US Threatens Cuba With Trump’s Venezuela Blueprint

Summary

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Big Take: US Ramps Up Threats to Cuba With Trump’s Venezuela Blueprint

Podcast: Big Take (Bloomberg/iHeartPodcasts)
Date: May 26, 2026
Host: David Gura
Featured Guest: Eric Martin (Bloomberg State Department/foreign policy reporter)

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Overview:

This episode dives into the Trump administration’s escalating pressure campaign against Cuba in the wake of its high-profile regime change operation in Venezuela. The conversation explores new US indictments, military posturing, oil embargoes, and the broader geopolitical and humanitarian implications for both Cuba and Venezuela. The hosts unpack the administration’s "Venezuela playbook," its consequences for ordinary citizens, and the risks of further destabilization in the region.

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Key Discussion Points & Insights

1. New US Actions Against Cuba

[01:50–04:25]

• Indictment of Raul Castro: On Cuban Independence Day, the US Justice Department charges Cuba's former President with crimes related to the 1996 shoot-down of civilian planes.
• Military Posturing: US military announces an aircraft carrier’s presence in the Caribbean; reports of increased intelligence gathering and hinting at potential intervention.
  • Quote: “We are announcing an indictment charging Raul Castro…” – David Gura [02:02]
  • Quote: “[CIA Director John] Ratcliffe made it clear that the Cuban government needs to make fundamental changes to take President Trump seriously.” – Eric Martin [04:25]

2. The Venezuela Blueprint & Its Significance

[04:32–05:44]

• CIA Director Ratcliffe visited Cuba in a public show of pressure.
• Trump administration draws overt analogies to its operation that ousted Venezuela’s Maduro:
  • “Look what we did in Venezuela…” – Eric Martin [04:32]
• Debate over risk appetite: Is the Venezuela success emboldening further US action, or is the ongoing Iran war tempering it?
  • Quote: “…the administration may be looking to put another win on the board like was broadly perceived with Venezuela…” – David Gura [05:02]

3. The Oil Embargo and Impacts on Cubans

[03:06–03:50, 08:53–10:49]

• The US has enforced a near-total oil embargo on Cuba since toppling Maduro, Venezuela’s former leader and Cuba’s primary oil supplier.
• Severe blackouts cripple essential services: food production, hospitals, schools.
  • Quote: “You’re hearing stories of people unable to be kept alive on ventilators, unable to get the kind of life sustaining care that they need in hospitals because of these blackouts…” – David Gura [03:36]
• Blackouts have triggered protests, but the regime’s repressive tactics stifle dissent.

4. Broader Strategy: Why Now?

[06:11–08:02]

• The Trump administration's "maximum pressure" on Cuba is part of a stated strategy to counteract “foreign malign actors” (China, Russia, Iran) in the Western Hemisphere.
  • Quote: “This has been a goal of the Trump administration...principally have identified China, Russia, and to some extent Iran as well.” – David Gura [06:11]
• Venezuela served as Cuba’s patron, sending subsidized oil in exchange for intelligence support.
• The theory: Encourage private sector growth to spur political opening; the US is pressuring countries and companies globally to avoid supplying oil to Cuba.

5. Sanctions: Effectiveness and Humanitarian Fallout

[09:09–10:49]

• Sanctions inflict economic pain, but history shows Cuban and similar regimes can weather extreme hardship while populations suffer.
• Risk of humanitarian crisis and mass migration—20% of Cubans have already left in recent years. US faces risk of migration surges to its shores as conditions deteriorate.
  • Quote: “Do these sanctions actually make things so bad that it spurs a very immediate national security threat in terms of overwhelming US shores with migrants?” – David Gura [10:49]

6. Internal Response in Cuba

[10:49–11:56]

• Protests do occur (Party HQ attacked, fires set), but authorities maintain tight control.
• The regime’s pervasive surveillance and history of suppression mean large-scale dissent is unlikely, despite widespread suffering.

7. US Appetite for Military Action and Political Calculations

[11:56–12:41]

• Broader context includes the ongoing (and unpopular) Iran war and looming US midterm elections.
• Domestic political pressures may affect willingness to escalate in Cuba.

