Cuba 'very close' to regime change: John Bolton on Trump, Venezuela and Iran

Summary

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Battle Lines – Cuba 'Very Close' to Regime Change: John Bolton on Trump, Venezuela, and Iran

Podcast: Battle Lines (The Telegraph)
Date: February 27, 2026
Host: Venetia Rainey
Guests: Lily Shanaher (Foreign reporter), John Bolton (Former US National Security Advisor)

Episode Overview

This episode zeroes in on the rapidly unfolding crisis in Cuba, intensified by America’s latest strategies of economic pressure under President Trump. With the recent capture of Venezuela’s Nicolas Maduro—Cuba’s key regional ally—and tightening US sanctions, the panel examines if Cuba’s communist regime could finally be on the verge of collapse. Host Venetia Rainey explores the historical roots of the standoff, analyzes current US strategies, and gains insider insight from John Bolton, Donald Trump's former National Security Advisor, about possible regime change in Cuba, implications for US foreign policy, and parallels with Iran.

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Key Discussion Points & Insights

1. Historical Context: The US and Cuba’s Enduring Standoff

• Cuban Revolution & US Backlash (05:20–06:54)
  • Before 1959, Cuba was seen as a US "playground"—economically dependent, socially influenced.
  • The revolution installed Fidel Castro’s Leninist-style communist regime, breaking from US influence.
  • Immediate US sanctions and severed diplomatic ties hardened the conflict, leading to events such as the Bay of Pigs invasion, which Lily Shanaher calls “a massive foreign policy embarrassment for the US” (06:54).
• Post-Castro Leadership
  • The transfer from Fidel to Raul Castro, then to Miguel Diaz-Canel in 2019, marked a PR shift but not a substantive regime change. Diaz-Canel lacks the charisma and revolutionary credentials of the Castros, leaving the regime ideologically firm but more brittle (07:16–09:01).

2. Cuba’s Current Crisis: Economic Breakdown and Political Pressure

• Energy Blockade & Humanitarian Catastrophe
  • Since January, Trump’s “oil blockade” has pushed Cuba to “total breaking point,” cutting off Venezuelan support, triggering blackouts (up to 24–60 hours in some regions), food shortages, and mounting trash (11:41–13:20).
  • UN warnings of “humanitarian collapse.”
  • “It’s probably the worst crisis it’s ever seen,” says Shanaher (11:50).
• China & Russia’s Support
  • Both provide humanitarian aid and economic lifelines but are limited by their own priorities; China’s solar investments contrast with Russia’s overwhelmed focus on Ukraine (10:03–11:41).
• Potential for Mass Exodus
  • Cuban government has traditionally eased tension by allowing emigration in crises, but Trump’s new policies have “severed” those pathways (13:27), risking instability in the US and Mexico.

3. Nature and Stubbornness of Cuba’s Regime

• Dictatorship Comparison (09:01–09:31)
  • Cuba is “a coalition basically between the Communist Party and the military”—no press freedom, political prisoners, and political dissent is “quickly stamped out.”
• Echoes of Entrenched Iran
  • Both regimes are described as “entrenched” with “true believers,” resistant to outside pressure, and surrounded by heavy propaganda (16:24–17:34).

4. John Bolton Interview: Regime Change, US Strategy, and Global Risks

a. “Cuba is Very Close” (20:52–21:37)

• Key Quote:
  • “I do think we’re very close. Cutting off oil supplies has made it very, very difficult for the Cuban economy... With the Maduro regime in Venezuela sort of neutralized... if we complete the job of regime change in Venezuela... Cuba could be next.” —John Bolton (20:52)
• Bolton Critiques Trump’s Approach
  • Trump “couldn’t make up his mind” and “didn’t do enough” during his first term (21:55).
  • Bolton: “Trump doesn’t specialize in hard work. He wants quick and easy ‘one and done’ sorts of things. That’s not very often the case when you’re trying to do a regime change operation.” (23:12)
• Marco Rubio’s Influence
  • Rubio (Secretary of State, son of Cuban immigrants) is seen as a major operator behind the current aggressive approach (22:35).

b. Paths Forward and Challenges for Cuba (23:12–24:09)

• No Organized Opposition
  • Bolton sees a likely scenario of “some kind of caretaker government that continues to collect the trash and so on,” but notes the regime’s resilience and the unique potential of Cuban Americans to rebuild quickly.
• Cuba’s Strategic Threat
  • Historical and current fears around Cuban “subversion,” biological weapons research, and potential to host Chinese intelligence installations (24:34).
  • Monroe Doctrine invoked as a justification for US involvement: “It’s keeping meddlesome foreigners out.” (24:34)

c. China, Russia, and the Domino Effect (25:21–26:18)

• The “Troika of Tyranny”
  • Bolton posits if Venezuela collapses, Cuba and Nicaragua might soon follow—undermining Chinese and Russian influence.
  • China’s deep involvement in Venezuela’s oil means Cuban instability is a strategic setback for Beijing.

d. Comparisons to Venezuela & Iran (26:33–35:06)

