They're talking to Marco and we'll be doing something with Cuba very soon.

CHAKRABARTI: Marco there, the president's referring to, of course, Secretary of State, Marco Rubio, who also weighed in on Tuesday.

MARCO RUBIO: The bottom line is their economy doesn't work. It's a non-functional economy.

It's an economy that has survived. For 40, that revolution. It's not even a revolution. That thing they have has survived on subsidies from the Soviet Union and now from Venezuela. They don't get subsidies anymore, so they're in a lot of trouble and the people in charge, they don't know how to fix it, and so they have to get new people in charge.

CHAKRABARTI: In fact, Cuba and the United States have actually been in talks for at least the past couple of weeks, and that's because approximately three months ago, the U.S. effectively imposed an oil blockade on Cuba, amongst other things. Now after those most recent comments from the Trump administration, the current president of Cuba, Miguel Díaz-Canel, fired back.

He wrote on X, quote: The U.S. publicly threatens Cuba almost daily with the forceful overthrow of its constitutional order. Cuba has one guarantee. Any external aggressor will encounter an unbreakable resistance. End quote.

So let's get a deeper understanding of the White House's aims with Cuba. And we're going to start today in Havana.

Patrick Oppmann joins us. He's CNN's Havana Bureau Chief. Patrick, welcome.

PATRICK OPPMANN: Thank you so much.

CHAKRABARTI: Can you just first of all tell us what daily conditions are like in Cuba? Just a few days ago, in fact, the entire island lost its electricity supply. Yes?

OPPMANN: Absolutely. And power at my house was off this morning.

We have power at the office where I am, our Havana Bureau. But apologies ahead of time if for some reason I just disappear. Because the power goes off here, I don't think it'll happen. But it could and that's our day-to-day life, is juggling the daily outages which could become much longer outages, and we've seen over the last few weeks have gone from being hours to sometimes lasting days.

CHAKRABARTI: Okay. And is the power outage then directly related to the U.S.' oil blockade on Cuba?

OPPMANN: Yes, because while the power system here has been shaky for years and blackouts are just a normal part of life in Cuba, we've never seen them like this before. Cuba's grid runs off oil. The oil needs to come from countries like Venezuela, Mexico, Russia, and now with the oil blockade, we haven't received any oil according to Cuban officials, for three months.

And so right now, to fill up my car, if I can find gasoline, I'd have to buy it from someone who has it. They're charging about $300 a tank at the moment, which is more than a Cuban makes in an entire year on a state salary. And you don't see cars on the road.

If I can find gasoline ...they're charging about $300 a tank at the moment. Which is more than a Cuban makes in an entire year on a state salary.

Patrick Oppmann

Power outages are lasting longer and longer. It's a good day if you get anywhere from four to six hours, and this is impacting every aspect of life here.

CHAKRABARTI: So energy is the fundamental thing we need for delivery of food, for pumps, for water, et cetera. Are those things also now under threat in Cuba?

OPPMANN: Yes. And in a lot of ways, not having water is worse than not having power. And you correctly point out that the pumps for water, because you don't get water here every day, you have an allotment of water. The system for delivering water here, again, is also broken down and antiquated.

But if there's no power than your day of water, as they call it here, doesn't happen. And you're left without water. So people are stockpiling water, they're stockpiling everything. And of course, when you don't have powerful longer than a day, your food begins to spoil. And that's really the hardest thing for Cubans, because food is so expensive compared to what they earn.

It takes such a huge effort to feed yourself and your family. And when the food begins to spoil, that's when we've seen people go out in the street and start protesting against their government. Just out of frustration.

CHAKRABARTI: Okay. So I want to talk to you about that in just a second, Patrick. But first we have a little bit of tape of Cubans themselves.

This is Havana resident ... who told the German public broadcaster DW that she's trying to live her life in the dark.

She says: We can't do anything. I eat in the dark. I sleep in the dark. I have breakfast in the dark, I shower in the dark. Always everything in the dark all night. What else can I say?

CHAKRABARTI: And here's another one. This is a Cuban woman who was interviewed by Reuters. She didn't give her name to Reuters, but she also said she's losing patience with the difficulties her country is facing.