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On the Ground in Venezuela: Post-Maduro Changes

[15:25–21:47]

1. Reopening and Cautious Optimism

• First US commercial flight to Venezuela since 2019 signals attempts at normalization; American and United Airlines resuming direct flights.
  • Quote: “It’s one of the most visible ways yet...of a return to normal, a return to pre Maduro or pre Chavez days.” – David Gura [16:28]

2. Reality Check: Economics and Society

• Hyperinflation (>600%) continues, wages remain extremely low. Everyday life remains hard despite optimism.
  • Quote: “Price of a cup of coffee [has increased] sixfold in just one year.” – Eric Martin [16:51]
• US "running Venezuela": The Trump administration is dictating many day-to-day policy decisions.
  • Quote: “The regime really is being responsive to a lot of the demands and the orders being sent from Washington…” – David Gura [17:10]

3. Investment and Reform

• Some foreign (notably oil and mining) investments returning, but skepticism remains due to political instability and lack of legal guarantees.
• Reforms may not be irreversible; transition to full democracy is required for real investor confidence.
  • Notable moment: Delsey Rodriguez, President of Venezuela, answers a question about elections: “I don’t know, sometime.” – [20:59]

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Lessons for Cuba & Broader Foreign Policy

[21:47–23:33]

• Maduro’s ouster in Venezuela demonstrates US willingness to use force to achieve policy goals, not just diplomacy.
  • Quote: “Trump prefers diplomacy. He would prefer to make a deal, but he’s not afraid to use force. And the attacks on Venezuela to remove Maduro, the bombing campaign, and the war begun in Iran in late February is another data point.” – David Gura [22:20]
• The message to Cuba is clear: US threats are credible, and use of military force is on the table.

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Notable Quotes & Memorable Moments

• “Look what we did in Venezuela…” – Eric Martin [04:32]
• “You’re hearing stories of people unable to be kept alive on ventilators, unable to get the kind of life sustaining care that they need in hospitals because of these blackouts…” – David Gura [03:36]
• “Do these sanctions actually make things so bad that it spurs a very immediate national security threat in terms of overwhelming US shores with migrants?” – David Gura [10:49]
• “I don’t know, sometime.” [on Venezuelan elections] – Delsey Rodriguez [20:59]
• “Trump prefers diplomacy… but he’s not afraid to use force.” – David Gura [22:20]

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Important Timestamps & Segments

• [01:50] Indictment of Raul Castro and renewed US threats
• [03:06–03:50] Blackouts ruining Cuban infrastructure and healthcare
• [04:04–04:32] CIA Director’s visit as signal of potential military action
• [04:32–05:44] Venezuela operation as model; analyzing administration motives
• [08:02–10:49] Cuba’s elite, economy, mass emigration, and sanctions
• [15:25–21:47] Eric Martin’s Venezuela trip: normalization, ongoing struggles, investment outlook, and the future of governance
• [21:47–23:33] Lessons for Cuba – US resolve, use of force, and what to expect next

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Transcript

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[David Gura]

Bloomberg Audio Studios Podcasts Radio News They've

[Commercial Announcer]

really lost control of Cuba.

[Eric Martin]

The president's been clear he has other options.

[Sonesta Hotel Advertiser]

I'm not going to elaborate on what

[David Gura]

those are, but everybody knows what those

[Eric Martin]

the Trump administration is ratcheting up pressure on Cuba.

[David Gura]

We are announcing an indictment charging Raul

[Eric Martin]

Castro On May 20, which is Cuban Independence Day, the Justice Department indicted Cuba's former President Raul Castro in connection with the 1996 downing of two civilian planes. The US military announced an aircraft carrier is in the Caribbean, and Secretary of State Marco Rubio shared a video message online offering everyday Cubans the prospect of a relationship with the US and blaming Cuba's troubles on the island's ruling elite. Rubio said. Those who control your country have plundered billions of dollars, but nothing has been used to help the people. The Trump administration's latest pressure campaign comes five months into its near total oil embargo of Cuba, which started when the US Took Down Nicolas Maduro, the leader of Venezuela, Cuba's main international patron and its biggest source of oil.

[David Gura]

And this is not just fuel for automobiles.

