Is Cuba's Communist Regime Finally Collapsing?

Episode Fifty-Two: Is Cuba’s Communist Regime Finally Collapsing?

 Lee Smith and returning guest J. Michael Waller, Senior Analyst for Strategy at the Center for Security Policy and author of Big Intel: How the CIA and FBI Went from Cold War Heroes to Deep State Villains examine the current state of Cuba’s communist regime, the growing pressures threatening its survival, and the pivotal role the United States could play in shaping the island’s future.

Throughout the episode, Waller explores Cuba’s decades-long influence on international intelligence operations, its enduring relationship with adversarial powers, and the strategic opportunities facing the Trump administration as the regime weakens. The discussion also delves into the broader implications for U.S. national security, Cold War-era espionage networks, and what the collapse of communist rule in Havana could mean for both Cuba and the Western Hemisphere.

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Transcript

SPEAKER_01 0:02

From the brave roots of our funding, to the unstoppable force of American ingenuity, to the sacred inheritance of freedom we must protect. This is our legacy. Join investigative journalist Lee Smith on Roots, Rights, and Reason, powered by America's future.

SPEAKER_02 0:21

Hi, I'm Lee Smith. Welcome and thanks for joining us for this new episode of Roots, Rights, and Reason. This week we're discussing one of the thorniest issues in the history of U.S. foreign policy: America's relations with Cuba. Is the Trump administration on the verge of a breakthrough with our once friendly, then adversarial neighbor to our south? The history of relations between the United States and Cuba spans more than two centuries and reflects changing American strategic interests. During the 19th century, Cuba remained a colony of Spain while the United States expanded across North America. Because of Cuba's location at the entrance to the Gulf of Mexico, now the Gulf of America, many American leaders viewed the island as strategically important. As Cuban independence movements gained strength in the late 1800s, American sympathy for Cuban rebels increased. A major turning point came in 1898 with the Spanish-American War. With Spain's defeat and America's victory, Cuba became formally independent in 1902, and the United States retained significant influence, even establishing a naval base at Guantanamo Bay, which remains under U.S. control today. Throughout the first half of the 20th century, Cuba maintained close economic ties with the United States, but relations were transformed in 1959 when communist revolutionary leader, Fidel Castro, came to power. Ties with Washington deteriorated as Castro nationalized American-owned property and aligned Cuba with the Soviet Union. In 1961, the United States severed diplomatic relations and supported the failed Bay of Pigs invasion by Cuban exiles. The following year, the world came close to nuclear war during the Cuban Missile Crisis, when the Soviet Union secretly deployed nuclear missiles to Cuba. Although the crisis was resolved peacefully, hostility between Washington and Havana persisted for decades. President Barack Obama restored diplomatic relationships with Cuba with embassies reopened and travel restrictions relaxed. But in 2016 and 2017, shocking reports surfaced as American diplomats and intelligence personnel stationed in Havana experienced unexplained medical symptoms, including headaches, dizziness, hearing problems, and cognitive difficulties. The incidents became known as Havana Syndrome, and some U.S. officials believe that a sonic or microwave weapon might have been used against Americans. The controversy severely damaged relations, and President Donald Trump responded by reversing many of Obama's policies. He tightened sanctions, restricted travel, and returned Cuba to the list of state sponsors of terrorism. With Trump's return to office in 2025, he has continued a policy of pressure on the Cuban government, emphasizing sanctions, support for political dissidents, opposition to authoritarian rule, and more economic pressure. All with an eye to collapsing the communist dictatorship. Today we're speaking with J. Michael Waller, a frequent and beloved guest on Roots Rights and Reason. Mike is a senior analyst for strategy at Center for Security Policy. He is also author of the 2024 book, Big Intel: How the CIA and FBI went from Cold War Heroes to Deep State Villains.

