Cuba’s Future and U.S. Interests

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Cuba is at a strategic crossroads as the near collapse of its national energy system reshapes the island’s political landscape. Intense U.S. sanctions and the loss of energy support from traditional partners like Venezuela have left the Cuban government in its most vulnerable state in decades. While Havana seeks diplomatic paths forward, the current U.S. administration sees an opportunity for changing a government that Washington has declared “an unusual and extraordinary security threat.” This crisis moment carries profound implications for U.S. foreign policy and for broader geopolitics.. What is the current situation in Cuba, and how is Washington’s geopolitical pressure impacting its governance? What role might other countries, like Russia, play in this situation? And what are most likely future scenarios for Cuba?

Join us for an insightful discussion that explores the current state of affairs in Cuba and its future trajectory. Our speaker for this briefing will be Emily Mendrala, former Deputy Assistant Secretary of State in the Bureau of Western Hemisphere Affairs.

Music by Sergii Pavkin from Pixabay.

Transcript

SPEAKER_04 0:00

Over the past month, Cuba's electrical grid has gone down repeatedly. Sometimes, for days at a time. Schools are closed, hospitals have canceled surgeries. An estimated three million people have left the island in the last five years. Then in January, after removing Maduro from Venezuela, the U.S. pressured Caracas to stop sending oil to Cuba and threatened to take it any country that tried to replace it.

SPEAKER_03 0:27

I know many leaders in the region, friend and foe of the Trump administration, who were looking over their shoulder, putting in place contingency plans, wondering if they fell out of favor with the Trump administrators.

SPEAKER_04 0:38

Four months in, the crisis has deepened, and the only tanker to get through came from Russia. Cuba has no oil, and no one inside the government has signaled they're willing to deal. So what's Washington's in-game and what happens to the island while it waits for one?

SPEAKER_03 0:56

Latin Americanists are pretty perplexed at how a Venezuela model could be successful in Cuba, and very skeptical that there is a Delcy with whom the United States could work after the fact.

SPEAKER_04 1:13

Today, Cuba on the Brink. Joining us today is Emily Mandralla, former Deputy Assistant Secretary of State in the Bureau of Western Hemisphere Affairs. Moderating the conversation is Courtney Dockard, President of Network 2020.

SPEAKER_00 1:41

One, bit of a scene setter. What is the current situation in Cuba? We know that there have been near collapses of the national energy grid. So could you just put into context what has happened, what's the state of play right now? But then also to broaden that part out. And if you wouldn't mind, we'd love to hear a little bit about how the long history of US-Cuba relations that we just heard about has shaped this current situation.