• Venezuela: Incomplete Regime Change
  • Decapitation (Maduro’s removal) “brilliant military maneuver” but failed to bring true regime change (27:46).
  • Authoritarian remnants (like Delsey Rodriguez) remain in power, while the true opposition is sidelined.
• Military Options and Risks in Cuba
  • Precision US military action, as seen in Venezuela, possible but risky; economic and political pressure likely to remain the main tools, especially with Trump distracted by Iran (29:47–30:34).
• Iran: Next Flashpoint?
  • Bolton warns Trump “doesn’t know what he wants to do” on Iran and acts “transactionally” (32:04–33:30).
  • Advocates regime change in Iran, citing youth, women, and ethnic minorities’ opposition as a moment of vulnerability, but warns of possible civil war and regional instability (33:45–35:06).

e. Insights on Trump’s Foreign Policy Style (36:19–37:31)

• No Coherent Strategy
  • “He does not have a national security grand strategy. He doesn’t even do policy... It’s totally transactional. Every day is a new day. Every deal is a new deal.” —John Bolton (36:30)
• National Security Documents
  • Bolton: “You’ve read the National Security Strategy. I’ll bet you a pound he hasn’t. He didn’t read it in the first term. No reason to start now.” (37:22)

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Notable Quotes & Memorable Moments

• “Cuba has essentially been strangled by the US for around 80 years.” —Lily Shanaher (11:50)
• Venetia Rainey: “What sort of dictatorship is this? ...We all know where power really lies.” (09:01)
• Bolton on US-Cuban Exile Power: “There are millions of Cuban Americans and Cuban exiles 90 miles away... This is going to be the quickest rebuilding, the quickest recreation of a government that anybody has ever seen.” (23:21)
• On Authoritarian Stability: “If there’s one thing you can say about authoritarianism, it’s stable. Boy, it is really stable.” —John Bolton (27:46)
• On Trump’s Decision-Making: “It’s, in a sense, like watching a roulette wheel. We’ll know what it is when it happens.” —John Bolton (35:24)

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Key Timestamps

• 05:20–07:02: Cuba’s pre-revolution history and the dawning of the US–Cuba standoff
• 09:01–10:03: Structure of Cuba’s authoritarian regime; comparisons to other dictatorships
• 11:41–13:27: Current severity of Cuba’s humanitarian crisis & migration risks
• 16:24–17:34: Regime resilience: parallels between Cuba and Iran
• 20:52–24:09: John Bolton on the nearness of regime change, Trump’s first term, the Cuban-American role
• 25:24–26:18: China and Russia’s stakes in Cuba and Venezuela
• 27:46–29:47: Venezuela’s “decapitation” and limits of regime change as a blueprint
• 29:55–31:48: Prospects for military intervention in Cuba
• 32:04–35:06: Iran’s instability, Bolton’s regime change advocacy, risks for Trump policy
• 36:30–37:31: Trump’s lack of grand strategy and transactional diplomacy

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Episode Tone

• Analytical but urgent, occasionally critical, especially in Bolton’s candor about Trump’s impulsiveness.
• Nuanced historical perspective, factual but with pointed, sometimes darkly humorous, commentary.

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Final Takeaways

• Cuba’s Regime Is Highly Stressed: Economically pressured and diplomatically isolated; yet history and ideology mean a sudden collapse is not inevitable.
• Trump’s Foreign Policy: Bold but Haphazard: Driven by political opportunism and personal deals, with little long-term planning or ideological coherence.
• Bolton Stresses Planning: Successful regime change requires granular groundwork; “one and done” interventions rarely achieve full transformation.
• Broader Implications: Cuba’s fate is intertwined with regional dynamics, US electoral politics, Chinese/Russian interests, and the evolving American approach to global authoritarianism.

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This episode is essential listening for those tracking Caribbean geopolitics, US foreign policy, and the global contest for influence between great powers. The presence of John Bolton gives rare, unvarnished insights into the pressures and perils behind contemporary regime change calculations.

Transcript

[Lily Shanaher]

Foreign.

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[Lily Shanaher]

Here's a show that we recommend.

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Howdy, howdy ho and welcome to Fantasy Fan Fellas. I'm Hayden, producer of the Fantasy Fangirls podcast and your resident lover of all things Sanderson.

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[John Bolton]

Hey hey.

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And along the way we'll do character deep dives, magic explainers, and Steven will even try to guess what's next. Spoiler alert. He'll be wrong.

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[John Bolton]

Acast.com. Trump doesn't specialize in hard work. He wants quick and easy one and done sorts of things. That's not very often the case when you're trying to do a regime change operation.

[Unnamed US Official]

We will measure our success not only by the battles we win, but also by the wars we end.

[John Bolton]

Right now all eyes are on Washington, but who's actually watching Europe at the moment?

[Lily Shanaher]

The deepening ties between China, Russia and North Korea would certainly have some in Washington concerned.

[John Bolton]

And then Daddy has to sometimes use

[Lily Shanaher]

strong language to do.

[Unnamed US Official]

We're going to run the country until such time as we can do a safe, proper and judicious transition.