[Eric Martin]

That's Eric Martin who covers the State Department and foreign policy for Bloomberg.

[David Gura]

This is oil that goes into electricity. They don't have the fuel that they need for food production, processed foods. They've had hospitals, schools that have urgent need for electricity that can't get it.

[Additional Reporter or Announcer]

Blackouts across the country have sparked protests. Cubans banging on pots and pans, shouting turn the lights on.

[David Gura]

And so you're hearing stories of people unable to be kept alive on ventilators, unable to get the kind of life sustaining care that they need in hospitals because of these blackouts and this electricity shortage.

[Eric Martin]

All these latest turns, the indictment, the forceful rhetoric and an unprecedented visit to the island by CIA Director John Radcliffe earlier this month. Eric says that's widely seen as a signal the US Is ready to use military force.

[David Gura]

We've seen reports of an increase in intelligence gathering flights around the island. We've also seen even publicly President Trump talking about the US Military carriers like the Lincoln could stop off in Cuba on their way back from Iran.

[Eric Martin]

Eric says that Radcliffe during his visit made it clear that the Cuban government needs to make fundamental changes to take President Trump seriously.

[David Gura]

Ratcliffe talking about US Willingness to partner with the Cuban regime on economic and political changes to help the Cuban people. But if you're not willing to accept our help and you think that the alternative is maintaining the status quo, look what we did in Venezuela at the

[Additional Reporter or Announcer]

beginning of the year after months of buildup. At 2:01am local time today in Caracas, Venezuela, US Delta forces slipped into the home of dictator Nicolas Maduro.

[David Gura]

There's two schools of thought among analysts here, one of which is that the Iran war is a cautionary tale that might make the administration reticent to get involved physically in Cuba in terms of any kind of military activity. But another is that as a political point that the administration may be looking to be able to put another win on the board like was broadly perceived with Venezuela, which was a two and a half hour operation to remove Maduro and that that could actually increase the risk appetite to do something in Cuba.

[Eric Martin]

I'm David Gura and this is the big take from Bloomberg News today on the show, the Trump administration's escalating threats against Cuba and how the U.S. s attempt at regime change in Venezuela is playing out in that South American country. Eric, the US has had an embargo in place on Cuba for more than six decades. Why is The US Amping up the pressure so much right now.

[David Gura]

This has been a goal of the Trump administration articulated in the National Security Strategy in December to counteract foreign malign actors in the Western Hemisphere. They principally have identified China, Russia, and to some extent Iran as well. These reports of Chinese presence in Cuba being one thing that the administration has identified indefinitely, pervasively in Venezuela. We saw a lot of Iranian actors in Venezuela. We saw a great number of Cuban intelligence agents living in Venezuela in recent years. For a long time, the understood arrangement was Venezuela would send this subsidized oil to Cuba to keep the lights on, to keep the economy going. And Cuba sent Venezuela doctors, but also in particular, spies and intelligence agents.

[Eric Martin]

It seems like that moment in early January when the US Went in and removed Nicolas Maduro was something that was closely watched by the Cubans.

[David Gura]

Absolutely. That was the pivot point. You had this pressure building for years, really, since the COVID 19 pandemic January 3rd was a pivot point for Cuba because Venezuela has filled this role that Cuba has needed for decades of a patron state that previously it was the USSR until the fall of the civil war, Soviet Union. And now they're facing a similar challenge because the US President Trump in January threatened with tariff, secondary tariffs any country that was supplying oil to Cuba. But the private sector has been able to buy from American and foreign companies, and that's been a big push from the administration. Is the theory that if you open the private sector and you get the private sector to grow, that that will result in both an economic but also political opening.

[Eric Martin]

How has the US Been ratcheting up pressure on Cuban officials?

[David Gura]

It's really the Castro family that still controls Cuba 67 years after Fidel and Raul led their revolution to topple Batista, who had been supported by the US in 1959. The understanding is that the Castro family, this company that they set up called Gaesa, which is a military conglomerate and really runs the economy on the island, is the real power broker on the island. So what we've seen with some of these steps, including the indictment of Raul Castro, is setting out a legal case, as we saw with Maduro. So what is the action that follows from that and drawing connecting the dots to a potential military intervention of some kind, as we've seen lots of reporting from lots of outlets in Cuba.