CUBAN WOMAN: We're collapsed. We can't stand this situation anymore. I think that if this conversation between Cuba and the United States is to find a better solution and to have a better prepared Cuba with more chances to move forward in this country because we can't stand it anymore.

CHAKRABARTI: That's a Cuban woman who spoke with Reuters.

Patrick, one more question, first of all about life on the ground. Just quickly, are things like health care being disrupted, education, other aspects of Cuban life?

OPPMANN: Absolutely. You go to any hospital now and the power will be off. There are something like 100,000 people on a list, a waiting list for surgeries.

Most schools, of course, don't have generators either. And if you have a generator, you need fuel to operate it. So, you know, people when they get power, sometimes it's in the middle of the night and they rush around to do their cooking, their laundry, charge, their devices. Because they don't know how long the power will be on.

It really has a psychological impact when you, day to day, don't know when the power's going to be on, how long it'll be on for, and it could just go off and not come back at all.

It really has a psychological impact when you ... don't know when the power's going to be on.

PATRICK OPPMANN

CHAKRABARTI: How are people getting through day to day then? What have you seen? Yeah.

OPPMANN: You see an exhaustion in people's faces. You see an incredible worry.

It feels, people talk about it being tiempos de guerra, times of war without a war. And an oil blockade is essentially a wartime maneuver. And so the Trump administration, they know time is on their side. The longer this goes on, the worse it will get for regular Cubans.

CHAKRABARTI: Now, the United States, of course, has basically had an economic blockade on Cuba for, what, 40 plus years.

So this is just adding to that already fragile economic state that the island has experienced. You had said a little bit earlier that we're starting to see protests on the streets of Cuba against the Cuban government. Elaborate.

OPPMANN: So people get frustrated and what has happened is time and time again, is if you go out and protest, then they take away power from a different neighborhood and give you power to get people to go back inside.

Protesting is not allowed here really in any form or manner. It's still a single party, communist state, and in times past when people have gone out and protested against the government has come in and cracked down very hard. This is also part of the U.S. policy towards Cuba.

We've seen throughout the years, where documents are declassified and the whole point of having an embargo, in many ways is not to change just the behavior of the Cuban government, because that has not changed. It's to make people unhappy enough that they try to tear down this government.

So what we have seen is people frustrated at the poor way the government is managing this crisis, going out, beating pots and pans, and essentially calling for the power to be turned back on. But also, it's taken a political edge where in one town, people try to burn down the headquarters of the Communist Party.

For the people who have felt discontent really over their whole lives, the government looks weaker than it ever has before.

CHAKRABARTI: We just have a few seconds before the break, Patrick. And how are they looking at the Trump administration?

OPPMANN: Some people, you look at it through the prism of Cuban politics, and so if you don't like the government, you support what the Trump administration is doing.

Other people, Cubans are very proud and love their country, if not their government, and they don't like this idea of the U.S. trying to take over their country.

Part II

CHAKRABARTI: Today we're talking about Cuba and specifically the Trump administration's designs on Cuba. Just this week, the president said it would be an honor to take Cuba. I'd like to introduce Michael Bustamante into the conversation now. He's in Miami.

He's an associate professor of history and chair of Cuban Studies at the University of Miami. Professor Bustamante, welcome to On Point.

MICHAEL BUSTAMANTE: Thanks for having me.

CHAKRABARTI: And I'd also like to introduce Ricardo Zúniga. He's the founding partner of Dinámica Americas, s a strategic advisory firm focused on Latin America, North America and the Caribbean.

He also served for 30 years in the U.S. Senior Foreign Service, and in the Obama administration, he was on the team that held secret negotiations with the Cuban government that resulted in diplomatic and economic openings back then.

Ricardo Zúniga, welcome to On Point.

RICARDO ZÚNIGA: Thank you.

CHAKRABARTI: Okay, so let me ask you both, first and foremost, what do you think, what can we discern about what Trump's end goal is with Cuba right now?

Professor Bustamante, let me start with you.