SPEAKER_00 4:12

Well, there's a lot that's happening and a lot that's not happening. The happening part is that the regime is collapsing. The Cuban Communist Party just it's on a lifeline that's going to be dependent on American goodwill or bad will, whichever way you want to put it. I think it's going to be a different different from Venezuela simply because it's a smaller country and it's got a it doesn't have the natural resources and it's going to be highly dependent on what we do. So the future of Cuba is literally in President Trump's hands. It's literally in Marco Rubio's hands. And in Rubio's case, I can't imagine a better set of hands for it to be in. But of course, it's a terrible mess, and it's it's not going to be complicated because the Russians and the Chinese and the uh Raul Castro family won't leave this very easily.

SPEAKER_02 5:05

What I mean, what are that we know that Venezuela must be a part of this too, but I mean, but certainly since the since the end of the Soviet Union, the um the Cubans have been scrambling for money. Now, how how do they manage to hold on for so long?

SPEAKER_00 5:19

Well, they're really a low-budget operation. If you look at it, uh the whole island is a wreck. Uh whatever money that the that the regime figures have, they've mainly stashed out of the country. And that's a really good futures market for what the regime believes uh in its own future. If they're stashing money abroad, they don't have much confidence in their own future. So in this case, they've really done nothing to maintain even their their beautiful old capital city. The place has just been falling apart. So you have uh you have the the the Castro family that's really the ruling family. So we're negotiating with the so-called president of Cuba, but really he can't move unless old Raul Castro says so. This is where the indictment comes in handy. The recent indictment of Raul Castro as a as a you know for for killing the uh brothers to the rescue pilots back in the 90s. That's really important, and we can't have pity on him being a 94-year-old man because the guy has blood on his hands, you know, going back longer than any of us have been alive. So he really has to be removed from the scene in disgrace. So if the whole Castro legacy goes down in flames and there's nothing romantic or virtuous or nostalgic about it, once that happens, then I think the regime will be able to fall apart a lot easier, or at least elements of it will be, and then we can do a combination of uh seeking justice properly the way we would like to, but mostly cutting the sleazy deals that are necessary to remove any regime.

SPEAKER_02 6:51

Do you think that there are um that there are there's always a question with a collapsing regime, collapsing government? Um do you think that there are elements of this that are eager for Castor to die and they want to move on? They say, look, we uh that parts of it have not parked away enough money abroad. Like we live here, we have to deal with it, so we want this guy to go, and we're happy to open up relations uh with the Americans.

SPEAKER_00 7:17

Yeah, and that's that's true with any communist party. It was true in the Soviet Communist Party case, and so many of the others, where you have these hangers on who are just stagnating everything, and not even letting the country survive and sort of passing off the problems to the next generation to have to handle. That's a really big deal that they don't want. And to get this stubborn old coot who's been there since the 50s running the show, it's like, get out of the way already. It's not like they want to become pro-Western, uh pro-American. It's just they want him out of the way. You can see this too. Their kids live in Florida. They live across the United States. Their spouses, their siblings, their extended family all have property in Florida. They bank in the United States, they go to school in the United States, all of these things. We can be leveraging that and squeezing that to freeze everybody out and saying none of you are ever coming in here again and you're going to lose the right to your property here because we're going to freeze it because you're under sanction. Once we start leveraging those sanctions uh in a much more specific way, which has already begun in a general way, uh then we'll see some more movement.

SPEAKER_02 8:24

I want to get a sense, Mike, because you saw it. I mean, we've spoken with you before here, uh here on Roots, Rights, and Reason, uh, about what you saw during the Cold War in Latin America. So it'd be great if you can give us a sense of how, remind us how central Cuba was to the Soviet Union's war against the United States.

SPEAKER_00 8:45

It was really crucial for a number of reasons. First of all, it's right there on our border. But second, Fidel Castro, when he took power in 1959, represented a new, young, exciting face of communism. Communism really can work. It really is agrarian reform, and it's romantic and it's exciting, and oh, it's tropical now. It's not some Arctic thing from Russia, and it's not some stodgy Stalinist thing. So it was the latest new thing, and all the new lefties and a lot of the disillusioned old lefties could move to something more hopeful. And then that begets Che Guevara and all the romanticism that survives, you know, to this very day. So so people, Americans and others, would collaborate with the Cuban intelligence services the way they would not do with the Soviets or the East Germans or others. And this is where we really underestimate the Cuban services because uh you know it's a it's a poor, decrepit country, but it has a first-rate security and intelligence service. It's it's probably it ranks in the top three in the world in terms of political intelligence.