[Venetia Rainey]

The IDF will continue to uphold the ceasefire agreement and will respond firmly to any violation of it. I'm Venetia Rainey and this is Battle lines. It's Friday, February 27, 2026. America might be on the brink of achieving a decades old foreign policy toppling Cuba's communist regime. From the Bay of Pigs to crippling sanctions over the decades many US Presidents have tried to get rid of the Castros revolutionary single party state. Cuba has always resisted. But the stunning capture of Cuba's main ally, Venezuelan leader Nicolas Maduro, at the beginning of January has changed everything.

[Unnamed US Official]

Cuba is ready to fall. You know, yes, Cuba looks like it's ready to fall. I don't know how they. If they can hold out, but Cuba now has no income. They got all of their income from Venezuela, from the Venezuelan oil. They're not getting any of them. And Cuba literally is ready to fall. And you have a lot of great Cuban Americans that are going to be very happy about this.

[Lily Shanaher]

You were just talking about Cuba and what could come next there. Are you considering US action in Cuba?

[Unnamed US Official]

We're not. I think it's just going to fall. I don't think we need any action. It looks like it's going down. It's going down for the count. You ever watch a fight? Yeah, they go down for the count. And Cuba looks like it's going down.

[Venetia Rainey]

Since the beginning of this year, Trump has effectively imposed an oil blockade on Cuba, creating an energy crisis and bringing the country to its knees. Residents are facing rolling blackouts, food shortages and piling up rubbish. Trump has urged Cuba to make a deal before it's too late. China and Russia, Cuba's backers, are watching closely for the potential of military action that repeats what happened in Venezuela. And this week, US Secretary of State Marco Rubio is in the Caribbean to hold talks with leaders who are warning that Cuba's growing humanitarian crisis could destabilise the entire region. Many believe that Rubio, the son of Cuban immigrants, is behind all of this. But this aggressive stance towards Cuba's Communist regime is not new. It was also a hallmark of Trump's first term in power. So later on, I'll be speaking to John Bolton, Trump's security adviser during that first term, who famously labelled Cuba and Venezuela as part of a troika of tyranny. I'm going to be asking him what risk Cuba poses to the us, why Trump thinks regime change is necessary and what options the US administration will be considering right now. Plus, just because it's John Bolton, I'm going to talk a bit about Iran and the potential looming war there. But first, to understand the history behind Cuba, I spoke to our foreign reporter, Lily Shanaher. Lily, welcome to battlelines. You've studied Cuba, you've been there, you speak Spanish, you. I'm going to put you a bit on the spot here, but just give us a potted history of Cuba's communist regime.

[Lily Shanaher]

Cuba before the revolution was, some experts would say, essentially a playground of the us. It's a beautiful island, beaches are second to none. And it was used by everyone from Al Capone to Ava Gardner as a holiday destination. There were brothels, mafia casinos, and it was kind of a puppet of the US with the last dictator, pre revolution being Fulgencio Batista. Obviously when Fidel Castro and Che Guevara, after a lot of battles, put it in a nutshell, ousted Fulgencio Batista and he fled in 59, they tried to remove this US influence from the country. So shutting down mafia owned casinos, shutting down brothels, imposing communism they were. And a sort of Leninist style politburo, a new sense of government. The backlash from the US was immediate. In 1960, Eisenhower severed diplomatic ties, put on sanctions, froze all Cuban assets on American soil as well. And from there the kind of cold war between Cuba and the US began and it's just continued. We obviously had the Bay of Pigs invasion.

[Venetia Rainey]

Just remind our listeners briefly, because Bay of Pigs is something we hear chucked around a lot. Just remind our listeners what that was.

[Lily Shanaher]

So the Bay of Pigs invasion took place in 61, planned by Eisenhower. It was an attempt to overthrow the government and as there were previous ones before, and it failed spectacularly and was

[Venetia Rainey]

a massive foreign policy embarrassment for a

[Lily Shanaher]

massive embarrassment for the US who has obviously completely out rivals Cuba, even when it had the support of the ussr.

[Venetia Rainey]

So Fidel Castro's in power and then his brother Raul Castro, and then Raul steps down in 2019 to make way for Miguel Diaz Canel. First guy to not have a Castro surname in many decades, as you say, in the first time in the Cuban Communist regiment. Does this change things much?

[Lily Shanaher]

I mean, in terms of pr, it massively does, because Fidel, he is the leader of the revolution. He always didn't want to create a cult personality. So if you go to Cuba, you won't see many monuments to him or recognition to him. He has a small tomb, especially compared to Camila Cinfuegos, another revolutionary, and Che Guevara. But he had this level of charisma that makes him world famous. Whether you agree with him or fervently disagree with him, you cannot deny that he had that charisma. And the Castro legacy continues. But Miguel Diaz Canel, from what I gather, just doesn't have the same charisma, the same level of charm that helped Castro get people through really difficult times, such as the fall of the Soviet union in the 90s, which led to the special period, which was a time of economic crisis. Similar, but not as bad as what we're seeing right now. And so Diaz Canal, he is trying to put on a defiant front and he's gathered people and there have been anti imperialist, anti US marches throughout Havana. But I think one of the issues is that he just doesn't carry that same charm and that same importance as the Castros did and as the Castro name, you know, Raul is in his 90s, Fidel died many years ago now. Those two brothers, their legacy kind of dies out. And the people who were children of the revolution and were able to enjoy the promises that it did bring, socialism did bring, it had the highest literacy rate, higher than the us, Better medical standards, unparalleled really around the world, especially compared to its, you know, economic difficulties from the U.S. sanctions. And it had a higher life expectancy than the US at times.