BUSTAMANTE: It's been really hard to tell. The rhetoric honestly has been a little bit all over the place. Particularly against the backdrop of reporting that suggests that some talks are going on between both governments. In fact, I think that much has been confirmed, and the Trump administration has also acknowledged that.

So how one square is the kind of off the cuff comment that the president is interested in taking Cuba with reporting of ongoing talks with elements of the Cuban government for some kind of negotiated exit that would presumably leave part of the Cuban government in power if the Trump administration gets its way.

That's been a very difficult thing to try to figure out.

CHAKRABARTI: Ricardo Zúniga, your thoughts?

ZÚNIGA: No, I agree. Look President Trump is going to define winning as whatever he decides winning looks like. And that could be very different from historical U.S. aims in Cuba, which were to promote a democratic change and an open economy and end the authoritarian government there.

But again, as we saw in Venezuela, this is an administration that is quite comfortable breaking with longstanding norms, even when it means leaving an authoritarian regime in place, as it did in Venezuela. It's possible you could see that same end state in Cuba, which would be very surprising to people who voted for the president in South Florida.

CHAKRABARTI: But Ricardo, let me just press this point a little bit because it does feel as if right now, I take both of your points about how the president speaking off the cuff is one thing. It's hard to discern what his true goals are. But at the same time, we have, as I said a little earlier, of course, the Venezuela example of he eventually, he did take action there and depose the sitting government or the sitting president.

And then also we have not just President Trump, but in the form of the Secretary of State, Secretary Rubio. We have a family member of Cuban exiles who's long been a very strong voice against the communist government in Cuba, and I just wonder if these things coming together makes you wonder if the U.S. would actually move so far as to take military action, Ricardo?

ZÚNIGA: I very much doubt that they would take military action in the case of Cuba. For one thing, the U.S. is fully occupied with Iran. And this is not like the operation in Venezuela. Cuba and Venezuela are very different cases. And there wouldn't, there's no single person, no single Cuban that they could remove from power that would make the rest of the government more malleable.

I very much doubt that they would take military action in the case of Cuba. For one thing, the U.S. is fully occupied with Iran.

Ricardo Zúniga

It's a much more cohesive government than was the case in Venezuela. So Venezuela's really the wrong model. If that's what they're looking at.

CHAKRABARTI: No. So tell me more. Tell me more. Go ahead.

ZÚNIGA: So the reality is that Cuba has fewer resources than Venezuela. It is in a much more dire state. And I think the other reason why military action isn't likely is because it's obvious to everyone except maybe the very top tier of the Cuban leadership, that this model is done.

And they need to, change is necessary and there's enormous public pressure for change from the island, notwithstanding the U.S. position on this. They are done. Effectively, I think Secretary Rubio was right. The end of subsidies really means the end of this model.

So there's no real need for military action either to exert leverage.

CHAKRABARTI: Okay. So I want to come back to that in a second. But Professor Bustamante, just your thoughts on whether Venezuela is the right or wrong model to be considering here.

BUSTAMANTE: I think it's interesting that administration officials themselves have been citing the Venezuelan model as something that they want to follow in some way.

U.S. officials have been going around and saying in private conversations and in some public comments that part of what they're doing is trying to marry this external, this extraordinary external pressure with a search for a quote-unquote Cuban Delcy Rodríguez. But I agree with Ricardo, it's not clear who that person would be.

There's not really a person in the Cuban government that stands out right now with minimally reformist credentials. And the Cuban system is a much more, in a way, cohesive ideological system than the Venezuelan system ever was. So I think the recipe doesn't quite make exact sense here, which I think is partly why the administration may be leaning towards some kind of negotiated exit and trying to get as much as they can out of that, using the leverage that they have.

CHAKRABARTI: Okay. But let me ask both of you this, I do to your point that in terms of like practically speaking, there may be nothing that the U.S. gets out of even trying to change the government in Cuba, but it's never really been about practicality, right? Save the Soviet Union's influence historically in Cuba, it's been about politics exclusively. So is that not seen as a potential major gain if Secretary Rubio or President Trump could say, we finally, after 40 years of ineptitude, I presume the president would say, of other occupants of the White House, we finally freed the Cuban people.