SPEAKER_02 9:53

I'd rather heard it's a huge threat to us in the United States, along with Russia and China. Um, I I think even more serious intelligence threat than the Iranians. Why how did the Cubans master that? Is that because of they they were uh taught by the you know by the Soviets, by the by the Russians before that? How did they get so good at intelligence?

SPEAKER_00 10:15

Yeah, they were taught by the uh by the Soviets and the East Germans and others in the Soviet bloc, but mainly those two, and really the only um peer equal that they have among the old Soviet bloc is the East German Stasi, which was state of the art. If you think about it, the the United States has never run uh agents in Cuba without the Cuban Secret Service turning them against us.

SPEAKER_02 10:44

Really? I had no idea that that that is fascinating. So that's a very poor record.

SPEAKER_00 10:51

Very poor, poor counterintelligence record on our side, terrible counterintelligence record on on our side, but it shows the skill with which that small country can outwit us decade after decade after decade. Now just think of it, they they've also turned not just American leftists through their Vencer Amos brigades, you know, people like Karen Bass.

SPEAKER_02 11:10

I was just about to ask about Karen Bass, the mayor of Los Angeles. Right. This is pretty this is pretty serious infiltration.

SPEAKER_00 11:18

It's very serious. And it wasn't like some youthful, stupid thing that she did when she was 20 years old. She kept on with this for decades. She became a scout for these Vensoremos brigades, finding Americans, vetting them, making sure of their loyalty and their reliability and their future potential to send them to Cuba for what down there are indoctrination and further assessment sessions so that they can ultimately be recruited by the Cuban Secret Service to act back again here in the United States against us, running political operations mostly. And and some and even terrorist support operations. So Karen Bass is just one of thousands and thousands of these returnees.

SPEAKER_02 11:58

Amazing.

SPEAKER_00 11:59

And you can see when she and let's say um uh the uh Barbara Lee uh of Oakland, California, and others, they come back and they ruin their cities, they promote uh uh division, they promote uh poverty and disrupt destruction. That's not because they're inept at governing, that's because they're trained on what to do when they govern.

SPEAKER_02 12:22

Interesting. Hold on. This is fascinating. So you think that, of course, we you know we've just seen uh the primary campaign in Los Angeles where Spencer Pratt was underscoring this was his campaign to say what a catastrophe Karen Bass has been. But and and the the common take is well, that's what you get with the left. They're incompetent and they do this, this, and that. You're saying that this is a the purposeful destruction of a major American city, and this is part of what Cuban intelligence services have trained Americans, Americans on the rise, Americans entering politics, already in politics, to do.

SPEAKER_00 12:58

Yes. Yes, leftist revolutionaries by nature are not good administrators, but they're not wrecking things because they're poor administrators. They're wrecking things based on Lenin's doctrine, which was called the worse the better. And the worse a situation becomes in a revolutionary situation, the better it becomes for the revolution.

SPEAKER_02 13:20

So what is the what is the next step in that and in that uh process, in that schematic? So the worse it becomes, then what's supposed to happen next? Presumably, well, obviously you don't let a Spencer Pratt in there, but what's supposed to happen after that? Does it turn into uh uh like the efforts of Zoran Mandani to uh uh not nationalize but socialize supermarkets, hand out food from the from this from the city government?