[Venetia Rainey]

So can we still call this a dictatorship? I know it's a single party state. No opposition is allowed. What sort of dictatorship is this? Can you sort of compare it to others that our listeners might be more familiar with? You know, North Korea, Russia?

[Lily Shanaher]

There are elections and it's a coalition of factions essentially in the government. So I would say it counts as a dictatorship in the same way that perhaps Russia is a dictatorship. It's not actually one. And there are votes, there are elections,

[Venetia Rainey]

as you say, and nominal parties that can stand. But we all know where power really lies.

[Lily Shanaher]

Yeah, it's a one party state. There's a coalition basically between the Communist Party and the military that runs everything. Gaissa, which is the military conglomerate, runs tourism and is immensely powerful as well. It's a highly authoritarian government, I think, which leads to accusations of dictatorship because there is basically no press freedom. It's one of the worst countries in the world for press freedom. There are around a thousand prisoners, political prisoners, according to some estimates. Any kind of political dissent is quickly stamped out.

[Venetia Rainey]

And they're communists. Do they have close ties with China?

[Lily Shanaher]

Very close ties with China and Russia. Even after the fall of the ussr, Russia remained a close ally of Cuba and in fact has been helping it out during its crisis at the moment providing humanitarian aid, obviously diplomatic support, and is considering sending fuel, although the US will probably just take the tanker, which undoubtedly will be sanctioned. China has also massively invested in Cuba. It's providing humanitarian aid at the moment, like tons and tons of rice, for example, and diplomatic sentiment. It's also been investing in recent years in solar power. Cuba is a very hot country. It can only provide around 30% of its fossil fuel. And its crude oil is very complicated to cultivate. And all of its fuel stations are completely decrepit, so it's going to need to turn to renewable sources. So it's got some wind farms and solar panels, and China at the moment is overproducing solar panels in order to help it. So I would say Russia at the moment is too concerned with Ukraine to ever properly get involved with Cuba, and it doesn't stand to benefit from that much except a kind of middle finger to the US So I believe that China will stand to be one of its closest allies, especially as Latin America is increasingly receiving threats from Trump. For example, Mexico, Claudia Sheinbaum was a massive ally of Cuba and provided a lot of oil, helping to fill the gap after the fall of Maduro. But she's basically been scared off as well. She's trying to diplomatically work a way around sending humanitarian aid and fuel. But with Trump's threats just sweeping over Latin America, I think China's their best bet.

[Venetia Rainey]

How severe has it been for Cuba? Just give us a sense of how bad this crisis is. In the history of Cuban crises, and they've dealt with a lot of pressure from America. Right.

[Lily Shanaher]

Cuba has essentially been strangled by the US for around 80 years. It let up with Barack Obama when he actually went onto the island and tried to resume relations. But since Biden as well, somewhat. But since Trump's got back in, there is absolutely flexibility. Sources I've spoken to on the island and in government say that it's at least difficult, AKA it's probably the worst crisis it's ever seen. The UN has warned that it's leading towards humanitarian collapse. The US Department of the treasury yesterday said it would actually consider authorizing companies seeking licenses to resell Venezuelan oil for commercial and humanitarian use.

[Venetia Rainey]

I saw that in Cuba, kind of u turn right. Well, like a sort of get around of the current oil sanctions on any country that's supplying oil to Cuba.

[Lily Shanaher]

And the Catholic Church in the US is providing humanitarian aid, but they're making very clear that it cannot go to the government, cannot go through the government. Experts are saying it's hard to see what Trump's idea is behind this. It's undoubtedly backed and propelled by Marco Rubio, the US Secretary of State, who is a Cuban American and vehemently opposed to Castro and the Cuban government. But what is the aftermath going to be? Cubans traditionally enjoyed privileges for immigration to the US And Trump has severed that now as well. So they're going to see something similar to the mariel boatlift of 1980, when Castro let people leave and Cubans fled en masse to Florida. The strait is only 90 miles away. They're going to see that if.

[Venetia Rainey]

Yeah, that's how the regime sort of releases pressure almost right when things get really bad at home.

[Lily Shanaher]

So if you want to go, you

[Venetia Rainey]

can go to America.