As we've seen with the president thus far, it takes very little motivation or very little reasoning for him to actually make decisions that are quite consequential. Professor, what do you think?

BUSTAMANTE: I agree and you raise a good point. So even though the logic would not favor something like military action I think the Cuba thing for this administration is as much about symbolism as anything else.

Cuba does not have vast reserves of oil, so the kind of economic interest calculation is not the same. But to be able to say and plant the flag that we are the administration that did this thing that no other administration had done before, that's certainly something that would appeal to the president's I think own sense of self-importance. I can imagine the Secretary of State selling this to him on those terms, but again, how you get from point A to point B is a very different story. And I think that's where the rubber meets the road, particularly given everything else that's going on.

But I agree. I don't think you can rule out extreme scenarios.

Let's envision a repeat of mass protests like those that occurred in 2021 in Cuba. If that happens, is this administration in this moment just going to stand back with their arms crossed? I think that's difficult to imagine.

CHAKRABARTI: Okay. Ricardo Zúniga, let me ask you, does it make any sense right now, okay.

Given everything, all the other conflicts that the president has gotten the United States enmeshed in, obviously Iran being No. 1 on that list at the moment. For the U.S. to continue to put this kind of pressure on Cuba, we don't even know who the talks are, who's doing the talks on behalf of the United States.

Do we?

ZÚNIGA: No we don't. And that's fine if you're, I think that for sensitive conversations like this, it's better that they be secret, frankly, so that you, if you really intend to make progress. But the challenge is this, I think that Michael is right. There's no sort of single reformer or individual who can, who stands out and who could be the Cuban Delcey, which is what I keep, I have also been hearing the same thing from U.S. officials. That's not likely to happen.

They're going to have to bring along a group of people who aren't sure at all about what future, what the future holds for them. And so how do you achieve that political aim, that longstanding political aim so you can claim victory without kind of defining what the future looks like for the people who hold all the guns and the power in Cuba right now.

And so that's, like how do you get exactly right, getting from point A to point B is the real challenge now, and there's a lot that needs to be done in Cuba. And we shouldn't forget that there's the very real situation of the condition of the Cuban people, which Patrick was describing. And people are dying now because of the blockade on the oil.

CHAKRABARTI: Yeah. Yeah. Everything that both of you're saying makes perfect sense in a normal political world. But what we see right now is a president of the United States who's entirely unburdened by the need to define what success looks like. Because he changes the definition on a daily basis. So let's just imagine for a moment that this actually is a pivotal time for the United States to affect some kind of political change in Cuba.

What I'm hearing from both of you, though, is that we don't know if that would be successful at all. Could it potentially, could the United States involvement right now potentially leave the Cuban people, specifically, Ricardo, in a worse place?

ZÚNIGA: Oh, absolutely. Look, that's the case today. And so I think it is true that many Cubans want change, any change, but they don't want the invasion of Cuba.

I don't think they want to suffer more. What they want to see, they just want normal lives. And they want the same things that people in the United States want and in their daily lives and that they haven't seen for years and conditions that have gotten worse and worse. So yes, absolutely, U.S. military action coupled with what's already happening in the economy and the shutoff of energy sources is potentially a recipe for a humanitarian disaster on the island.

CHAKRABARTI: Let's listen to a little bit. We keep talking about these talks that we actually don't know much about, but let's listen to Cuban President Miguel Díaz-Canel on Friday of last week, acknowledging that the U.S. and Cuba are in fact in talks.

But he says they are in the early stages.

"These are processes that are done with much discretion. They are long processes that have to first be initiated by establishing contacts, that there are opportunities for dialogue and a willingness to engage in dialogue. And all of this takes time. And based on that, agendas are being developed, negotiations will begin, talks begin and agreements are reached.

Things we're still far from since we're in the early stages of that process."

CHAKRABARTI: End quote. Professor Bustamante, do you want to try to glean any intel from what the Cuban president is saying there?

BUSTAMANTE: Sure, I'll do my best. I think this was the worst kept secret. This has been, the talks have been reported on for a number of weeks, and the fact that it made news that the president of Cuba was acknowledging something that everyone else seemed to know was I think a testament to how slow change happens in Cuba.

