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Gil Guerra
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Gil Guerra
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Jonah Goldberg
Welcome to the Dispatch Podcast. I'm Jonah Goldberg, sitting in for Steve Hayes. On today's roundtable, we'll discuss the nationwide blackouts in Cuba, the future of the ruling Communist Party, and whether or not Cuba is next to be in the crosshairs of the Trump administration's foreign policy. Dispatch contributor and Latin America expert Gil Guerra joins us today to discuss his in depth explainer for the Dispatch, will Cuba be the next to fall? Which you can find in this episode's show Notes. I'm also joined today by my Dispatch colleague Kevin Williamson and Dispatch contributor Megan McArdle. Let's dive in. All right, so let's jump right in, as Steve Hayes likes to say. Gil, why don't you sort of just help us out here with a level setting, bird's eye view of what the state of play is with Cuba. What are you seeing? What do you think's about to happen? You had that great piece that I referenced earlier.
Gil Guerra
Great. Thank you. And thank you for having me back on. This all began with the blackouts that started in March, but the history of the blackouts actually goes a little bit further. And you might think that given the decrepit state that Cuba is in, that blackouts have been a regular feature of Cuban life for longer than it has been. But they're actually relatively recent. Cuba's last blackout before the modern period was in 2004, and their electricity problems really started around 2020 because their electrical grid entirely runs on diesel. It's a very old system. It's a Soviet era system that in some cases was built in 1950s. Many of the components were built in the 1970s at the latest, but their problems really began in 2020 for two reasons. The COVID 19 pandemic really took out the tourism revenue that they were relying on, and the Venezuelan oil that they also relied on began to dry up as well. So this led to the first wave of rolling blackouts that occurred in 2021, where there were protests that became known as the July 11 protests. They were the most significant protests on the island that had occurred in several decades. They were brutally crushed within three days or so, but their problems continued. They had several major blackouts in 2024 through 2025 as well. And the most recent ones are significant because all of the previous blackouts in recent years have had an identifiable mechanical component or some sort of physical component. So some of them were caused by hurricanes that struck the island and disabled power plants. Some of them were due to mechanical failures of power plants. These are the first blackouts that have occurred because the system is coll under its own weight and because the fuel shortage has really put a lot of strain on the electrical system. So it only took a few months until the actual grid collapsed on its own. And the reason why the blackouts really matter for Cuba is because it impacts life on several different dimensions. So everyday Cubans use electricity or rely on electricity for food in ways that many people in other countries don't. So the way that Cubans have historically prepared themselves against food shortages is by stockpiling perishables and freezing them. So the first wave of blackouts for many Cuban families, especially ones that are not particularly wealthy, it really depleted their entire stocks of food that they had built up for months and for even years. So now that entire lifeline has been cut. Many other people use electrical heaters. They also use electricity, obviously, to power fans. Cuba is a very hot island. And so the way that the Cuban system has discouraged protest and has continued repression is basically by trying to use a socialist model of just providing people with the bare necessities and making them reliant on the state for those bare necessities. Obviously, when those bare necessities are no longer being delivered, you get more of the kind of protests that we've been seeing. So the blackouts led to what has now been protests that have eclipsed the July 11 protests in 2021. In duration, they have died down a little bit in intensity because the Cuban police have started preemptively arresting some of the organizers or some of the people participating in them. We got news on Sunday evening that the Trump administration had decided to allow a Russian tanker carrying some crude oil to actually break the block that we had on oil going to Cuba, which, according to the estimates that I've seen, should give the island about anywhere from nine to 12 days of electricity use. And even beyond then, we've seen that they do have some storage in order to keep facilities running. And they tend to redirect that specifically for use by the military and use by the government as well. But despite that, it seems that the theory the Trump administration is pursuing is one where Cuba collapses, which is a slightly different variation of the theory of how the embargo or pressure on Cuba would lead to regime change in Cuba. Historically, it's more of a different theory in some ways of that, but that seems to be where we are. And I think that there are a number of different factors that are unique to this time period and this moment in history that make it more complicated and also more volatile than U.S. cuba relations have ever been.
Jonah Goldberg
So, Kevin, I think there's a high degree of consensus on this podcast that communism is bad, so we don't have to debate that too vigorously. How do you feel about the idea of forcing. I don't want to say regime change. Right. Because there is talk about much more of a Venezuela model. Right. There's even talk about keeping the Castro families sort of hanging around kind of thing. How do you feel about forcing some kind of decapitation, lessening of Cuban sovereignty for the greater good? I think is the most generous way we can just sort of describe the motivations here is that communism is bad. Marco Rubio very much does not like communism, the next viceroy of Cuba. And at the same time, I have trouble not connecting dots with previous things the Trump administration has done. So how do you think about it?
Kevin Williamson
Well, I think the first thing we have to do here is acknowledge what a great podcasting voice Gil has. It's very intimidating and how his voice doesn't match his face. It's like listening to Rick Astley sing. You know, it's very true. I feel like I'm being Rick rolled here. It's very low, deep voice and it's kind of, you know, regular Washington looking guy. For those of you who are not seeing them, the video at home. Nothing wrong with being a regular Washington looking. No.
Jonah Goldberg
He should have like a red velvet smoking jacket on and be smoking a cigarette and having a Cuba Libre or
Kevin Williamson
something in a holder.
Jonah Goldberg
In a holder.
Gil Guerra
Yeah. Maybe I'll do that for the next appearance.
Jonah Goldberg
Please do. With a fez.
Gil Guerra
Yeah.
Kevin Williamson
And yeah, onto the more serious subject of Cuba, I sometimes wonder why it is we care so much about Cuba. I understand why we cared about it during the Cold War because it was an outpost of a hostile power that was serious. And it's no longer that. And I also think that Cuba presents the kind of traditional libertarian and paleo con Foreign policy, to the extent that libertarians and paleo cons have a foreign policy view with a big challenge, which is that economic sanctions don't really work if you're trying to change a regime. You know, economic sanctions against even a very poor country with a fairly rudimentary economy like Cuba's don't seem to do a lot of good. They certainly aren't going to be, I think, dispositive against a big and more sophisticated country like, say, Russia, although they can do a lot of damage. But they have to be part of a bigger package. And often, as in the case of Cuba, at least since the Bay of Pigs fiasco and all that, the United States hasn't been really willing to take the additional step of saying what that additional. That other piece looks like. So we have the ability to inflict a lot of suffering and discomfort and to prevent economic development to a certain extent, particularly on a country that's an island that's so close to us that way, where it's easier to kind of blockade it from resources in ordinary economic relations. My own personal view of Cuba is that I don't think it really should probably be a priority. I understand it's a priority for reasons essentially of political inertia, that it was a big priority in the 1950s and the 1960s and thereafter in the Cold War era. And so we're just sort of used to caring about Cuba in a way that maybe is no longer especially healthy, with all due respect to the Cuban Americans who care very much about the state of their home country and the people who live there. And it is a terrible crisis in a terrible place and terribly governed place, but in a neighborhood of terribly governed places? I mean, should we really care a lot more about the situation in Cuba than we do about, say, Haiti or other places that are really badly governed, where life is terrible, life is miserable, and the United States probably could play a bigger role in those places than it does. And again, you know, the Cuban reliance on imported diesel to run its electricity infrastructure is once again a reminder that it sure is nice to have a gigantic domestic energy industry, and also a reminder that we need to make investments in our power grid and refining capacity and other stuff in order to allow us to actually make use of all the oil and gas that we drag out of the ground instead of having to send it out of the country to be refined into usable petroleum products, for the most part. So, yeah, it's a mess. And I understand that Marco Rubio probably will be the viceroy of Cuba on top of his other 11 jobs. Is it 11 jobs you guys need administration now? Or 12 or 13? I can no longer keep count. He's no longer the official historian or whatever it is, the Librarian of Congress, whatever his job was.