[Lily Shanaher]

And one of Trump's only policies that has been somewhat popular is the immigration policy. If he receives an influx of Cuban migrants that are currently the second highest number of immigrants arriving to the US after Mexico, a massive exodus of Cubans is not going to help the US in any way and it's just going to leave them stranded in Mexico. In terms of the humanitarian crisis in Cuba at the moment, it is devastating. As I said before, the UN has warned of a humanitarian collapse. There are blackouts even in Havana of 24 hours a day in some places, such as cienfuegos, up to 60 hours a day, which means that you can't cook, hospitals have to close, some hotels have had to close and redirect tourists. The fuel on the island. I've seen reports of as much as $10 a litre for fuel. And so everything is shutting down. Cuban economy has suffered across agriculture, fuel, medicine in the last decades and it's very hard for it to be self. And nowadays there are shortages of. I'm sure you've seen the photos of rubbish piling up that's going to cause outbreaks of disease that people are worrying about hospitals shutting down, people aren't going to be able to get treatment. It's at total breaking point. And whether you agree with the government or not, it's very hard to argue for the treatment of the Cuban people, especially in a country where dissent is so repressed. The other question is that most experts say if the US government wants there to be a mass uprising at a point of desperation, it's not when uprisings happen. So it's very unlikely that there is going to be regime change.

[Venetia Rainey]

What's your sense of how long the Cuban regime can hold on for? It's been through lots of crises before. This is an existential question for them in many ways. How stubborn is this regime?

[Lily Shanaher]

It's a very stubborn regime and the official sentiment is that it will not fall. I think a lot of people have compared it to Venezuela, but the reality is the two are very, very different. This is 80 years of entrenched ideological sentiment in Cuba and it's not a kind of for profit machine. There's corruption for sure, and there are people that are benefiting and wealthier. But whereas Venezuela was a largely self serving dictatorship with A chain of command. Cuba is not run in the same way. The people that are within the government publicly do really believe in the message, the socialist message and also the fact of the politics between the US And Cuba mean that they, even if they're not pro government, a lot of Cubans are anti imperialism and they are anti what the US Is doing. Compare that with Cubans that have left and who are largely concentrated in Miami, who are fervently largely pro maga and anti the Cuban regime. It's a very political situation, which is why I believe that it is going to try its best to withstand this. Miguel Diaz Canel has said that he's open to communication, but he said it, quote, without pressure from the US Government.

[Venetia Rainey]

Are there comparisons we can draw here to Iran, also a country heavily sanctioned, America's trying to pressure heavily, but a regime that is, as you say, entrenched and has a lot of true believers in it and would resist America's influence above all else.

[Lily Shanaher]

I remember there were reports that the Ayatollah Khomeini was fleeing to Russia and a lot of Iran experts were saying that's just not true because the ayatollah has ideological belief in this. He's not doing this for money or luxury necessarily. They really do believe in the message. And that speaks to a level of defiance. That means it's not like Assad. They're not just going to up and leave when the time gets tough. The trouble is with Iran, as with Cuba, is that messaging on both sides is highly political and it's very hard to cut to the actual truth. There have been a lot of reports, for example, of the US Trying to sniff out turncoats in the Cuban government. However, whether that's true or that's the US Trying to signal that there are weaknesses within the government, it's very hard to get to the truth about what is actually happening and what is the likely future because both sides are completely mired in propaganda, I would say.

[Venetia Rainey]

Lily Shanaher, foreign reporter, thanks for joining us on Battle lines.

[Lily Shanaher]

Thank you for having me.

[Venetia Rainey]

Right, we're going to take a short pause now. Coming up after the break, Trump's outspoken former security adviser, John Bolton on regime change in Venezuela, Cuba and Iran.

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[Venetia Rainey]

Welcome back. Now Cuba is an age old country conundrum for America. At the height of the Cold War, during the Cuban Missile Crisis, the island hosted Russian nuclear weapons just 90 miles from Florida. And over the decades, hundreds of thousands of Cuban immigrants have fled to the US now every president has approached the problem of Cuba differently, from Eisenhower's attempted invasion, the Bay of Pigs, to Obama's attempted rapprochement. To understand Trump's approach and where it might lead us this year, you can look to his first term. And who better to talk us through that than his former national Security Advisor, John Bolton. Working with Trump in 2018 and 2019, Ambassador Bolton was a strong advocate for regime change in Cuba, Venezuela, Iran, and many other traditional enemies of the United States. Since then, he has been a vocal critic of Trump and has written a memoir about his time in the White House called In the Room Where It Happened. Here's our conversation. While you were Trump's national security adviser in his first term, you described Cuba as part of a troika of tyranny. You introduced new sanctions. You ended the Obama era friendlier approach. It was clear that you would have liked to see regime change. Do you think we might be on the cusp of seeing it now?

[John Bolton]

I do think we're very close. I think the Cuban economy, as is typical, but even more so is in the tank at the moment. Cutting off oil supplies has made it very, very difficult for the Cuban economy to continue. I think there's widespread discontent on the island with the regime. The only thing that really has saved it is the continuing migration away from Cuba, people trying to get to the United States or elsewhere. But with the Maduro regime in Venezuela, I'll just say sort of neutralized for the moment. It has not been replaced. But it's the oil more than anything else that Cuba needs. If we complete the job of regime change in Venezuela, which I hope we do, I think the post Castro regime in Cuba could be next.