SPEAKER_03 2:14

Sure. Thank you, Courtney. And thanks everybody for the opportunity to be here. I'm looking forward to this discussion. So the current situation is really dire, in short. There is a humanitarian crisis on the island. Schools are shuttered. There are periodic blackouts that are scheduled to preserve electricity. And then we have also seen the electrical grid collapse in its entirety many times over the last month, being offline, sometimes for days, while the government seeks to repair it quickly. And we hospitals have canceled surgeries. There is very little by way of public transportation. The cascading effects are tremendous. The trash is piling up in the streets because there's no fuel to provide to the trash collection trucks. There is very little travel or tourism to the island, which is limiting resources further, including to this, the very small private sector that's primarily hospitality facing. I think with power cuts, intermittent water, spoiled food, when electricity goes out, the health sector being severely impacted as well, there's a lot of fear that worse things are around the corner. And your question of how did we get here? It is a crisis that has been a long time in the making, but has been absolutely exacerbated by some recent events since the beginning of 2026. We saw in early 2026 the United States carry out an operation to extract Maduro from Venezuela, bringing him back to the United States to face indictment. And immediately on the heels of that, the U.S. put the pressure on the Venezuelan government to stop providing oil to Cuba. Cuba had long operated beyond its means with respect to fuel. The system was slowly shutting down. But when the US cut off that lifeline from Venezuela, it exacerbated the decline. And then moreover, the United States government put in place an executive order in mid-January to threaten sanctions, threaten tariffs against any country that would provide or sell oil to Cuba. And with that, incoming fuel shipments to the island ground to an entire halt. And that has exacerbated the situation and brought us to the where the situation that I described at the outset. Now, I think your question or your request for a scene setter is important because this is not the US actions in 2026 is by no means happening in isolation. We have a long and complicated, uh, as one could expect, history with Cuba. So I want to take you back very briefly to the 1800s and give a quick overview of what that relationship has looked like so that we can put today in context. So 1800s, tons of American commercial interests in the island. We helped Cuba break free from Spain in 1898, but immediately thereafter imposed the Platt Amendment, which gave uh or reserved the right for the United States to intervene in Cuba whenever we wanted to. Early 20th century, we had a cozy relationship with Cuba. This included a couple of periods of the Batista dictatorship, a huge American corporate presence on the island, and Havana was a popular destination for American organized crime. This all blew up in spectacular fashion in 1959 when Fidel Castro overthrew Batista and aligned Cuba with the Soviet Union, the Cuban Revolution. And what followed was one of the most hostile periods in bilateral relationships in the Western Hemisphere. He saw, as some of you have pointed out, Bay of Pigs, assassination plots, Cuban missile crisis, and a trade embargo that is now over 60 years old and still on the books and part of it codified. The U.S. tried to isolate Cuba economically, diplomatically, and at many points over this 60-year arc, we have thought, as Phoebe pointed out, that we were on the precipice of this working, of the fall, the collapse of the Cuban government, and we could restore, the United States could restore democracy to Cuba. But at every turn, it hasn't worked. Cuba survived the Cold War, they survived the collapse of the Soviet Union, they survived the brutal economic depression that followed the collapse of the Soviet Union. And then when Sidel Castro handed over power to his brother Raul in 2008, the government was still standing. That brings us to 2014. Annie and I were at the State Department. I turned on the news to see that the US and Cuba had announced, this was under President Obama, that they were going to normalize relations. This is December of 2014, an announcement of the intent to normalize relations. And this came with a prisoner swap. It came with a release of some political prisoners in Cuba, some initial good faith gestures to start the conversation to begin to normalize relations. And that culminated in the summer of 2015 when our two embassies opened. They had been acting under the good offices of the Swiss for interest sections, not a formal diplomatic presence in capitals for decades, and they reopened in 2015. Flights resumed. So it was easier for Americans to travel to Cuba, and Cuban Americans could send money back to their family. Obama even visited Havana, the first sitting president to do so in 88 years. I was on that trip helping to wrangle a 50-person delegation from Congress, House, and Senate. And the argument there, the underlying rationale for that approach in the Obama era, was that isolation had not worked. We tried it for six decades. And so we wanted to try something new. And particularly, we wanted to give power to the Cuban people to have control over their future and to allow for the free flow of goods, people, ideas toward that end. So the opening did not survive contact with the first Trump administration. He re-imposed sanctions. I think the post-mortem on that Obama era is that perhaps we didn't move fast enough. And some of that blame, I think, should be put on the uh on the Cuban government as well for being resistant to some of the engagement that the Obama administration offered. But nevertheless, the Trump administration came back in, re-imposed sanctions. The Biden administration loosened things a little bit, but never went fully back to the Obama-era playbook. And then the second Trump term has been even more aggressive and I think encapsulated mostly by events since January of 2026 with the oil blockade that has exacerbated the economic crisis on the island.

SPEAKER_00 9:30

If I may, I'm curious because I understand that during the Soviet era, I can see why relations were fraught, why Cuba would be considered a threat. In the post-Soviet era, it seems like we've gone back and forth based on what you said about the Obama administration's approach. And now I believe Trump has labeled Cuba some sort of extraordinary threat. I'm trying to understand what is what is driving Washington in this regard in terms of its perception of Cuba and whether it's a threat or not, and why we've been taking this very isolationist approach.

SPEAKER_03 10:15

I would say one of the interesting things to observe during the Obama opening was the number of fronts of bilateral cooperation that were stood up during the normalization effort. There were dozens of working groups between the United States and Cuba to collaborate and partner on areas like oil spill planning. In the event that there's an oil spill in waters between the United States and Cuba, how will we handle that? And how would we share information and what do we have at the ready to respond to that in the event that it happens? We've long had cooperation on migration matters. There are supposed to be, and in even in hostile times, there has been a twice-annual migration meeting with officials from the United States government, that of the Cuban government. I think it's been halted under the Trump administration, which is pretty extraordinary because these are the opportunities for lower-level officials to come together and cooperate on things that matter to both of our people. Oftentimes a Cuban Coast Guard cooperates with the U.S. Coast Guard on life-saving matters. This is apolitical and it is purely operational coordination. And even during the Obama administration, there were working groups to connect law enforcement on shared threats or information sharing protocols, counterterrorism working groups as well to do the same. And so while it is accurate that there is Russian presence in Cuba and that Cuba has historically been aligned with countries that the United States has seen as our adversaries, there was a good faith effort and demonstrated interest and action from the part of the Cubans during the Obama opening that was quickly reversed during Trump won. I think your question is also on the one hand, is Cuba a threat, but on the other hand, why does it loom so large in US policy? And my sense is that for a while, Florida as a swing state mattered, and a large diaspora, a large Cuban diaspora resides in Florida. There are many Cuban-American electeds in Congress that wield a lot of power. Many of them sit on influential committees, appropriations committees, foreign relations committees until recently. And that that has also driven conversations in Washington about Cuba. And at base, it comes down to how much the policy apparatus or how much anyone in administration is willing to prioritize Cuba. Because on the one hand, the Cuban diaspora, the electeds that are in prominent positions in Congress are willing to catch all of their political capital in to preserve status quo until there is a democratic opening in Cuba. Whereas those who see the policy of isolation as ineffective and want to try something new to give power to the Cuban people are have to put a whole lot of political capital in order to counter that which is brought by the Cuban DIS.