Jonah Goldberg
He's not the archivist anymore. Yeah, yeah.
Kevin Williamson
So that's off his plate. So maybe he's got time to run Cuba. It's a mess. And I don't think it would take much for the United States to obviously knock over the government. I think that Trump will probably be more inclined to do a Delsey, as they call it now, and maybe even bring in one of the Castros or some member of the extended Castro Castro family. I understand their conversations already going in that direction, which would, you know, just continue to leave things essentially in the bad situation that's been in Cuba for a long, long time.
Jonah Goldberg
Yeah. So, Megan, I'm sure you've run into these people who will tell you that Cuba still. I mean, we can joke about Code Pink now, but, like, I've met plenty of people who are Code Pink adjacent who have told me, oh, you don't understand. Cuba is really just this fantastic alternative model healthcare. Healthcare. They have great healthcare and they subsidize the arts and you're poets in the streets and all this kind of stuff. And they said the only reason it's not more thriving is because of the embargo. And I always love this sort of inherent tension of saying that, but for the lack of more robust international trade, this communist dictatorship would be thriving. Do you agree with Kevin that we care too much about Cuba? Are you going to take that just vicious broadside against libertarian foreign policy, such as it is?
Megan McArdle
I care deeply about Cuba. Does that mean I think the United States should devote a big chunk of its foreign policy to trying to change Cuba's government? Probably not. Again, I think Kevin's basically right that that was a more understandable. It was a more understandable policy choice in two ways in the 1950s, 1960s. One is that it was the outpost of the Soviet un. They did indeed try to put missiles there in retaliation, I believe, for us putting missiles in Turkey, if my memory serves. And that was a legit thing to worry about. The other reason to dislike Cuba was that it was exporting and has become a real export industry for security. So, for example, even now, it was providing a big chunk of Venezuela's security service for Maduro. But also, you know, the Cubans were in the Congo in the 60s. Again, if memory serves, that is something to care about. But again, the Congo Is this critical to US interests? Probably not. But the third thing I think you should think about is that in, you know, 1968, the revolution was relatively new and could conceivably have been reversed. And things would have roughly gone back to where they were. Right. The Cuban exiles would have returned. There would have been a memory of capitalism still in the people. And that's not the case now. It's been a long time. And that means that should the Cuban government collapse, should the system collapse, rebuilding is going to look a lot more like Russia than it looked even like Poland. Right. Poland had 40 years between the Russians taking over and the fall of the Berlin Wall, Cuba will now have had 60 years. That's a longer time. And importantly, it is long enough for basically everyone who remembers capitalism to, to have died. And that means that it will. It is just going to be incredibly hard to put together. We could end up with a worse situation on our hands that we will be partly responsible for and we'll have to deal with. There will be floods of refugees. There will be. Right. And I think that is also something that should go into our thinking about how much we want to push Cuba into a state of collapse.
Gil Guerra
If I could speak on behalf of the Cuba hawks here and make kind of an argument. I think you both raise good points. You know, I'm not Cuban myself, but as a relatively white looking Hispanic with right of center politics, I'm often mistaken for Cuban. So I consider myself Cuba passing and have a certain kind of affinity perhaps also after my years at aei for the hawkish arguments here.
Jonah Goldberg
You could also play a young Marco Rubio in the, in the made for TV movie.
Gil Guerra
There you go. That's what I'm aiming for. You know, I'll be the voiceover at
Megan McArdle
least A lot of costume changes there.
Gil Guerra
Exactly, exactly. You know, I think the argument, the Cuba hawk case for regime change there is that Cuba's entire model since its inception, basically since 1960, has been one where it relies on an external state sponsor. And we are no longer in the Cold War. So obviously during the Cold War that was the Soviet Union, but now it's increasingly becoming countries like Russia, but especially China. CSIS has done some great research looking at the ways in which China has already positioned spy bases and different monitoring bases in Cuba. So if, say we just let this administration and this administration, we let the current regime stay in place. The only real thing that it has to trade on the international market basically is its proximity to the United States. And I also think that there's A similar case with Venezuela, where I think we tend to imagine if we have regime change or if we do anything, there's going to be waves of refugees that come out. People are going to start leaving the island, they're going to flood our borders, make that very difficult for us. But all of the most significant waves of Cuban refugees that have come out of the island have occurred during periods where we are trying to engage with them. The Mariel boat lift was during the Carter administration, when Carter was trying to engage more with Cuba. The Bolsoro crisis happened in the Clinton administration when Clinton was trying to engage more with Cuba as well. So oftentimes, the ways that we actually see refugee spikes, it tends to happen during these periods of engagement and not during periods where we're actually putting a lot of pressure on Cuba. And now in the region. Mexico has also taken a very strong interest in Cuba and has oftentimes conditioned things like cooperation with us on the border on our policy towards Cuba. So I think for those reasons, and primarily for the reason of China's role there, Cuba's historical role, as you mentioned, Megan, in fostering anti American movements also throughout the region, not only in Venezuela, but also in Nicaragua, there's always a risk, I think that as we look towards other countries that are also turning more towards the hard left in the region, whether it's Colombia or Honduras, there's always a risk that Cuba begins to also export its model there because it can use the influence it has on other countries not only to get aid for them, but also as a leverage against the United States in future negotiations. And we just continue having this problem that we've had since the 1959 revolution in perpetuity for another few decades.
Jonah Goldberg
So can I just ask, I mean, I take Megan's point. I think it's a good one about institutional cultural memory of capitalism is diminished with the existing Cuban population. At the same time, it feels like the black market is so sufficiently robust in Cuba because it has to be that there might be more muscle memory there. Maybe not for the formal rule of law type stuff.