[Venetia Rainey]

This is clearly something that you discussed with Trump during the first term, and we'll get onto sort of what's happening now in a minute. I'm wondering how much you clashed on it. Trump tweeted in September 2019 after you'd left. He said his views on Venezuela and Cuba were far stronger than those of yours and that you were holding him back. Is that a fair characterization?

[John Bolton]

This is Trump at his best. He couldn't make up his mind what he wanted to do. In Venezuela. We publicly supported regime change, but Trump had trouble keeping his attention on it. We simply didn't do enough. We worked very closely with the opposition, but we obviously didn't do enough to succeed. I think that there was enormous support among the Cuban American community to have done more against Cuba. At the same time, we certainly did make a lot of changes from what I think was the badly misguided policy of the Obama administration. But again, we didn't do enough to bring the regime down in the first term.

[Venetia Rainey]

So what do you think has changed now? Is this all down to Marco Rubio, or do you think Trump has learned his lesson from his first term?

[John Bolton]

Well, I do think Rubio is having a significant input. There's no question about it. It does show that there's at least still one person in Trump's orbit that can have a positive influence on him. But to do regime change effectively, I've written about this extensively, you have to have a plan, you have to think about it, you have to be prepared for bumps in the road, and you have to work with the opposition in the country that you hope will take over when the regime change occurs. All that's a lot of hard work. Trump doesn't specialize in hard work. He wants quick and easy one and done sorts of things. That's not very often the case when you're trying to do a regime change operation.

[Venetia Rainey]

Is that possible in Cuba? There is no proper Opposition. What does the plan B look like for a place like Cuba where you've had a single party state in place for decades?

[John Bolton]

Well, I think that the interim would be some kind of caretaker government that continues to collect the trash and so on. But the whole condition of the island is very run down. Everything from its communication systems to its water systems all need massive upgrading and repair. And one difference between Cuba and every other potential regime change country is that there are millions of Cuban Americans and Cuban exiles 90 miles away. They have relatives, they have friends. This is going to be the quickest rebuilding, the quickest recreation of a government that anybody has ever seen. The numbers of tourists who would go to Cuba just to see it. After all these years, you can count me as one of their number. I'd be on the first plane I could get. That makes it very different from distant Iraq or even Venezuela.

[Venetia Rainey]

I wonder if you could just give us the bigger picture. I'm speaking to you here from the uk. We've got a lot of listeners around the world, Europe, Australia. You famously gave a speech in the early noughties adding Cuba as well as Libya and Syria to George. But Axis of Evil list, you said. Beyond the Axis of Evil was the title of your speech. Can you just explain beyond the sort of ideological opposition which we saw during the Cold War of a communist versus democratic country like America, why do you think this small poor island is a threat to the us?

[John Bolton]

Well in those days and still today it was engaged in trying to subvert other governments in Latin America to get regimes that were more friendly to it, like the Ortega regime in Nicaragua, which is the third in the troika of tyranny in the Western Hemisphere. We had evidence I describ described in a speech and testimony to Congress about Cuban research into biological weapons. And I think that the risk that it poses today as an example, potentially hosting Chinese espionage stations in Cuba. It's this ability of countries outside the Western hemisphere to exploit Cuba for their own purposes. Venezuela, that's what gives new vitality to the Monroe Doctrine. Remember, it's not about American dominance in the Western hemisphere. It's keeping meddlesome foreigners out.

[Venetia Rainey]

How strong do you think those links are between Cuba and China and Russia?

[John Bolton]

China in particular would like to make them stronger. I think China's been extremely disappointed by what looks to be a sort of slow moving regime change in Venezuela. Venezuela has the largest oil reserves of any country in the world. Bigger than Saudi Arabia, bigger than the United States. Until the overthrow of Maduro. Not the regime itself, but until Then China was purchasing about 75 to 80% of Venezuela's total oil exports. That was not a high number because of the decrepit state of Venezuela's oil infrastructure, but China clearly would have a lot of capital to put in there. One of the notions of the troika of tyranny was these were three decrepit regimes kind of leaning on one another for support. And if one of them fell, particularly the biggest, Venezuela, it would increase the likelihood the other two would fall. So from China's perspective, what's happening in Venezuela could have a very, very detrimental effect on their position in Cuba as well.

[Venetia Rainey]

You've mentioned several times there that you don't think Trump has effectively removed Venezuela's regime, just its head, Nicolas Maduro. But Darcy Rodriguez, the Deputy prime minister, is still in charge. You've spoken about how you think that sends a bad signal to Russia and China. Can you just explain that point?

[John Bolton]

Well, if Russia, China, other adversaries in rogue states, thinks that all Trump is really interested in finding somebody he can deal with, boy, I tell you, they'll find deals for him to do. The Russians, I think, are trying to do that, but unfortunately with some success in the Ukraine negotiations. They're saying to Trump, who cares about Ukraine? We've offered, according to press reports, to Steve Witkoff, $17 trillion of investment opportunities in Russia. That's the kind of number Trump likes. Now, the fact that the total Russian economy last year was only about 2.5 trillion countrywide may tend to cast some doubt on that number, but the point is, that's what they're offering. We see reports in the press today that Iran is offering untold investment opportunities inside Iran. Next we'll have Kim Jong Un from North Korea doing the same. If all Trump wants is a strong man to deal with, these are people who know how to do that for him.