SPEAKER_00 13:44

Like you just referenced in the Obama administration, maybe the Cuban government was moving too slowly. What does that dynamic look like?

SPEAKER_03 13:52

I wrote an article in El País in mid-February with a colleague of mine, Maria José Espinosa Carrillo, who's a Cuban economist. And because she's an economist, we could say things, we could use economic terms. So I'm going to read you one line from that article and then I'll and then I'll translate it into the way that I speak. So we said it's attempting to treat Cuba's collapse as a sudden inflection point driven primarily by external pressure, but Cuba's current fragility is the result of layered shocks interacting with long-term structural weaknesses. What does that mean? It means both. It is because of US pressure. It is also because Cuba's economy has been weak for a long time. So in bad times, Cuba has been dependent on subsidies. They have been dependent on support from the Soviet Union in the 90s. They had been dependent since the early aughts on Venezuela and free oil or oil in exchange for security support and doctors, kind of oil on trade from Venezuela. And in good times, the economy has been dependent on tourism, remittances, limited self-employment, much of which is hospitality facing. And so even in good times, it is incredibly vulnerable to external shocks, like the pandemic, like changes in US policy, and like in the 90s, the fall of the Soviet Union. So it has been veering toward economic crisis for a while now. And blackouts are not new in Cuba. But what is different is that the sudden action in January from the US government to suddenly stop oil from coming into the US, sorry, into Cuba, ground their electricity grid, ground their oil pumps, ground their hospitals, their schools, their public transit to a halt, and have exacerbated the situation.

SPEAKER_00 15:53

So we've talked a lot about the US action in Venezuela in early January that followed, that was maybe the month and a half after the release of the national security strategy, which has been dubbed the Don Roe Doctrine because of the emphasis on Western hemisphere. I'd be curious to get your take, and I'll put this in a multi-part question, what you think about whether this signals the approach in Venezuela and what they're doing with Cuba now, whether that signals a transition in Washington from more containment to this pursuit of regime change. And I'll just blow that out a little bit to bring in, because nothing operates in a vacuum, the fact that the US is currently conducting operations in Iran that might change the calculus of other leaders. So I'm curious just to a two-part question. What do you think the US strategy is, especially given the national security strategy and what they're pursuing in Latin America? And then how might that be perceived in Cuba given the deviation, let's say, from the Western Hemisphere focus with Iran?