Megan McArdle
Let me push back a little bit because Russia also had like a weird black market, right? Especially towards the end. And in fact, I think what really makes modern capitalism work, it's not just that people are trading that's important, but it's all the institutional stuff. And I think Russ Roberts tells a great story about an economist who goes to Russia after the Berlin Wall falls in the 90s. You know, there's people are doing a zillion conferences, so he organizes a conference, he pays a deposit, he does all this and then like two weeks before the conference, and I might be getting that number wrong, but he's very close to the conference, the hotel has just sold the space to someone else. And he says, like, I've got all these people coming, you can't do this. And the guy says, well, they paid me double. What are you gonna do, sue me, right? And here's the thing, is that in most American hotel chains they wouldn't do that. Not because they'd be afraid of getting sued, that would be annoying, right? But because they would understand like all the reputational reasons you don't do that. And they would also just feel ashamed. Most people don't do things like that even when there's no reputational cost. They just don't do them. And internalizing that, those norms and then understanding all of these complex, having good rule of law, but also anticipating the rule of law, right? All of that stuff takes decades to build. And that stuff is gone in Cuba to the extent that it ever had existed.
Jonah Goldberg
I'm very sympathetic to that point. I'll give you my own. When I lived in Prague, we loved this restaurant because they basically gave you a small sword and trident to eat this entire haunch of hog leg. And very hard to get into. You had to have reservations. And this is just very shortly after the fall of Blue Wall and all that or the end of communism. And if you were 10 minutes late for your reservation, they no longer honored it, which, okay, I'm fine with that. You'd be hard ass about reservations and stuff. But after 10 minutes, say you had 8 o' clock reservation. If you got there at 8:12, you'd see them putting the chairs up on the table because it just meant they didn't have to serve anybody else. They didn't give the table to another customer.
Megan McArdle
Right?
Jonah Goldberg
They just had one less table to serve that night. Cause that was sort of the internalized mindset. So I agree that where I was going to go with it though is that unlike the Soviet Union, I think you do still have a large chunk of capitalists of the heart in Florida and New Jersey and a few other places who have relatives have extended kinship networks that might be flocking back. Some of it'll be ugly, like fighting for their old family houses. But some of it will be like, I had a friend whose dad was a Cuban exile who had the record for, he was very proud of it. For from shovel into the ground to first customer of building a KFC In South Florida, he did it the fastest in, like, 38 days. And he spent his entire waking life wanting to go back to Cuba to build Kentucky Fried Chickens and other places like that in Cuba. And I think there are a lot of those people dying out, but I still think they kind of exist. And so I take your point. I just. It's an island. It's a little more manageable. I think there is an opportunity there for a better demonstration effect, but it could also go south.
Megan McArdle
Yeah, look, I think that's a real question is what is the Cuban Diaspora gonna do? Right. I come from a diaspora that was instrumental in freeing the native country from colonial rule through, like, donations to the various Fenian and other groups that overthrew the British, sort of.
Jonah Goldberg
This is stuff for another podcast.
Kevin Williamson
Please.
Megan McArdle
But what I'm saying is, like, I've
Kevin Williamson
got Michael Brendan Dougherty's phone number.
Megan McArdle
One thing that formed that diaspora was that there was a lot of discrimination here. And so you couldn't live really outside of an. You could, but it was tricky to live outside an Irish Catholic neighborhood. There wouldn't be Catholic churches. People would say things to you. My father was in the first generation of people who left the Boston Irish Catholic neighborhoods after a hundred years in Boston. The Cuban diaspora, I think, is better integrated than that. And again, like, the people who emigrated are dying. The people that we're expecting to go back are their kids and grandkids.
Jonah Goldberg
Yeah, no, that's a real issue for sure.
Megan McArdle
How likely is that? I don't know. Those people are mostly Americans. Right. Especially the third generation. Maybe some of them will romantically, but, like, most Irish Americans did not go back to the old country after home rule. They stayed in America where it was richer and more comfortable. And so, I don't know is the answer, but the flip side of that is it's really close. I'm sure if they opened up, hotel chains would love to build there, but I don't know how well it would go, is the answer.
Kevin Williamson
You know, I covered the opening of the first McDonald's in New Delhi, and I would love to be in Cuba for the first kfc. I think that would be a nice kind of booking for that.
Megan McArdle
Absolutely.
Kevin Williamson
You know, to your point, Megan, isn't Boston also the great example of how fast the place can change? You know, you think about it in. When John Adams is walking around in Boston, there are no Catholic churches and no masses being celebrated because it's against the law. And, you know, he's an adult in Philadelphia before he sees his First Catholic Church, and then in a matter of just a few decades, he becomes sort of the capital of Irish Catholic America in a very short period of time. Not to take us off down a rabbit hole, but just on a quick point for something, Jonah made a joke earlier about Cuba. It would thrive as a communist state if it only had more international trade. There was a time, you know, in the pre Soviet era when it was the Communists who were free trade and it was the right that was really broadly anti trade. There's this famous novel called Lord of the World. It's this crazy Catholic apocalyptic novel written and published in 1901. Pope Francis, his favorite novel, apparently. And it starts with, well, the Communists have triumphed everywhere in the world. I guess it's going to be free trade then.
Jonah Goldberg
Well, it makes sense if it's workers of the world unite. Right. I mean, there's a certain logic there.
Kevin Williamson
As a libertarian, I tell you, I felt bittersweet about that.
Jonah Goldberg
So, Gil, you're the one following this on the most granular level, the argument about Venezuela, which we had you on to talk about before. Right. I would argue that there was a lot of pretext to it. It really wasn't about fentanyl. Right. It really wasn't even about the drug war. And it turned out it wasn't even about serving a warrant or regime change. It was about getting the oil. At least that's how it seems now, since with the Delsey Rodriguez model. And I know defenders will make the case that the transition to democracy is coming and they're being very realistic about it, that's fine. We can put that aside. But there were at least serviceable pretexts to the legality of that operation, the Iran one. You had Trump saying the quiet part out loud over the weekend on Friday, saying, I don't call this war a war because if I call it a war, I need permission. So I call it a military operation. And in which case he thinks he's being super clever. But there was an argument about imminence. There was an argument about. Which I agree with to a certain. Not the imminence part, but the 47 years of Iran committing terrorism against the United States. In the debates about when Trump says Cuba is next, what is the legal team's. What argument are they preparing to justify Cuba is next as a military endeavor? Right. I mean, like, is it an extension of the argument that we're already sort of essentially doing, you know, blockades are an act of war? So in some sense we're already in the mix with Cuba and have been for a long time. But is there a legal argument for it, or is that becoming even less and less of a concern for the White House?