[Eric Martin]

So the oil embargo, the sanctions policy that's been wielded in Cuba, the messaging from John Ratcliffe and others about what military threat might be there. I'm curious what your assessment is of how Much that's advancing the administration's goals here of getting regime change in Cuba.

[David Gura]

This is a problem we've seen around the world with sanctions, which is that they impose economic pain, but the ability of regimes to find ways around them and find ways to survive even as the population suffers in misery. Cuba endured this incredibly harsh and dire economic environment in the 1990s after the end of Soviet support and the economy shrank by a third. People point to the 1990s, this decade long special period, as it's called, in terms of pointing out how much economic pain the regime is willing to endure or is willing to impose on Cuban citizens that in order to stay in power. That's part of the concern here is do you squeeze things so much, do things become so bad that you have a humanitarian crisis that prompts people to leave the island 90 miles off Florida's coast, and now you have a crisis of undocumented migrants coming to the U.S. we've already seen about 20% of Cuba's population, several couple million people who have left the island in recent years because of the lack of opportunity, lack of hope, and inability to envision the future. Cubans became one of the largest groups arriving as undocumented migrants to the U.S. southwest border. And so do these sanctions actually make things so bad that it spurs a very immediate national security threat in terms of overwhelming US Shores with migrants?

[Eric Martin]

Do we have a sense of how Cubans are responding?

[David Gura]

Well, we have seen sporadic protests on the island. We've seen in one location that the Communist Party headquarters got attacked. We've seen people setting fires and otherwise creating unrest in the streets in recent months. But it's hard to overstate the repressiveness of the regime and their ability to muzzle the these kinds of popular outcries. This is a regime that for more than six decades has had a high degree of visibility into people's lives, ability to spy on people, encourage people to turn in their neighbors who they think are being disloyal to the revolution. And so despite the suffering on the island, the regime has shown itself effective in the past in being able to maintain control and in spite of conditions that in a lot of countries would spur people to rise up or to protest in more visible ways as we

[Eric Martin]

look ahead to what might happen here. Obviously you had what happened in Venezuela. The war in Iran continues. Does the US have the bandwidth at this moment in time to take military action on Cuba?

[David Gura]

Well, part of that is a political question in terms of how the Iran war and the efforts to bring it to a resolution are being perceived. And of course, we have midterm elections in the US in early November. We've seen polling that shows the Iran war is unpopular. So part of this is a political question about how much can the American electorate tolerate in terms of foreign entanglements.

[Eric Martin]

When we come back, Eric Martin takes us along as he travels to Venezuela to see what's changed since the US removed the country's president.

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[Eric Martin]

On April 30, passengers on American Airlines Flight 3599 left Miami for Simon Bolivar International Airport outside Caracas. It was the first commercial flight from the US to Venezuela since 2019. Bloomberg's Eric Martin was one of the passengers.

[David Gura]

We took off from Miami to a lot of festive atmosphere. They had a big archway of balloons in Venezuela's yellow, blue and red flag colors, traditional Venezuelan food, arepas. On behalf of President Jensey Rodriguez and

[Commercial Announcer]

the government of the Bolivar Republic of

[David Gura]

Venezuela, you are very welcome to Caracas.

[Eric Martin]

Travelers from the US To Venezuela used to have to go through third countries like Panama, but the US State Department took the country off its do not travel list in March and now American Airlines is offering two daily flights from Miami. And United Airlines announced plans to start operations to the country from Houston this summer.

[David Gura]

It's one of the most visible ways yet that we've seen in terms of creating this image of a return to normal, a return to pre Maduro or pre Chavez days. But still there are Venezuelans in exile who live in fear of the government and are afraid that if they went back to their country they would be arrested and thrown in jail.

[Eric Martin]

Eric, you've written about frustration over wages and living conditions, the price of a cup of coffee increasing sixfold in just one year. Venezuela still has one of the world's highest inflation rates, over 600% in April. Talk a bit about this disconnect, the way that things are on the ground versus this perception that it's once again open for business.