SPEAKER_03 17:03

Uh I think I'm going to take your second question first. So we there's the operation in Venezuela in early January, and it was seen as a tactical success. The military was able to get in, get out, no loss of life from the United States from U.S. military, seize its target. And in the aftermath, they have found a partner in Delcy Rodriguez, a former vice president who've now assumed the role of president. And so we have seen in Latin America circles and even in foreign policy circles, a shorthand reference to what's happened in Venezuela as Trump is in search of his Delhi. And the Venezuela model is governing his efforts elsewhere. And absolutely in Iran, I have heard US government officials say several times that they are in search of a Venezuela model and are looking for their Delhi with whom they can cooperate. In Venezuela, we see that they, the relationship with DELC is in service of reviving the country's petroleum sector, or their oil sector. They have the largest known petroleum reserves in the world, which is apparently the motivation of the US government for the early January operation and its engagement since. And they have set up a model where of profit sharing, where we're encouraging, the United States is encouraging investment and in many in exercising a lot of control over the oil sector, where the oil goes, and uh uh ensiphon some of the profits or sharing some of the profits as well. And the I've heard reference in Iran to a desire to do something similar vis-a-vis the Strait of Hammuz. And it doesn't seem like that's the plan today, although I did see reports that uh the tolling system that Iran has set up will be paid in crypto that's affiliated with the Trump administration. So perhaps that is the model that's going to play out in Iran. But I I have also heard reference to the Venezuela model and in search of a DELC when it comes to Cuba. And there are so many differences between Cuba and Venezuela. There's so many differences between Venezuela and Iran as well. But I it Latin Americanists are pretty perplexed at how a Venezuela model could be successful in Cuba and very skeptical that there is a Delhi with whom the United States could work after the fact. The I think a couple of differences just to highlight, Venezuela has oil. Cuba does not. So it's hard to see what the economic motivator would be in Cuba. Perhaps it's tourism that the revenue would pale in comparison to a revived oil sector in Venezuela. There is, there's the idea of a DELC is is perplexing because Cuba's the Cuban Communist Party exercises so much control over everything in Cuba and has for decades. Whereas in Venezuela, they held elections, democratic elections. They were flawed, but there were elections in 2024. That is recent. There is an opposition, and a credible opposition, and a successful opposition in Venezuela, whereas no such opposition in an organized sense exists in Cuba. There are opposition actors and people who speak out against the government, but they are pretty swiftly suppressed, either because they're jailed or because they are threatened into silence. And another important difference between Cuba and Venezuela is the U.S. authority that governs sanctions. In Venezuela, the United States has exercised sanctions against Venezuela through largely executive power. These are levers that the president can and has pulled to expand and contract and tailor sanctions accordingly in Venezuela. In Cuba, sanctions are codified. And there is some discretion that the executive can enact through regulatory changes or otherwise. But the Helms Burton Act that was passed in the mid-90s immediately after the Brothers to the Rescue shootdown has set out the in-law US sanctions toward Cuba unless and until certain defined actions and steps take place toward a democratic transition. And that is going to really limit the Trump administration's negotiating power with Cuba as they're as they are engaged in apparent negotiations. And then I think to your question, Courtney, of the Monroe Doctrine, one additional thing I'll say it has a very ugly past. I think US diplomats have been trying for decades to overcome that ugly past. It is it smacks of US hubris, a sense that the US can and should dominate. The region, that we have some entitlement to ownership over the region. And I know that, and first of all, it there will be a tale to this, a long tale to this, and the U.S. will be overcoming this period right now in history for generations plural to come. But also, when the Venezuela operation happened in January, I know many leaders in the region, friend and foe of the Trump administration, who were looking over their shoulder and putting in place contingency plans, wondering if they would be next. If the US would take this unilateral action to depose a foreign leader and Maduro was illegitimate, he lost an election, he stayed in anyway. Even still, the leaders in the region were wondering what legal authority we used and whether or not they would be next if they fell out of favor with the Trump administration.

SPEAKER_00 22:52

I am curious to understand how regional leaders and other and beyond are perceiving the latest U.S. actions, both in Venezuela and in Cuba. And in particular, I know that this is a bit of an election year too in some Latin American countries. How is that playing out? Would you mind just going into a little bit more detail?