SPEAKER_00 13:50

Yeah. Or does it get steal private property, steal real estate from Pivot, redistribute it? This is all this is all basic Bolshevism 101. We just don't like to think of it that way because it was a bloody terrible mess more than a century ago. But it's it's really exactly what it was. You are destroying living conditions to make it the worse for the people, which means the better for the cadres, that is the loyal, often trained, but always obedient numbers of people who will bow to do and follow and execute whatever the leadership says, to reward the cadres, to empower them with property that's been taken from others, to distribute that property for political control, just what the Castros did. They took property away, then they handed it out to loyalists, and then they handed it out to those who will be able to receive the largest if they become loyal, but it's all politically directed. So this is what you see in LA, this is what you see in New York, in different but still um very, very similar means. It always varies from situation to situation. And this is how you create the political patronage system for a small revolutionary minority to wield a large degree of political power completely out of proportion to their numbers.

SPEAKER_02 15:10

Did Pratt ever make Spencer Pratt um his campaign, or he thought that this would go over people's heads or alienate them, that it was better just to stick with the obvious problems of the city rather than try to tie it to uh her ideological indoctrination?

SPEAKER_00 15:27

Aaron Powell Well, he did bring that up in his campaign. He he brought up the Venture Rainbows Brigades. We sent him a dossier of our own on her because um we're gonna be able to do that. Yes, yes. But but I did it as on an individual basis for this one because the center doesn't do things for political candidates. Uh but in this case, I'd been following Karen Bass for many years since she was a member of Congress, operating uh as a former Vencer Ramos Brigade member. So she, like Barbara Lee, like a lot of others from the California congressional delegation over the years, were actually fully recruited Cuban assets. You can't say that about someone who might have gone on one Vencer Ramos Brigade trip and then not become recruited. But you have to conclude this for people who throughout their entire political careers, since the 1970s, have been doing what the Cuban Communist Party wants 100% of the time.

SPEAKER_02 16:23

So what would the the collapse of the communist regime in Havana, what does that mean? What does it mean for American stability? What does it mean? I mean, clearly we still have the Communist Party of China, um, but it appears more dangerous the closer it is to our shores. So what would that mean? Does that cut does that cut um does that cut uh far people on the very far left communists? Does that cut them off from an important ideological source? I guess less less important financially at this point, but certainly a a crucial ideological source. Sure.

SPEAKER_00 17:00

Imagine if you've spent your entire life, you're in your 70s, let's say, you spent your entire life working to promote the Cuban Revolution, and all of a sudden it vanishes. You've wasted your whole life. What are you going to do now? You're probably going to take revenge against the system that destroyed that revolution. But you've already been doing that in the first place, which was why you were part of promoting Cuban revolutionary and subversive activity in the United States. So I would expect that these different elements, as as we're seeing today in Los Angeles, with this, there's no way to call it but but uh voter fraud with this whole vote count, which was entirely predictable. And of course, Los Angeles uses the smartmatic um uh voting machines and and counting technology. So you one can draw your own conclusions from from that. But this is a revolutionary minority that's bent on uh seizing power in large um geographic or power, large uh populous areas, seizing it and building their bases there. LA, New York, other cities across the United States, even smaller cities. And this is how they build and they expand their cadres. I mean the uh the jihadis had this the same word too. Well, Al-Qaeda means the base. So they're building their bases of support to expand their revolution. Where we can really win from this, though, is if the United States, in having its conversations with the Cuban leadership, and I would like to think this is why CIA Director Ratcliffe had that sit down in Havana, is if you want to come out of this transition intact, you Cuban Communist Party leaders, meaning not be sanctioned, meaning have a future, meaning not be indicted, meaning make sure your family can have a future for itself, we need the entire Cuban directorate of intelligence, lock, stock, and barrel, all the offices, all the personnel, all the records, all the archives, all the current operational files, fast all of the operational networks. That would be the single largest counterintelligence coup in American history. We would have all of Cuba's and really the Soviet bloc from previously operational archives where Cuba was had an involvement in.

SPEAKER_02 19:30

How shocking do you think that will be? But it totally makes sense what you're saying. But that's why Ratcliffe went down there, not just to talk about money and to say, here's what's happening, and we can have you can send the Secretary of State down there, a whole bunch of other people. But right, this is clearly what was going on. They're talking about Cuban intelligence services.

SPEAKER_00 19:48

We would like to hope, so we I don't really know if if that's the case, but I do know that.