The other thing that I would note about his announcement, he made a point of indicating that these conversations, whatever they are, were being conducted at the direction of the historic leader of the revolution, Raúl Castro, who's technically retired and not the head of state. But also insisted that he had also been involved. And emphasized that.

And I think that is a direct response to the reporting and suggestion that this is, these talks are proceeding without his involvement and that he's a kind of a lame duck person who doesn't have much of a say in really shaping the leadership agenda. I think time will tell where that goes.

The only other thing I would note is that, to me, Díaz-Canel's rhetoric did not seem to quite reflect the urgency of the moment. Either for his government or the people. The notion at another point, he said, the talks are just getting started and we're at the stage of defining what the issues are that need resolution, as if we don't know from 60 plus years of what the issues are in U.S.-Cuban relationships.

So I think Cuban people might have liked to hear more urgency from their leader as to how seriously they're taking this.

CHAKRABARTI: Ricardo Zúniga, I'd love to mine your experience as being a U.S. negotiator or on the team of U.S. negotiators with Cuba in the Obama administration. What was it like negotiating with Cubans then?

Who did you talk to? How did that go? And then later on I'm going to ask you about what would you talk about, talk with them now if you were on the negotiating team, but give us a little bit of your historical experience.

ZÚNIGA: So the history of U.S.-Cuba talks is mostly a history of talking past each other.

And certainly, there was a lot of that in the negotiations that we undertook on behalf of President Obama. We did, unlike the current administration, we did keep our talks secret throughout, because that was the only way that either side could have the political space to negotiate hard things around the relationship. And they were hard, difficult conversations.

We simply have a very different worldview, a different vision of history. And as I remember going in, that number one I was struck by the fact that the people that we were talking to on the other side, one of them was Alejandro Castro, son of Raúl Castro, but the rest of the team had been negotiating with the United States for at least 15 years.

In other words, they bring a lot of expertise to these conversations. That's their pattern. And they will be doing the same thing in the conversations with the Trump administration for certain. They'll bring in people very experienced in the U.S. relationship.

The conversations are hard, because what the United States seeks really gets at the heart of the authoritarian government in place in Cuba today. And if we seek greater freedoms, at least that traditionally has been what the United States has been pushing for. That goes directly contrary to the Cuban government's view of itself and its interest in remaining in power indefinitely.

You know, we're talking about pretty serious differences. At the same time, we could make progress on pragmatic issues, which is the terrain that the Cuban government favors. If it doesn't imply regime change, then they are willing to talk about quite an array of issues.

We're neighbors. And so there are many issues that come up with Cuba that are fairly mundane, have to do with the safety and security of our citizens. But on the fundamental issues, human rights, the geopolitical alignment and so forth, those are areas where we historically have just not been able to make much progress.

And I think in our case, in President Obama's case, he wanted to put to bed this longstanding relic of the Cold War.

CHAKRABARTI: Ricardo, if I may, I have to say, I love how diplomats talk sometimes because they insert clauses in the middle of their sentences that are quite consequential, but you might not notice them.

And one of them that you did just now was that historically the United States has wanted to introduce some more freedoms in in Cuba. And you said, at least traditionally, that has been the case. Meaning you don't feel that's necessarily the case now with the Trump administration.

ZÚNIGA: I think that's not the case. So I think, here's one thing that I'm sure that they all want. The reason that you're hearing about the removal of the President of Cuba, who is honestly not a particularly consequential figure in Cuban history, he is one of a consortium of leaders.

But symbolically removing him then gives the Trump administration a plausible position that they have changed the government of Cuba, and then whoever comes next, if they do what they did in Venezuela, and draw from the current leadership ranks. It is going to have to be somebody with a strong background in the Communist Party or the armed forces of Cuba. And I think that for, at least for the president, is not interested in democracy.

He certainly has made no allusions to that in Venezuela or in other conflicts. Whereas Secretary Rubio is going to probably have a very different set of interests, coming from South Florida where the removal of the entire communist apparatus is really the goal.

Part III

CHAKRABARTI: Today we are talking about what the Trump administration, what President Trump has been saying about his designs on Cuba. For example, on March 9th at a news conference in Doral, Florida, a reporter asked President Trump what the US would get out of a deal with Cuba.