SPEAKER_03 23:13

Sure. So I think events in Cuba, Cuba's an island and they're pretty self-contained, but nevertheless, events in Cuba uh affect countries, not just in the region, but around the world as well. I think in over the last five years, Cuba has seen a huge outflow of migration. The situation has worsened, quality of life is has declined dramatically. And those who could, who had the means, have left. And I have seen some reports that Cuba's population dwindled from 11 million to eight. And people, many of them came to the United States. Now our borders have hardened. And I understand that much of Cuba's outflow is heading to Brazil, to Guyana, to Spain, to Mexico. And so as the situation worsens, there's a question of what will happen in the migratory landscape in Cuba. And some are very fearful that Cubans could take to boats as they did in the 90s and that you could see a tremendous humanitarian crisis. I do know that because travel has gotten somewhat easier and because air travel has opened up, that there are other experts who assess that perhaps maritime, the maritime route won't be utilized as it was in the 90s, but even still people are watching at space. There are others that have been traditional allies to Cuba. I think Mexico was sending oil. And even after our the United States efforts to halt that oil flow, Mexico has continued to send humanitarian aid, Chile as well, Spain as well. And there is a just because of the 60 years plus of US attempts at isolation, there it has strengthened this cadre of informal allies with Cuba. That has changed as countries change leadership, that there is a global left, mostly a Latin America left, that has stood alongside Cuba in principle. And then there are the historical patrons of Cuba. And really, there are only two that fall into that bucket, and it's Russia and Venezuela. Venezuela is obviously in a tremendously different situation today than it was at the beginning of January, but Repalted all oil and cut ties in other respects as well. Cuba was providing physical security to Venezuelan leadership. Cuba was providing doctors to the Venezuelan people in exchange for revenue, in exchange for oil. And those ties have been cut as well. And then Russia is a little more complicated given I think Russia's influence and relationship with Cuba has ebbed in flowed over the years. But it has certainly uh, I think been in the news recently as it sent a tanker with hundreds of thousands of barrels of crude to Cuba. And there was, you know, everyone lacked with dated breath whether or not that tanker was going to get through, and it ultimately did. And now there are promises of another one to come. And so I think the what's happening in Cuba matters to other countries, but it's somewhat limited because of Cuba as an island. And then with respect to Venezuela and to the Monroe Doctrine more generally, I think countries are in many respects acting out of fear. There are a lot of countries that are tripping over themselves to deliver, to, to partner, to promise, to offer. And we are seeing a strategy that is really pivoting from a US seeking to cooperate and to partner with the region to a use of almost exclusively coercive tools that I think has a real shelf life. I think it's delivering questionable results now, but I think it is absolutely unsustainable in the medium term and probably in the short to medium term too. So it'll be, and I know this is happening all over the world too, not just in Latin America, but I do feel as though it is a it it's happening in a uh a more intense way in the region, given our supposed prioritization of the region, which as Courtney mentioned suffered if if perhaps suffer isn't the right word, but uh after a hot war in the Middle East broke out, it's hard to prioritize Latin America to the extent that that this administration had promised. But but just given the prioritization that we've put, given the attention that Secretary Rubio has as well, uh the coercive approach is on display in the Western Hemisphere.

SPEAKER_00 27:49

You referenced the fact that this Russian oil tanker was let through. That kind of gives a longer, little longer shelf life to Cuba for the moment and perhaps to these talks. But with that being said, what are some of the scenarios that you're foreseeing? Is it going to be like a drip of oil tankers going through? Can the government sustain this US pressure? Are negotiations going somewhere that you think that there is an off-ramp? Or is the island heading to collapse? What what are some of the scenarios that you're turning over in your mind?

SPEAKER_03 28:29

It's a good question. And I absolutely don't have a crystal ball. I will say that at many points in the history and in the historical overview I gave at the top, there have been many points that the U.S. has thought that we were on the precipice of real change, and that hasn't come to be. That said, this time feels like we're on the precipice of, or could be on the precipice of change. And so it has made a lot of Cuba walkers sit up a little straighter and pay a uh a bit more attention. The US has cut off oil, it's given the United States tremendous leverage, but that happened four months ago almost. And we what we have seen is not change necessarily, but a a worsening humanitarian situation that is that is really dire. And so I think in short, if the if things don't change quickly, there's not meaningful effort to in a systematic way address the humanitarian situation, then then things will get worse. And I I there have been efforts from uh humanitarian organizations from other countries, as I mentioned, to send aid, but it is nowhere near enough to address the needs on the island. So I think there are negotiations between the US and Cuba. Both sides have confirmed and then walked back and then confirmed again that there are negotiations. The Secretary Rubio has talked a lot about the need for economic reform in Cuba. There are our economic model is not working, it's broken, we need to see change. I understand that political change is still on the agenda as well, but perhaps on the medium term. But what does that actually look like? And what do negotiations look like? And what could be possible outcomes of these negotiations? I think we could see economic opening, a la the Obama era opening, a allowing for more US investment, allowing for more travel, allowing for a lifting of certain sanctions on the US side, and then the Cubans reciprocating with greater economic freedom on the island for the self-employed sector. We could see demands for release of political prisoners. The Cuban government just two weeks ago announced that they were planning to release a large number of prisoners, but the reports are muddied as to whether these are individuals in prison for political reasons or simply prisoners who are having their sentences commuted. Uh I think, you know, in an ideal situation, the Cuban people would have a lot more power over determining their own future, that they would have the opportunity to elect and choose their leaders. They would have the opportunity to choose their economic paths as well, and that they would have freedom of expression. I uh I it is it's troubling watching the way that the negotiations are proceeding, especially amid such a dire humanitarian situation.

SPEAKER_01 31:22

Thank you, Emily. I really, really appreciate the that overview.

SPEAKER_04 31:33

Thank you for joining us on this episode of Global Insights. You can subscribe to Global Insights on Apple Podcasts, Spotify, or wherever you get your audio. See you next time.