[Venetia Rainey]

What do you think of the sort of argument that the operation in Venezuela was actually perfect, it was bloodless for America. They decapitated the head of the snake. The country hasn't been tipped into civil war, hasn't sort of triggered widespread regional instability. And some have suggested that that could be a blueprint for Cuba or indeed Iran, which we think can get onto maybe a bit later.

[John Bolton]

Well, I'll tell you one thing you can say about authoritarianism. It's stable. Boy, it is really stable. If that's what you want, great. I mean, the fact is, Delsey Rodriguez has been a Chavista her entire adult political life. She's as much of a Chavista Hugo Chavez follower who put the regime in place, that Maduro took over as any of the rest of them. And maybe most importantly of all, she's a figurehead now. Whether she remains a figurehead, we'll see. But the people with the guns, Defense Minister Vladimir Padrino, and the fellow who runs the police and the motorcycle gangs of thugs called colectivos, a fellow named d' Estado Cabela, is also still in power. What does Delsey have? Her brother is the speaker of the Venezuelan parliament. Compared to the guys with the guns, who do you think holds the real power in Venezuela? Are they worried about their current situation? Of course they are. The capture of Maduro was a brilliant military maneuver. I mean, if it didn't worry the Ayatollah Khamenei in Iran and Kim Jong Un in North Korea, I don't know what will. But it did not accomplish regime change. The democratic opposition, which won the 2024 presidential election, international observers said they got 70% of the vote against Maduro before he stole it, has been kicked to the curb. Meaning that you're doing business with what Trump, in his State of the Union message, called our new friend and partner, Venezuela. You're dealing with the thugs and authoritarians of which Maduro was only one. That cannot be a long term formula for success.

[Venetia Rainey]

So what more do you think Trump should be doing?

[John Bolton]

Well, I think it's still possible to remove the remainder of the regime. I think he should be working with the opposition, Edmundo Gonzalez, who won the presidential election, Maria Corinna Machado, who's the real leader of the opposition, to figure out how to put them in place to run the country as soon as possible. And the only negotiation we should be doing with Delsey and the rest of them is what they want for lunch on the plane that's going to take them into exile in Havana.

[Venetia Rainey]

Do you see that sort of precision military action as a possible option that Trump will be being presented with for Cuba?

[John Bolton]

Well, it is possible. I mean, this was an extraordinarily complicated effort. Again, as we saw in the State of the Union message when Trump presented this extraordinarily brave helicopter pilot with the Congressional Medal of Honor, it could have gone wrong at any number of points. So, you know, you can't count on that kind of success every time. But it does show that when things go right, the capabilities that we have ought to make every dictator, adversary of the United States worry about where they're sleeping tonight.

[Venetia Rainey]

What other military options might Trump be considering when it comes to Cuba? Or do you think he will continue to go for the economic squeeze and just wait to see what happens?

[John Bolton]

I think given that he's also now preoccupied with Iran, I think that it's economic and political pressure that we'll see on Cuba. There's a temptation in Europe and Canada and places like that to rush humanitarian supplies to the people of Cuba. Let me just say nothing goes into that island that the government doesn't control. And their humanitarian urges go to the government first and its supporters. I think the, the Cuban American community is in close touch with people all across the island. We should obviously be working closely with them. The desire of the people to be free of this regime, I think is clear. But they're oppressed by it and they know it's brutal. They know what they do to people when they're arrested and get put in Cuban prisons. So we need to cooperate with the opposition. That takes planning and it doesn't necessarily mean it happens overnight. But I think it can happen very quickly, particularly if we finish the job in Venezuela.

[Venetia Rainey]

Do you think the Cuban people would welcome a military style intervention to topple Miguel Diaz Canel and his regime?

[John Bolton]

Well, I think what they'd like to see is the regime gone as quickly as possible. I don't know that there's a military operation in the offing, but the opposition people inside Cuba itself may well have something to say in that regard.

[Venetia Rainey]

Okay, well, let's talk about whether maybe a military operation in the offing, and that's around Iran, where we've now got the biggest military build up up in Middle east region since the Iraq war in 2003. Where do you see this going? Trump's words seem to suggest that he's hesitant, but the military buildup suggests otherwise.

[John Bolton]

Well, I think the military buildup is to give him the fullest range of options. But I will say anybody who thinks there's a careful plan here, that this is deep three dimensional strategy, just think again. I've seen Trump order military operations and then call them off after they've already started and then tweet about it the next day about how he called it off just so our adversaries know what actually happened. And I don't think he knows what he wants to do. I don't think he knows what his objectives are. He wants a deal. That's the only thing Trump understands. Can't we get a deal here in Geneva today? They're having conversations. I think it's a waste of oxygen myself. But Trump, eternally optimistic for the deal is going to wait and see what happens. I think Trump should use force for several reasons. I have long favored regime change. I think this is the moment to go for it in Iran. I think the regime has never been weaker since it took power in 1979. But at an absolute minimum, Trump drew a red line for the ayatollahs during the demonstrations against the regime in December and January. Said to the people, keep demonstrating, take control of your institutions. Help is on its way. Told the ayatollahs not to execute the demonstrators. They ignored him. They killed. He said, in the State of the Union, 32,000 Iranians. Where's the help? It's not on its way. He has to use military force to vindicate the red line that he drew or see his credibility shredded.