And here's Trump's answer.

TRUMP: It may be a friendly takeover. It may not be a friendly takeover. It wouldn't matter. Because they're really in, they're down to, as they say, fumes, they have no energy, they have no money. They're in deep trouble on a humanitarian basis. And we don't want to see that. But they were very bad to a lot of people, and a lot of people living, the Cuban American vote, which I got at record levels, very important to those people are very important to me.

I know what they went through. They went through hell. Some of them have gone on to be some of the most successful people in the country. Cuban American businesspeople, some of them are like the most successful in the country. And a lot of them are friends of mine, because I've been fighting this battle with them for a long time.

The Castro regime was brutal.

CHAKRABARTI: That's the president on March 9th. Ricardo, can I just ask you a quick question? Do you know what the president is talking about when he says he's been fighting this battle with them for a long time? I can't quite suss that out.

ZÚNIGA: Yeah, no I can't either.

So I don't know. It's hard to again parse out what he means by that. There's been, Cuba has not been especially important to him. As a Venezuela by comparison has been much more important.

CHAKRABARTI: Okay. Here's another statement from Trump. This is from March 15th, so six days later aboard Air Force One.

And again, he was asked, what does he want from Cuba in these ongoing talks? And here's the president.

TRUMP: Cuba is a failed nation. Cuba also wants to make a deal, and I think we will pretty soon either make a deal or do whatever we have to do. We have a lot of great people that happen to vote for Trump.

Not that that matters, but we have a lot of great people from Cuba that were violently and viciously thrown out of the country. And worse. Their families were killed, and so we are talking to Cuba, but we're gonna do Iran before Cuba.

CHAKRABARTI: Of course Air Force one being quite loud, the president there saying in part Cuba also wants to make a deal.

He says he thinks they'll get there pretty soon. Didn't offer any evidence or reasoning behind that. But that's his assertion. And then he rounds off that statement with saying, quote, and so we are talking to Cuba. We're going to do Iran before Cuba.

Okay. Gentlemen, I'd actually just like to take a quick step back here. Because we have to talk about the role that history plays with any U.S. interaction with Cuba.

It's been, what, more than six decades that Cuba occupies this unique place, I would say, in the American political psychology as the next-door neighbor that still stands as an eternal reminder of the former Soviet Union and the existential threat of the Cold War. Ricardo, since you have been a U.S. diplomat in this world, how does that history play into this moment?

ZÚNIGA: On the Cuban side, I assure you this feels like a part of the continued arc of its relationship with the United States. They, the people who are in charge of Cuba now, some of them were founding members of the Revolution. So for them, this has been their entire existence.

As leaders, as people in government. For the United States, Cuba became less and less relevant as a security matter. And became more and more of a symbolic instance of a country that stood in opposition to the United States and allied with us adversaries all the way through till now.

They used to, Cuba used to be much more influential in the Americas. That has diminished dramatically over the last 15 years in particular. But if you're a U.S. diplomat, Cuba was always the adversary that was on the other side of almost every issue that mattered in Latin America.

CHAKRABARTI: Professor Bustamante, did you want to add to that?

BUSTAMANTE: Yeah, sure. The relationship between Cuba and the United States has had certain sized importance. And I think the imaginary of both countries since long before the Cuban Revolution, in fact, I think the Cuban Revolution comes out of this long and torturous relationship, these ties of singular intimacy, as President McKinley called them.

And I think the shadow of that longer history is upon us. When the president sort of talks off the cuff about a takeover of Cuba and Cuban audiences hear that, and might rightly think about 1898, when the United States intervened in Cuba's War for Independence and occupied the island for four years and helped birth the Cuban Republic, but under a tremendous U.S. shadow.

And 50 years later, you get a Cuban revolution that in some sense is the product of the grievances that are born out of that initial starting point. So the histories are long and deep. They're felt very keenly on the Cuban side. Ricardo's absolutely right. I remember very well when President Obama traveled to Cuba for a historic visit in the spring of 2016, and gave a nationally televised address. And part of the thread of that speech was about the need to bury, not bury, but put history to bed and look forward. And that generated such a strong counter reaction from the Cuban state.