SPEAKER_02 19:52

I like that interpretation very much. I think it totally makes sense.

SPEAKER_00 19:55

Yeah. Because just think, you'll have every single Cuban spy ever run in the United States. Since 1960. So every single one. And the way they do this, it's hereditary. So they will pick their new generations of follow-on. So you start becoming older. Uh, your your job as a as a as a spy, whether you're stealing secrets, or whether you're an agent of influence, or whether you're a revolutionary activist, your job is to propagate your networks. So you would have those networks of networks that were under Cuban control. We'd have all of that. We could do, we could wrap up a lot of them, we could arrest a lot of people, and especially where there were Cuban agents and our Cuban agents working against us abroad, we can take over those networks and make them work for us.

SPEAKER_02 20:46

Do you think that our I mean, look, a lot of people and you and I have spoken about the CIA before here on Roots Rights and Reason. But do you think that our I'm and and I I believe, I don't know, I haven't asked you about this, but I mean I think that Radcliffe is doing a terrific job. What's your sense?

SPEAKER_00 21:02

I heard he is, but there aren't any nasty leaks about him.

SPEAKER_02 21:07

So that means so that suggests that maybe he's not doing an aggressive support.

SPEAKER_00 21:14

If you're running the CIA and the CIA insiders are not leaking trash against you to the Washington Post or the New York Times, you might not be doing your job.

SPEAKER_02 21:23

Yeah, you're right. If you're not being attacked by in a David Ignatius column or something like that, it's uh you might be you might be resting on your can a little bit too much. Yeah. Do you think though it's possible that there are people, let's say the director, I mean, look, it's a good thing you showed up in Havana. Do you think that the direct the director and other people though who've been who've been who Cuba Cuba's been their job for decades? Do you think that they're equipped to do this and to to take over these to take over these networks and to really uproot what you know I mean again, even if the regime collapses, these networks still exist. And if the the ideological Influence is not live. These people have still been trained for a long time to do this. So do you think that our intelligence services are equipped to put these to uh use for American interests?

SPEAKER_00 22:14

I think we have some of the human talent for it. I wouldn't be overly impressed by most of the human talent that we have, or even to call a lot of it talent. But there are some folks in there who would be really excellent at it. I don't think we're bureaucratically equipped for it.

SPEAKER_02 22:29

I don't think we're psychologically equipped for it. Interesting. What do you mean not that?

SPEAKER_00 22:33

It's like winning the lottery. Most people aren't psychologically, and when they do, they waste everything.

SPEAKER_02 22:38

Right. They go broke. Yeah, absolutely. Right. Tragically.

SPEAKER_00 22:44

Yeah. So this is where Rubio comes in, where he's so important because he he's from that heritage, you know, he speaks the language fluently. He can even speak Cubano Spanish. And so he can speak straight to them. And he's got a wonderful network in Florida of people who support him on this and who have been working, like the Mast family in Florida, have been working on this for decades. And they're they're trustworthy people. The danger, of course, is that the Cuban regime has been penetrating the anti-communist Cuban American networks for all this time. Spying on them, turning them, uh making them counterproductive. So you need a whole you have a whole counterintelligence aspect to this where the Cuban Secret Service could be uh causing us a lot of problems within the Cuban anti-communist movement in the United States. And this is not far-fetched. If it's not just left-wingers who are working for the Cuban regime. If you look at the recent uh the case of the U.S. career ambassador Rocha, who was a Reagan conservative, he was working for the Communist Party of Cuba. He was just busted a few years ago. But but culturally, our bureaucracies don't look at counterintelligence, meaning countering foreign intelligence services, from a strategic perspective. They do a good job chasing down spies here and there and busting them, but they have a law enforcement mentality. Oh, they broke the law, let's collect evidence that meets court standards and then arrest them and throw them in prison, and now we get another record, uh, you know, another scalp to put on the wall or whatever. They don't do as much the long-term approach, because our system within the government, grade scale system, doesn't encourage this, doesn't reward it, to run long-term strategic operations like penetrating the enemy's intelligence services at the top, wrecking it from the inside. So we we've never taken over a full functioning, hostile foreign intelligence service before. So it's entirely new. But there's outside talent, to get back to your point, there's contractors who can certainly do the job. There are private companies who can certainly be set up to do the job.