Gil Guerra
I think you've hit on something that's very insightful in that I think that the strategy here is very different, and the conditions here are also very different from Venezuela and from Iran. As you already pointed out and already covered, the plan seems to be to push Cuba towards some state of collapse or some state of an internal conflict that we will then have a justification for intervening on behalf of. One of the ways I haven't really seen this covered in media yet is what happens when Raul Castro dies. Right now, we are negotiating with one of his grandsons, and that seems to be the way that we are treating. The real power in Cuba at the moment is still through the Castro family. But Raul Castro is 92. He's basically the last vestige of that original revolution. And I think that there's a real question of who the actual power source is once he dies, especially if he dies sometime in the next few months, perhaps because the Cuban medical system has been degraded due to a lack of electricity. I imagine that there are several generals or military figures who will not want the power center to essentially be redirected to other Castro grandsons, many of whom have this image both within and outside of Cuba, as being kind of foppish playboys who have been perhaps corrupted by more of a Western lifestyle. I don't think that necessarily is true. I think a lot of them are still actually ideologically tied to the Cuban regime. But I think the conditions within Cuba because of the blackouts, potentially, if there are mass protests, for example, one of the things we seem to be goading them into is trying to crack down on protests. So we can frame it as sort of a humanitarian intervention if, say, people due to the blackouts, due to food shortages, due to our own kind of pushing, sort of taking the streets, and then Cuba cracks down in a way that is visible, that is easily documented, that causes outrage here in the United States. I think that's something that we saw a little bit of in Iran. Obviously, the circumstances in Iran with the protests were different, but that is why the protests so far have been allowed to continue without the kind of visible mass repression that we have. So I really think it'll be something of that nature that is still me giving the Trump administration credit for having some sort of a pre tax. It's entirely possible that there is not a pretext. In particular, I think that this. You could look at it even more cynically and say that this matters quite, quite a lot for Marco Rubio, because I think everyone can tell that there's this sort of cold war between him and J.D. vance for the 2028 nomination. I think Rubio will be tied to what happens in Venezuela to some degree. He will be tied to a lesser degree to what happens in Iran. But if you're Marco Rubio and your entire start is in Cuban exile, South Florida Republican politics, and you bungle Cuba and you let the Cuban regime go, or something bad happens in Cuba that makes the situation even worse, that would really tank Marco Rubio's chances, I think, whether or not he's on the ticket in 2028, if he ever wants a future in Florida politics, if he ever wants to continue an electoral political career after this administration, a lot of his political fate, I think, really relies on what happens in Cuba. So I think for that reason also, that creates a pressure that the Cubans understand, our foreign adversaries understand as they try to make sure the United States doesn't actually have the leverage over Cuba that it wants. That's part of the reason, I think, why Russia is delivering right now oil to Cuba and going around the embargo that we imposed. But I think that's another major factor here that will determine whether or not we actually take any kind of military action in Cuba.
Kevin Williamson
A bunch of foppish playboys corrupted by libertine lifestyles. I wonder how Donald Trump would ever relate to such people.
Jonah Goldberg
All right, we're going to take a quick break, but we'll be back soon with more from the Dispatch podcast.
Megan McArdle
Tax act understands you haven't memorized the tax code.
Gil Guerra
That's why TaxAct has live experts to help.
Megan McArdle
TaxAct can even do it for you, if you prefer. It's the easiest way to know you're doing it right. Well, other than going back to college and obtaining a bachelor's degree in accounting with a minor in finance, then interning somewhere and becoming fluent in all tax forms. But that might be hard to accomplish before tax day, so maybe just stick with TaxAct.
Gil Guerra
TaxAct.
Megan McArdle
Let's get them over with.
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Jonah Goldberg
And we're back. You're listening to the Dispatch Podcast. Let's jump back in. It's to make it just pops in my head listening to Gil the other day my friend Abe Greenwald a commentary had a interesting newsletter about the state of the Iran war, which we don't have to get too in the weeds on. But but part of his argument was the only way you're going to persuade the public that the Iran war was worth it is through victory, through something that looks like success because they don't like it now they weren't bought in. Some people have Trump Derangement Syndrome and his telling and all this kind of stuff. I think that Trump derangement syndrome stuff is overdone when it comes to the Iran war, if not about everything else too. But one of my objections to the argument was the assumption that there are. There aren't people. The implied assumption that there aren't people for whom the last thing they want is for the Iran war to be successful. And I feel similarly about. I mean, we just saw these code pink warriors going to Cuba, this delegation, which. There's a really wonderful old tradition in American politics of smug, rich white people going to communist countries to talk about how awesome they are.
Megan McArdle
The classic of the genre is of course, when PJ o' Rourke took a cruise sponsored by, I believe the Nation, to Russia in 1984. And if you have not read his essay on this, it is fantastic. And I think the best line in it was, these were people who thought everything in the Soviet Union was wonderful and also brought their own toilet paper.
Jonah Goldberg
Yes. I'd say classic of the genre. And we should be saying, be clear that P.J. was not as smug.
Megan McArdle
No, no, no. Yes. P.J. was commenting on them.
Jonah Goldberg
He was embedded among the smug. Yeah, but it goes back to Lincoln Steffens. I've been over to the future and it works. John Reed, you know, Henry Wallace. You can go out a long list these people, the last thing they want is to see KFCs and McDonald's and Cuba. Right.
Megan McArdle
It would spoil all of those beautiful vintage 1950s automobiles.
Jonah Goldberg
That's right. That's right.
Megan McArdle
And the houses that have not been touched. The pre Castro era. No updates, no repairs, no changing the facade.
Jonah Goldberg
The historic preservationists would be very upset by all of this. But on the one hand, I don't want to overstate it because I think that the crew that went down to Cuba is something of a vestige of a sort of a Cold War era kind of subculture. On the other hand, that crowd has disproportionate influence in progressive politics and journalism. And I'm just wondering, how do you think the left wing base of the Democratic Party deals with the idea of not having, I mean, like as Kevin loves to point out, Bernie Sanders idea of what. Scandinavia is basically an Epcot center version of socialism. It doesn't actually exist there. But if you lose the sort of model of real, live working socialism, is it a major psychological blow to the left? Will they just tango on and find something else? Is there a big cultural impact to that? Will they lament it simply because they don't like Trump or Will they lament it because the dream will have died?