The irony though is that if this history still continues to matter so much for Cuban officials and an official narrative, for Cuban citizens, particularly the two generations that have come up since the fall of the Soviet Union, who know nothing but one degree or another of crisis, they often don't have as deep an understanding of this history.

And they are really looking to just move forward and put it behind them. Which I think has left them open to a kind of dramatic action from the United States potentially in ways that they might never have been before.

CHAKRABARTI: Okay. But Ricardo Zúniga, as you were saying earlier, it's not the Cuban people who are at the negotiating table right now, nor have they ever been, and so let's be like, let's be as unflinchingly realistic as we possibly can.

Because I'm thinking back to the negotiations that you were part of in the Obama administration, and they did bring some successes regarding diplomatic relations and economic openings between the United States and Cuba. But I don't imagine that political change was ever on the table, if indeed to this day Cuba's, as you were saying, that history that we were talking about still weighs so heavily in the minds of Cuban leadership. It seems entirely unrealistic to think that any negotiation, current or the ongoing negotiation, would, that the Cubans would be open to introducing substantial political change on the island.

ZÚNIGA: Right, absolutely true. And so during our negotiations with the Cubans, which were a lot less coercive than the ones that we're seeing now between the Trump administration and Cuba, that was a different time. Cuba still had more resources than it does now. It was a better condition overall.

Now they have very few choices, much more limited, much more limited public support. Because they, the population, as Michael said, has lived through these cycles of rising expectations and then only to have their hopes dashed. So I think that frankly, the Cuban state is becoming less and less relevant. Like the U.S. notwithstanding, the private sector in Cuba, small, formal and informal is becoming more and more important and a greater factor in people's lives.

And the state simply cannot provide what it could before. And the subsidies are done, the external subsidies are over. The model's dead and it has been for some time. But now reality, that's their harsh reality, that they may not want to see any kind of change or envision a future for Cuba without them in charge.

But those circumstances are starting to come out of their hands at this point.

CHAKRABARTI: I'm sorry, I'm just pausing here. Because again, practically speaking, I think everything that you're saying is making sense, but then why isn't the U.S. stepping back and just letting that slow crumbling happen? Is it frankly because we have the son of Cuban exiles as Secretary of State right now, I just don't really understand what advantage the U.S. thinks it has at this moment.

ZÚNIGA: I think Michael put it well, our countries live very large in each other's minds. And so I think it's impossible for the United States. It is our neighbor, so there is that. So the question of whether it makes sense for us to assist in the destruction of the society of a neighbor living right next door to us.

That's a very good question to ask, but I think it's impossible to imagine the United States not doing anything, regardless of who is in the White House at a moment like this, but you're exactly right. So the question here is, how do you stimulate change, positive change in Cuba?

With a government that it feels like its very existence, a physical existence as people, is on the table. That's the situation for them.

CHAKRABARTI: I'm going to come back to that in a second, but Professor Bustamonte, let me ask you this, because we've been talking exclusively about U.S. and the United States and Cuba, but I'm wondering, the Russians have said, I think there's been some reporting that the Russians have said they're going to continue to support Cuba.

There are subsidies and maybe plus some, I don't know if China's playing a role here. How do you read all that?

BUSTAMANTE: Yeah. Russia and China have absolutely been key allies, trade partners of Cuba in recent memory. The reporting this morning is that there's a couple of ships from Russia with oil on their way to Cuba that will represent, one of the first challenges to the ostensible oil blockade.

And perhaps they're seeing an opening given everything that the United States is focused on in the Middle East. But I think it's also important to note that while the rhetoric from the Russian and Chinese governments is one of solidarity, one of opposition to what the Cuban, the United States government is doing to Cuba, neither of these countries is willing to bail out the Cuban economic model.

They themselves have said to the Cubans on friendly terms or somewhat less friendly terms, you guys need to change. The Russians even proposed a kind of a massive plan for restructuring the Cuban economy a couple years ago that went nowhere. So everyone's frustrated. Fidel Castro himself, I think 15 years ago in an interview with, I think it was The Atlantic's Jeffrey Goldberg said the joke, the model doesn't even work for us anymore.