SPEAKER_02 24:53

Um I I want to come back to something. When you said when you were talking about making arrests, my understanding now is because of encryption, it's much harder to make arrests of people who are of who have committed espionage, or it's much harder to um to charge people with espionage because the because the because getting the evidence is very hard, right? With the encryption, what's your sense of that?

SPEAKER_00 25:18

Yeah, getting the evidence is hard uh to stand up in court.

SPEAKER_02 25:22

I mean, harder now than it was, say, but before all this encryption.

SPEAKER_00 25:26

Right. That that's really hard. And really, do we really want the government to have that capability if they're going to be if they can break into a spy's signal chat, they can break into all of our signal chats.

unknown 25:38

Right.

SPEAKER_00 25:39

That's a danger to us, and we've seen the danger of FISA, right, the Foreign Intelligence Surveillance Act laws, and how that's been used to deceive judges, and how some judges have gone along with the deceptions in order to issue warrants to spy on American citizens for political reasons. So it's a big danger. So imagine this though. If we let's say the United States bought Cuba's intelligence service. Let whatever creeps running it make a lot of money as long as they work for us. There's a legal collection of evidence that will stand up in court because it was legally obtained through a foreign intelligence service that we now own and can be provided to uh investigators and prosecutors to stand up in court. So you could have many, many thousands of espionage and and other uh enemy foreign agent cases brought against people going back generations.

SPEAKER_02 26:42

Do you think John Radcliffe was doing that? Do you think he was bidding for uh bidding for the for the for for the Cuban Intelligence Archives? Here's a preliminary initial offer. I want you guys to think about it and think about it, what good it would be, how it would help you uh out of some jams that you're clearly in, and how it's good for your much more powerful neighbor to the north.

SPEAKER_00 27:07

Yeah. I would like to think it. I just don't know. Uh it could be, I mean, Biden's CIA director also went to on these types of trips, so I wouldn't put a whole lot of stock in this, but really, why else would CIA Director Ratcliffe go there except for to take over this intelligence service? He really has no other reason to go down to a to a country like Cuba except for that purpose. And there are deals you can cut. You know, we can if you become our intelligence asset, you are under certain American legal protections. You can say to say, the chief of the Cuban Intelligence Service. We can either sanction you and haul you off to to uh jail in the United States. We can sanction your wife and your children and your nieces and nephews and your mother and everybody else and seize your property and freeze it anywhere on earth and and and dog you and your family to every end of the earth, or you can help us out.

SPEAKER_02 28:05

Yeah. And we'll get your daughter into the University of Miami. She can be on the cheerleading squad. Yeah. Um, Mike Waller, last question. Um, do you think that the regime will collapse? If so, do you have a timeline?

SPEAKER_00 28:23

Oh, timelines are always a bad thing uh to think of. I mean, there is really no reason why the regime should not collapse this year. I think a lot of it is a question of priorities. It seems to me that Rubio is trying to calibrate which regimes collapse and how they do. And of course, he's under other centrifugal forces that he can't control in terms of timing, but really the Cuban regime can't survive without oil.

SPEAKER_02 28:51

Wow. So and and now with Venezuela out of the picture, they're in big trouble.

SPEAKER_00 28:56

Yeah. The the the different Cuban entities that were just put under American sanction can't survive without dollars.

SPEAKER_02 29:04

Wow. Mike Waller, thank you. We're gonna have you back when that regime falls. What is it now? We're uh it's it's it's early summer 2026. I hope that within within the next half year, I hope they fall, and we're gonna have you back on for that, but we'll have you on before that to talk about something else. Uh Mike Waller, thanks so much for being here with us today again on Roots, Rights, and Reason. And thanks to all of you for watching. We will see you in our next episode of Roots, Rights, and Reason.