Megan McArdle
I think they will retell the story of a beautiful, successful society that was destroyed by rapacious capitalism. They will not ask themselves why it was that rapacious capitalism had the resources to destroy their beautiful pet dream, or how it managed to also destroy the Soviet Union, which is larger than America, and China, which is larger than America and had more people. But that is how they will retell it. They will be very angry. They will not revise their priors. They just. No one people do. I don't want to say that there are lots of people who revise their priors about the workability of socialism after the fall of the Soviet Union, but the people who are digging in and really believe that. So I'm going to draw a slight parallel, which is here in D.C. we have a democratic socialist running for mayor. And people like Matt Iglesias and me were worried about this because she doesn't seem to be grappling with the fiscal realities of what. Yeah, of a city that is struggling, that has, like, lost federal jobs, has been suffering from remote work. And people keep coming back to me and Matt Iglesias, who has said some similar things and saying they're just afraid it'll work. Like, no, I live here. I don't want you to wreck. It's not. I am really not afraid this will work. If you can make it work, great, because that will be good for my property values and make my life more pleasant as a resident of D.C. but you're not going to make it work because we don't have any money. And that is the attitude that people take about basically everyone outside the 7%, most progressive people in the country, towards Cuba, which is, this obviously doesn't work. Obviously, socialism is not working. We can argue about whether, you know, the Nordic welfare states are socialism or something else. The Nordics themselves say it's something else, but that's okay. But that is the story they're gonna tell themselves is that, like, capitalism was so terrified that this was gonna work that it swept in and destroyed it just before the 60 years we put in to get to the point where it was really just on the edge of working. Socialism at this point is sort of like a joke I once heard a comedian tell where he says, you know, there's this blues musician. I've got all 13 of his albums. As far as I can tell, he's having some trouble with his woman. And I keep buying each new album thinking, this is going to be it. This is going to be the one where it works out. And nope, he's still having some trouble with his woman. And that's where we are with socialism now. But that doesn't mean anyone's going to revise their views.
Kevin Williamson
You know, there is this long tradition of lefty tourism at these places, as Jonah alluded to, you know, sort of Walter Duranty School of Journalism. But when I see Hasan Piker, who, by the way, what a great last name for this person. Piker, absolutely. When I see him swanning around these five star hotels in Havana, I see Tucker Carlson in Moscow, you know, just going on a state propaganda tour. It's not essentially just a left wing thing. It's once you've decided that you know who your enemies are, and then you can go wherever in the world and find out whatever's wrong there and tell yourself a story about how whatever's wrong there is the fault of your enemy.
Jonah Goldberg
Gil, I know you're more of a straight up Latin America expert and do a lot of stuff with immigration and whatnot, but one of the things that I've always been sort of fascinated by was part of the left's fascination with Cuba was this imagined notion that because it was Marxist, it wasn't racist. Right, because it was Marxist, it was enlightened in all sorts of ways. And for a long time, if you looked at the leadership of Cuba, it was all ethnic Spanish, white dudes running everything, and the mixed race and the black Cubans were not exactly foremost in the pictures. And as Kevin and I have talked about in the past, people also forget that when Franco died, Fidel Castro declared a week of mourning because he was so close and so fond of Franco, who the left is convinced is, you know, a minor demon in the demonology of the world. Anyway, it feels now when I watch tv that a lot of the white people have left. And I'm not sure that it matters in any significant way, but I'm just curious about it. The inequality of Cuba is pronounced because basically if you're not a high ranking Communist official or someone with deep ties to the Communist Party, you have no money. So that's a situation where you will have sort of of almost feudal levels of everyone has serf wages except for the nobility. But does it track ethnically that way anymore? Do you know, just out of curiosity, I've always sort of been fascinated by this point because it mattered so much to other people that I sort of internalized it.
Gil Guerra
There's a great book that I reread over the weekend. It's called Hidden island by Abraham Jimenez Enoa. And he himself is an Afro Cuban. He documents the stories of everyday, you know, people who are gay, who are from sort of marginalized identities, whether it's Afro Cuban or others. In this book, it's a fairly short read as well. And just the sort of complete indignities that they suffer there and the ways in which, to your point, the way that Cuba has been portrayed both in international media, but particularly here in the United States as this paradise that has kind of evolved past racism or evolved past homophobia is just completely false and is one where actually many of those prejudices are perhaps actually stronger in Cuba. That being said, I think that there's oftentimes fundamentally a disconnect between how we see race and ethnicity in the United States versus in Latin America, including in Cuba. So, for example, in almost any country in Latin America, except for maybe some, like very rich parts of Argentina, I think I would be considered white if I went anywhere. You know, I've traveled throughout, you know, whether it's Mexico or Colombia. And I'm often kind of received as being that here in the United States I am a oppressed brown minority because of how we see racial history and because we have more of a kind of an ancestral based view where it actually matters who your family was. And so here in the United States, many of my ancestors in Mexico were indigenous. I wouldn't be seen as that in Latin America. It's really more based on how you look and also how you self identify. Oftentimes so many people in Cuba who are mixed race, I think, tend to not identify as black, perhaps because of the social stigma there. But you know, really, I think part of what also matters for your question is this question of who is left on the island at this point, who is actually still there, who has not fled during the opportunities that they have had to flee. And the answer is it's basically at this point, from 2020 to 2025, Cuba has lost over a million people. It's lost nearly 10% of its population that has gone elsewhere. The people oftentimes who are left are the people, as you mentioned, who are high ranking communist officials or they're people who are too young to travel at the time or who are too old to travel at the time, or who didn't have any relatives that they were able to actually go and rejoin, whether the United States and Mexico and Spain. You know, there are people who don't have that recent immigrant ancestry where they can't get a Spanish passport. There was a lot of Immigration from the Canary Islands to Cuba, for example. So a lot of people in Cuba recently have been trying to get Spanish passports or Portuguese passports, etc. So the population that is left, apart from being elderly, very elderly or very young, does tend to be, I would say, disproportionately people from Afro Cuban backgrounds who don't have some of those same escape valves, although that's not exclusively true.
Jonah Goldberg
All right, we should do a little rank foreign policy punditry here. Know the shorthand for this is Cuba next, right? That's the question everyone's asking. That's in the headlines. You know, all that kind of stuff. Do you guys just going around the horn, do you guys think Cuba is next no matter what, or does it depend on how Iran plays out for the Trump administration? Megan, you want to go first?
Megan McArdle
Well, I think that it does depend on how well Iran goes because he is not going to get tired of all the winning. But when the winning looks tricky, he's going to pull back would be my guess. But I don't know. What do I know?
Jonah Goldberg
Kevin?
Kevin Williamson
Yeah, I think because we know how Iran's going to go, it's going to go brilliantly because Trump never does anything that turns out to be a failure. We all know that. It's going to be the winningest winning anyone ever won. And he sees himself as an important historical figure. He's old enough to think of himself as, you know, in the context of people like Jack Kennedy and Richard Nixon and people like that. And so he's definitely going to want to be the guy who took Cuba.
Jonah Goldberg
Gil?