And so the last decade has been this cycle of missed opportunities for reform. And there's no one to bail them out. And I think for that reason, going back to your prior question about what the United States is actually after here, given what they did in Venezuela, they sense that they have leverage and they do in theory.

The question here is time and political will on the Cuban side. Can the Trump administration use that oil leverage to prod the Cuban government to concede on things they've never conceded on before, while the Cuban people are suffering in the middle? Or will the Cuban government try to run out the clock? And so that's what worries me the most, the sort of differential timelines on which the diplomatic process may play out, versus just how quickly the humanitarian situation is deteriorating on the ground. And that is not a good recipe for rebuilding a society in any form.

CHAKRABARTI: Michael Bustamante is the associate professor of history and Chair of Cuban Studies at the University of Miami. Professor Bustamante, thank you so much for joining us.

BUSTAMANTE: Thank you.

CHAKRABARTI: Ricardo Zúniga. I hope you forgive me for just making this very kind of rudimentary observation, we've been talking about the Cuban people here through the whole hour and I just want to underscore that they are suffering even more right now. That the Trump administration has made the decision with ... essentially, its effective oil blockade to increase the suffering of the Cuban people with the hopes of creating some kind of political leverage. That's a choice made by Washington on the innocent people of Cuba.

ZÚNIGA: Yes, it absolutely is. And the whole premise of President Obama's approach to the issue was that the conflict was going to continue between the two governments, but we should do what we can to alleviate the suffering of the Cuban people and let them solve some of their own problems.

Encourage agency on their behalf. Let them make their lives as good as they can while the governments continue their dispute. This is the opposite. This is essentially using the pressure cooker of the destruction of Cuban society to try to generate a revolution from below.

That's the objective. And, but of course, it becomes a much more unmanageable situation quite apart from the humanitarian concerns. Having a violent overthrow of a government always has unforeseen consequences.

CHAKRABARTI: Let me ask you, from your experience, your long experience with Cuba, specifically, that pressure cooker to create a revolution from below, do you think that there's any possibility that could happen?

Given the current circumstances. Yeah, go ahead.

ZÚNIGA: Look, Michael had it right that under the current circumstances we have not seen before. And so you can't predict based on what's happened in the past. You certainly have had large demonstrations. The Cuban state remains very capable in terms of its repressive capacity, no question there.

So it would be difficult for ... to see this kind of change go forward unless parts of the state itself defected in favor of change, in support of change, members of the armed forces, or the security forces or members, other members of the state. And we don't see that right now. What we see right now is that as unhappy, as angry as the population is, as much as they desire change, nobody wants to be the last victim of this government.

So to an extent, it's still easier to try to leave Cuba rather than try to force change. And that's been part of the logic of repression in Cuba. Give people an out, a safety valve that's been migration in the past, but this is a very different circumstance. So yes, it's plausible to imagine some kind of uprising in Cuba, and again, people are quite desperate. They just want normality. They want power but they want to see some kind of trajectory of hope. And that's non-existent right now.

CHAKRABARTI: Now, Secretary Rubio has said that Cuba does not have to change from one day to the next. He says everyone is mature and realistic.

That's a quote from him. It doesn't need to change all at once. Ricardo, in the last 30 seconds we have, then ideally, what change, if any, would you like, would you hope to see in the coming, weeks, months, years in Cuba?

ZÚNIGA: I think in the short term, we would want to see improved social and economic conditions, so that would mean removing pressure on the private sector and allowing much more freedom.

Of people to, again, solve their own problems. So that would be crucial. You would want the release of all political prisoners and commitment by the state to begin easing the kind of the pressure that they've put on the political side of the equation as well. And a gradual but very evident move towards opening up Cuban society.

That's what we need to see. And how you get there, again, is a matter of debate. But it's necessary for us to see a successful neighbor in Cuba.

The first draft of this transcript was created by Descript, an AI transcription tool. An On Point producer then thoroughly reviewed, corrected, and reformatted the transcript before publication. The use of this AI tool creates the capacity to provide these transcripts.