[David Gura]

People are still upset about the the low wages, low incomes for people in Venezuela. There's this big disconnect between hope for the future, which people have now in a way that they didn't have nearly as much before January 3rd, and the experience of the current reality, which is while you have companies who are down there and they're exploring and you have some of the first investments and you have lots of money that is coming into the US treasury fund and going to the government to pay services and to pay social services in Venezuela, that this economy that has been declining for years can't be just turned around in, you know, a bit less than five months since the removal of Maduro. President Trump on January 3rd talked about the US will be running Venezuela prompted many questions about exactly what does that mean? And my reporting has been that the regime really is being responsive to a lot of the demands and the orders being being sent from Washington as To what policies to adopt, what decisions to take.

[Eric Martin]

The Trump administration has reopened its embassy in Venezuela and re established diplomatic relations as well. To what degree is this a country open for business? Who is investing there? What kind of investments are being made?

[David Gura]

Well, we've started to see mainly independent oil companies and miners, gold. We've seen, we've also seen exploration, interest in producing coal. Venezuela was always a commodity driven economy. That was in some ways both the blessing and the curse of Venezuela. When you're living large, it's easy to not plan for a rainy day. And that's been a problem for Venezuela. Ran into financial fiscal problems in the 1980s, 1990s. But at the same time, these oil companies are careful about what they're going to do. We've seen Chevron getting more involved because they have a history in Venezuela. They've been one of the few that have been able to maintain production in recent years. But others who are more cautious and are a bit skeptical about getting back into Venezuela, given limited resources for them globally in capital and given all kinds of competing opportunities around the world. We've seen President Trump talking about billions of dollars that would go back into Venezuela and thus far we've seen a fraction of that, although those decisions also take time and companies do their due diligence. But there's a bit of a catch 22 at work here, which is that there are some investors who say they're not going to feel comfortable investing. But until there is a real reform of the political system and until there's elections in the transition to democracy and greater transparency of the rule of law, they've passed an important hydrocarbons law, they've done some reforms to make it more investor friendly. But I was speaking with someone down there who said, listen, what's happened so far domestically in Venezuela, none of it is, are changes that could not be at some point reversed if the dynamic changes. And the only way that you get truly solidifying all of the changes is if the country returns to democracy in a way that investors can trust and in a way that investors see the rule of law. And the big open question is how quickly can that be reasonably done? Are we talking about a period of a few months or more likely a year or a couple of years? We actually met Delsey Rodriguez very briefly and one of my colleagues said, President Rodriguez, when will there be elections in Venezuela? And she answered in English, I don't know, sometime. She said, I don't know sometime. And that, that, that was kind of a, a tell as to the strategy for the current government, you know, which is largely still a post Maduro government. The thing a lot of people are looking for is when will it be a transition, not in just the individuals running the country, but more of a cultural transition from the current regime.

[Eric Martin]

Eric, let me ask you lastly what the lesson here is for Cuba and its future as it looks to what's going on in Venezuela. Obviously there are a lot of differences in these two countries, but how are you looking at them side by side moving forward?

[David Gura]

I think Maduro's removal from Venezuela has widened the overton window of outcomes that we can expect from US Foreign policy and also from missions that US Foreign policy would undertake. Even as the US Was amassing naval assets and military assets in the southern Caribbean in the final months of 2025, there were plenty of people who said, this is all saber rattling. This is all for show. The US Is never going to act against Venezuela. They're looking just to cut a deal. And the point that's been underlined for me many times by people in the Trump administration is that Trump prefers diplomacy. He would prefer to make a deal, but he's not afraid to use force. And the attacks on Venezuela to remove Maduro, the bombing campaign, and the war begun in Iran in late February is another data point. Last June's bombing of Iran's nuclear sites is yet another data point. And essentially the message from these people in the administration is take seriously the threat of using force to achieve foreign policy outcomes. So I think that's the message that I hear most frequently in my reporting. And I think it's the message that Director Radcliffe sent to Cuba when he was there.

[Eric Martin]

This is the Big Take from Bloomberg News. I'm David Gura. To get more from the Big Take and unlimited access to all of bloomberg.com, subscribe [e-mail] podcastoffer if you like this episode, make sure to follow and review the Big Take. Wherever you listen to podcasts, it helps people find the show. Thanks for listening. We'll be back tomorrow.

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