Gil Guerra
I think it will be regardless of what happens in Iran, because if Iran is going poorly, I think that there will be a incentive to try to have something go better in Cuba. And I think that on paper, of the three militarily occupying or changing, Cuba seems to be the easiest. It's the closest to us. It has by far the smallest population, population, by far the worst military of the three. If Iran in some capacity goes in a way that he can declare a victory or declare some sort of achievement there, then I think at that point you have captured Maduro, you have declared victory in Iran, you're sort of on a hot streak, so you might as well keep going for Cuba. And I think that as I mentioned previously, the ways that Cuba matters for Marco Rubio in particular are going to create a lot of pressure for the administration to do something significant. The real question for me is whether the Delsey model will work in Cuba. I don't think that it Will, because there's not an opposition inside the country that could possibly at any point lead in the near term, even to democratic elections where they might be in Venezuela. A lot of the hardliners in Cuba are not necessarily people even that we could identify and put in the same way that we have in Venezuela, to say nothing about the fact that the Delsey model hasn't proven to have worked in Venezuela yet either. So I think that there will be even more significant complications and I think that, that there will certainly be a real need in many cases or in many ways for more direct US Involvement in Venezuela or in Cuba even compared to Venezuela or Iran.
Jonah Goldberg
All right. And so one other question on this. The reaction from, speaking in broad terms, reaction from the left about the Iran war is fairly predictable. Reaction about the Venezuela operation, fairly predictable. The reaction about potentially doing this with Cuba, fairly predictable. The right's more interesting in that the reaction from, let's just call it the maga, right. And the broader right to the Venezuela thing was thumbs up. This is often America F. Yeah, right. The reaction to the Iran operation got that reaction from some people from the get go.
Kevin Williamson
Right.
Jonah Goldberg
Forget how it's gone for a month. The revealed preferences are the reaction to it on day one. And there were other people who said this is a disaster, this is a betrayal. This is the end of Trumpism. This is, this is that we were promised no more foreign adventures, no more forever wars, yada, yada, yada. They didn't say that after Venezuela. They didn't say that the day when the Venezuela thing was announced, but they did say it about the Iran operation. Now that that aspect of the Steve Bannon, Tucker Carlson, Megyn Kelly Craft has bought into the idea that they have to disagree with Trump on foreign policy stuff. Will we hear these kinds of this is an outrage about Cuba, a Cuba operation, or will there be regression to the mean of politically supporting Trump because it's in our own hemisphere and spheres of influence and all the rest. Any predictions? Kevin, you want to go first on this one? Sure.
Kevin Williamson
Yeah. They will get upset. The right will get upset. By the way, the reaction of the right will be interesting. Jonah says, like testicular cancer is interesting. Jonah says the reaction of the right to Cuba will be the maga, right. I hate the word to say maga, but in that the Trump people in Cuba will be the same as it was in Iran if they can tell themselves a story in which the Jews are somehow at fault because the one thing they care more about than loving Trump is hating Jews and blaming Jews for things. So I guess maybe there's a bunch of Jews who live in Florida and they'll tell themselves some story about it's not really the Cubans, it's really the Jews in Florida pulling the strings and getting all this done.
Megan McArdle
Or it is Jewish Cubans, of which there were some. Matt Iglesias, I believe is descended. I think his fam. Maybe I am wrong about this. Maybe his mother's family was Jewish and not his dad's family.
Jonah Goldberg
But, I mean, Iglesias is a strange last name for a Jewish person. We'll just put it that way.
Kevin Williamson
Well, if we can figure out a way to blame Matt Iglesias for this,
Gil Guerra
I'm all in favor.
Jonah Goldberg
Gil, do you think. What do you think, think will a toppling of the Cuban regime exacerbate the splits on the right or help unify the right?
Gil Guerra
Well, what I think is interesting is that there have only been a handful of polls that have directly compared how the MAGA base feels about Venezuela versus Iran. One of them was done by the Vandenberg Coalition that polls MAGA voters every month on how they feel about certain things. For their poll of how many MAGA voters supported Operation Absolute Resolve, which removed Maduro, it was 72%, I believe, or 74. For how many supported the operation to take out the ayatollah and Iran, it was a bit higher. It was by about 10%. It was closer to the mid to high 80s. So on paper, interestingly enough, if you're looking apart from the online right influencers that we all know, the actual base seemed to assign more importance to Iran, I think, because Iran seemed like more of an existential threat to the United States than Venezuela did. I think that Cuba will be in some ways even less important. I think that there will be a certain contingent of people who, for the sake of nostalgia or for how they grew up viewing Cuba will still see it as being symbolically important. But I think that in many ways, I expect the propaganda or the kind of spin from the Trump administration to basically be, we've liberated this beautiful Caribbean island and soon we will have, you know, the Cuba of old, where there are casinos and Americans smoking cigars and there are, you know, sort of parties going on, like things will eventually, you know, basically this serves American interests perhaps more especially more in a way that brings back some of the nostalgia that I think was especially, especially apparent in the beginning of the administration for the Gilded Age, for this age where Latin America was sort of the administration's or the United States's rather playground where people could go and have a good time and have some Cuba Libres and some rum. You know, that is not necessarily what is being portrayed in Iran as the future quite so much. But I think a lot of the interests that the Trump administration has, obviously in things like casinos and things like the tourist sector, et cetera, will color a lot of how the base views what Cuba means for them. And I don't expect that despite a lot of their antipathy about immigrant diasporas and how immigrant diasporas influence American foreign policy. It's always very curious to me how Cubans virtually never get kind of attention on this part from the part of the new right. People are never really upset about the fact that you oftentimes have to speak Spanish to go to Miami. That isn't really ever brought up. And I think that obviously anti Semitism plays a big role in for why some of those double standards are applied. But I don't really expect there to be much of a backlash, if at all. There's not going to be anyone posting memes about how they're not going to go die for Cuba, for example, the way that we were seeing oftentimes all over Twitter after the operation interrupted on
Jonah Goldberg
so I did a bit of a deep dive trying to think about what to write a column about. There's this guy running for railroad commissioner who at CPAC said that he wants to deport 100 million people. And it turns out that this is like a big talking point on the whack job, right? And lots of people said it, the former head of CBB said it that the goal should have been 100 million deportees. And when you start doing the math, you realize how, how problematic that is. But if they were to follow through on it, this could be one of the great moments in settler colonialism where we sent all of these capitalist loving Americans to Cuba to make it, you know, the 51st state or something like that. But probably not going to happen. Before we take a break, please consider becoming a member of the Dispatch. You'll unlock access to bonus podcast episodes and all of our exclusive newsletters and articles. You can sign up at the dispatch. Thedispatch.com join. That's thedispatch.com join and if you use the promo code roundtable, you'll get one month free. And speaking of ads, if they aren't your thing, you can upgrade to a premium membership. No ads, early access to all episodes, two free gift memberships to give away, exclusive town halls with the founders, and more. Okay, we'll be right back.
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Jonah Goldberg
Welcome back. Let's return to our discussion. All right, it's time to do Dispatch recommendations. This is where we ask our podcast colleagues to recommend something they've seen or heard on the Dispatch recently. And why don't we start with brother Kevin Williamson?