[Venetia Rainey]

I'm curious, given you're someone who does give thought to the day after plan for something like regime change in Iran. It's really tricky. And I think the possibility of a widespread civil war in a country that big, of more than 90 million people right at the heart of the Middle east and Asia, the consequences could be enormous.

[John Bolton]

Yeah, well, how about the consequences of a nuclear capable state, sponsor of terrorism that tries to assassinate people around the world? A regime that needs to go to the ash heap of history. There will never be peace and stability in the Middle east while this regime remains in power. Its reach has been severely constrained since the Hamas October 7, 2023 attack on Israel. Its nuclear capabilities have been badly wounded. Its infrastructure for ballistic missiles and other weapons has been devastated by the Israelis. The people are opposed to the regime in overwhelming numbers for economic reasons. The young people are opposed to the regime. Women are opposed to. Opposed to the regime. After the murder almost three years ago of Masi Amini, the young Kurdish woman who refused to obey the orders to wear the hijab. Ethnic groups are dissatisfied. I think the regime can be pulled apart at the top. I hope that's what the opposition is working on. And here again, I hope Trump and the administration are working with the opposition because they are the ones that can give us the clues about timing and steps to take. But. But certainly targets. If he does want to go, I would go after the Revolutionary Guard, the Quds Force and the Basiji militia. Go after the instruments of state power that threaten us, threaten Israel, threaten the Gulf Arabs and threaten the people of Iran itself.

[Venetia Rainey]

How much of a tussle do you think there is going on in the Trump administration at the moment over those sort of dueling ideas of going in aggressively against Iran? And as you say, there are A lot of people who think that the Iranian regime is weaker now that than it's ever been and this is the right time to strike versus the more isolationist, you know, J.D. vance Strand, let's not get involved in more foreign policy adventures.

[John Bolton]

Well, I think there is a debate going on. I don't have any doubt about that. But the biggest turmoil is inside Trump's brain. It's all just rolling around day after day after day. He doesn't know what he's going to do. He hasn't made up his mind. As I say, he's hoping for a deal. And it's, in a sense, like watching a roulette wheel. We'll know what it is when it happens.

[Venetia Rainey]

On that point, I'm wondering how much you think, just returning to the Central and South America thing, how much you think Marco Rubio is pulling the strings here. Maybe that's an unkind way to put it, but I know you've spoken repeatedly about Trump not having very set ideas of his own.

[John Bolton]

Well, I think certainly in the Western Hemisphere, I don't think he has much opposition or others speaking with different points of view. But, you know, in both the case of Iran, the broader Middle east questions, Russia, Ukraine questions, it appears the Secretaries of state are Steve Witkoff and Jared Kushner, two people who know next to nothing about any of these issues. And I'm sure for Rubio, that at least, is extremely frustrating.

[Venetia Rainey]

What do you make of Trump's more aggressive foreign policy agenda? So far? There were fears he would be isolationist, but that hasn't really transpired. I wonder if you wish that you were serving in his administration. He's doing a lot of the things that you would have liked to do, right?

[John Bolton]

Well, I just wish I had been more persuasive in the first term. We could have gotten a lot of this garbage taken care of back then. But I think the conclusion, the appropriate conclusion to draw, and it's an important conclusion. Trump has no ideology. He does not have a national security grand strategy. He doesn't even do policy the way people normally understand that term. It's totally transactional. Every day is a new day. Every deal is a new deal. And what he does is anybody's guess, because he usually doesn't know what he wants to do until he's at the absolute last point he can make a decision.

[Venetia Rainey]

You mentioned the national security strategy there, and I just wondered. So in that document, he talks about transactional diplomacy and this sort of idea of flexible realism and. And there's a fairly explicit idea that he's not interested in regime change. I mean, that's the National Security Strategy, right?

[John Bolton]

Well, you've read the National Security Strategy. I'll bet you a pound he hasn't. He didn't read it in the first term. No reason to start now.

[Venetia Rainey]

That was John Bolton, Trump's former national security advisor. That's all for today's episode. We'll be back again on Monday. Until then, goodbye. Battle Lines is an original podcast from the Telegraph, created by David Knowles and hosted by me, Venetia Rainey and Roland Oliphant. If you appreciated this podcast, please consider following Battle Lines on your preferred podcast app. And if you have a moment, leave a review as it really helps others find the show. To stay on top of all of our news, subscribe to the Telegraph, sign up to our Dispatchers newsletter, or listen to our sister podcast Ukraine the latest. You can get in touch directly directly by emailing battlelinestelegraph.co.uk or contact us on X. You can find our handles in the show. Notes the producer is Peter Shevlin. The Executive Producer is Louisa Wells.

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