Kevin Williamson
Well, just to annoy Jonah, you know, Steve Hayes and I are very different kinds of writers, but we both love a freak show. And Steve's story on this congressional race down at Bonita Springs, Florida, where everyone's like, from Long island and Ohio, and they're failed Republican candidates from everywhere else. They're all sort of parachuted into this very Trumpy District. And half of them have had pardons for various things that they've been involved with. And a really, really fun piece of work. That's the sort of thing that Steve really does a good job of.
Megan McArdle
Megan, I want to pitch. I'm Jennifer Steinhauer's the Era of Cookbooks Is Not Over. Those who have followed me in other venues know that I am a deep kitchen nerd, and I have so many cookbooks that they are not only in the kitchen, they have spilled over onto mantles, onto bookshelves. And it was just a beautiful ode to something that you would think would go away in the Internet era, but I think has in many ways become more vital than ever.
Jonah Goldberg
And as someone who was fairly recently at Megan's house for a wonderful, delightful dinner and really excellent cocktails as well, I can attest that it is, as my wife said when she walked into the kitchen, you can always tell whether someone actually cooks by their kitchen. And Megan's is a wonderful kitchen for actual cooks. It's not a show kitchen. It's not a showroom kitchen.
Megan McArdle
It is definitely not a show kitchen, but we're fond of it.
Jonah Goldberg
Gil, what you got for me for
Gil Guerra
a bit of a deeper cut? There was a piece that was published in September as part of the next 250 series called our Almost Promised Land by Joe Pitts, which is about the West. I think it's a really interesting look at the way that the west historically was sort of this frontier place where you could make new beginnings, try new ideas, and the ways in which, thanks to the progression of history and globalization, now the west has lost a little bit of that. But also still is this place where people from the east can go and sort of start anew. And what starting anew means in an age where those new beginnings are increasingly hard to make. As someone who grew up in the south and the Midwest and is now very much a creature of the east coast and has never spent any time in the West, I found it a really fascinating look at what regionalism still means in the United States today.
Jonah Goldberg
All right. And I'm going to go with one on a topic that's been near and dear to my heart for a while now. We have a great it's just up. It's up today. And I probably made a terrible mistake picking it because I have to pronounce the writer's last name.
Kevin Williamson
Williamson. Not that hard, Jonah.
Jonah Goldberg
It's J. Sovolkalyan, and it's on the institutional rot of the rights youth politics. This is something that I've been worried about for a very long time. I find that the all the people who wanted the right youth movement to organize and to be self consciously a youth movement, we're storing up trouble in the future because youth politics sucks. And it doesn't just suck for the left, it sucks for the right. And we now have a really poisonous form of trolly, racist, anti semitic youth politics that is increasingly, as the author says, institutionalized. It's a good piece on it and I hope the Dispatch continues to do more on it. And with that, we're going to move to Not Worth youh Time. Melania Trump walked out recently with a robot, and when you just look at the still shot of it, it looks a bit like it's the basic promicote robot and then the one with the skin suit as they're coming out. But that was in fact not the point. You cannot yet buy a Melania Bottom. It was part of her effort to push the idea that robots can become companions for kids and that artificial intelligence can someday soon tutor our youth in art and philosophy. Is this an idea that's worth our time? Is it an idea that is unavoidable?
Gil Guerra
Megan?
Megan McArdle
It is an idea that's worth our time because we're gonna have to grapple with these problems. This turned out to be an especially prescient not worth your time because I have now spent the Weeknd being the main character on Twitter after having said that I use AI for things like, you know, finding me stuff to read. And none of the things that I mentioned were things that they were all things that writers use humans to do. Now, I have never been so privileged as to have a research assistant, but many professional columnists do, and they use the research assistant to like, go get them, like information, to download reports, to summarize things.
Kevin Williamson
Fact check.
Jonah Goldberg
True, I can attest to that.
Megan McArdle
Yeah, well, that was one of the things that people got maddest about was the fact checking. And I was inundated by people who said, but it's not good at that. And the funny thing was the people who were accusing me of outsourcing my thinking had themselves. I just started asking them, so, like, how many of the models have you used? Which ones you're using? Do you have a pro subscription? How much work have you put into your instruction set and your prompt? And they all immediately were like, no, look at this article from two years ago. And it was clear they'd outsourced their thinking to other people who told them it's a Stochastic parrot and it's useless. So I think it's a really useful tool. But the hard problem and I think the legit critique here, I've been doing this for 25 years. I have a lot of domain knowledge, I have internalized ethics, and I have a sense of where, how to use it so that it is not replacing my thinking. It is speeding real grunt work. Right. Like you can now use Claude. You just say Claude. I want you to go to the D.C. government's janky website. I don't want you to download 20 years of budget reports and then I want you to take this table.
Jonah Goldberg
But I thought you were trying to use examples of things. You use it for work and that's what you do in your free time.
Megan McArdle
Right?
Kevin Williamson
Right.
Megan McArdle
Well, I mean, look, we all gotta have have some fun too. And like, the number of people who got mad at me, for example, for saying I used it to format my podcast scripts and like, I will make a list of questions and then I will say, you know, put headings on these things and like, put numbers. Right. And people were like, this is an essential part of journalistic work. And I'm sorry, at the moment where you are telling me that, like, typing headings and choosing fonts is part of my essential work that dare not be outsourced lest I lose my core abilities, we've just now entered into ridiculous land. But the thing is, how do you get to that point? So first of all, how do you. I am an obsessive writer. I did this for free for five years before I ever got paid for it. Right. Not everyone feels that way. So some people are going to want to take shortcuts and then how do they build the skills? But also, if I don't need an intern now, I don't have an intern. I've never had an intern. But again, other people do. And if we don't need those people to do that grunt work, which is part of how they are socialized into our profession, how they learn to do things, how do we get people to the point where AI is a really useful auxiliary? I think that's a really hard question. And I think that goes directly to the question in education, which is there are ways in which I can imagine it being a really good tutorial. But if I think of kids using it as that versus kids using it to cheat, I'm looking back on my own childhood going to imagine most kids using it in the easiest way. And I will also say that in general, having good ed tech is not just about the technology. It's about how the school districts implement it. There was a guy who recently went viral on Twitter complaining about how his child had been sat down in front of this terrible he's an engineer, he's married to an engineer, and his kid hated math because it turned out that the kid was being sat in front of software where the software would read the question aloud and then he would have to wait and then he could click in a box and then he would wait and there was no way to stop the part where you have to be read to. And it was totally stupid. But Matt Iglesia is going back to that closing that letter loop came back and said my kid uses it and it seems to be fine, but his school district is using it just for assessment. And so like, while I can theorize an AI tutor that will be good at this, and I think some kids will have one, I worry that most kids will have something that makes things worse rather than better.
Gil Guerra
Gil I think Megan's spot on about using it for things that don't replace thinking. I'll just add two anecdotal examples from my time working with young people, because before I was in think tank research, I was in academic programs at the American Enterprise Institute. And one of the real drop offs that I've seen in reviewing internship applications, whether it's for the Niskanen center, whether it was for aei, whether it's for a volunteer program that I helped run for young professionals in foreign policy. The first really big decline I saw in quality of COVID letters and of interviews that I was conducting came after COVID 19, when education went online and when people started learning virtually. The second one came after what I would say was widespread adoption of ChatGPT, at which point at various times and people who I spoke to for various programs and interviewed various programs, it was very apparent to me that some of them, even the ones who made it to the interview stage, had used AI to write their cover letters. And part of the reason that I knew was that when I would ask them questions about things that were on their resumes or their cover letters, they seemed to have no idea what I was talking about because they hadn't actually written them or read them them. I've had various instances in the past year where when I'm introduced at events, the person introducing me has an AI hallucination. For example, in my bio I've been given a book I did not write. For example, I haven't read any books. I've been given a doctorate. I don't have a doctorate. I've been given the wrong undergraduate institution, et cetera. So I think that there are a lot of risks with using it to actually replace human thinking with athletes, using it to replace things that you actually need to verify and check for yourself. But I do agree with, with Megan, and I myself use Claude, for example, to do a lot of finding new sources. But, you know, the trick is you have to actually read the sources yourself.
Megan McArdle
Yeah, absolutely.
Gil Guerra
I know that's what you were saying and that's what you were saying, so I agree with you entirely there. But that's very much the way that I use it, and I agree also with Megan that I think that it requires a level of discipline. It requires a level of knowing how to do that that is much easier to do when you grew up, not really having the option to use AI beforehand. And I do worry about kids having the discipline or busy parents or busy teachers having the incentives to actually force kids to use. Use those kinds of methods instead of kids just taking the easiest way out because they don't know any better or because they haven't actually developed kind of the discipline to do that themselves.
Megan McArdle
Yeah.
Jonah Goldberg
Kevin, are you going to tutor your kids with AI? Let them learn Plato's Republic from Claude?
Kevin Williamson
Well, thank you. Jonah Goldberg, author of the Prime Ministers we never had a history of Canadian opposition leaders, at least according to Amazon.
Jonah Goldberg
For people who don't know the reference, Amazon has a long list of books that I have quote, unquote written that I've never written. And I and my agent constantly has to send them cease and desist things, but they always come back. So anyway, go on.
Kevin Williamson
So Melania is saying, imagine an AI called Plato, because of course it's going to be called Plato, teaching your kids philosophy and this sort of stuff. And if you go back to the early days of radio, you go back to the early days of television, you go back to the earliest days of the Internet. There's always the same story. There's someone out there saying this new technology is going to be able to have Americans sit at home in their living rooms and listen to the best lectures from the Philosophy of department at Harvard. And that's how they're going to spend their evenings. And in five years, people are using it for pornography because that's what actually drives technological innovation. It's like 10 years after the Gutenberg Bible is printed, there's pornography in print. AI is very likely to follow the same course. You know, it's funny with the robot thing, and you joked about Melania being the skin suit version. That's actually what will be the. That'll be the commercially successful version of the humanoid robot. Right? Because we're going to end up using them for manual labor and sexual. That's what robots are going to be used for. I guarantee you in that 50 years from now, that's what robots will be used for. The AI stuff is going to follow, I would imagine, the same path as most other technological innovations. You know, social media became a sewer, the Internet became a sewer. Radio became sort of a sewer, television became sort of a sewer. And you can really only Trust Books. Megan McArdle is dead to me for letting a machine pick out typefaces. I may be the only person in the world who still kills typefaces very much, but typefaces are, are very important.
Megan McArdle
I'm working in Google Docs. It's not like we have a lot of awesome options.
Kevin Williamson
You can install typefaces in there, I believe, but then you should work on a better document system.
Megan McArdle
But I didn't pick it.
Kevin Williamson
Anywho, typefaces kind of matter. I care about that stuff. The whole reading experience matters. A little bit of a tangent, but I think it's actually related. People often ask me, like, what news shows do you watch? And like, what should you watch to really get a good balance? And I always tell people it's not a matter of which program you pick, it's which medium you pick. And if you're watching your news instead of reading your news, you're getting garbage. And if you are going to be relying on AI for doing anything, that's beyond the sort of stuff Megan's talking about, which is pretty good at doing grunt work and sort of things that are easily automated or not easily automated, but things that are amenable to automation, even of a sophisticated kind, it's going to be useful that kind of way. I also have never had a. An assistant, so it's the one thing in life I really want other than a private jet. But I kind of think that the notion that it's going to be teaching kids the liberal arts and philosophy and classical rhetoric and things like that is not going to happen. Not because AI can't do it, because that's not what people want. And technology is driven by demand. And what people have demand for, apparently, is online gambling and rage, politics on social media and tremendous amounts of pornography in cookbooks.
Jonah Goldberg
I agree with a lot that's already been said. I will say in defense of research assistants, I was a research assistant, one of the Things that made me a great research assistant, and I will say I was a great research assistant, was that my father raised me that whenever I asked a question about anything that he didn't know the answer to, he would say, let's go look it up. And I also had I read widely and I had a good memory for where and what I read. So that by the time the Internet came, it was just a multiplier for a skill set that I'd already developed. And I think I use ChatGPT for some research stuff. I cannot tell you how many times I've screamed at it, dropped many F bombs by saying the quote you gave me here is not in the text because I checked. And every single time I say anything I want verifiable sources for everything because I'm going to go check. So it's better than Google for searching for stuff because it can constrain if you prompt it the right way to better sources for you to read yourself. And that's great. I will defend that. And I do think it's coming for the RA slots, which I think is very sad because some of those jobs are the best entry level jobs into a thinking life. And at the same time, I think the future of education is going to be for elites at least it's more likely to be like 19th century elite British education than it is like anything involving technology. You're going to have kids have to take tests in the classroom in real time because that way you can't cheat with AI. And they're going to be in environments where their access to technology is restrained or constrained for large swaths of their educational days or years precisely so that the kids can build up those muscle memories. And then the kids from less elite backgrounds will not get that. And that will fuel more societal inequality in ways that I don't think we have really thought through. But that's just me being dyspeptic. So with that, I want to thank our guests. I want to thank you all for listening. If you like what we're doing here, there are a few easy ways to support us. The easiest is you can rate, review and subscribe to the show on your podcast player of choice to help new listeners find us. You can also again subscribe to the Dispatch. And as always, if you've got questions, comments, concerns or corrections, you can email us@roundtabledispatch.com Please let them know how eager you are to have Steve come back to host this podcast. So that's going to do it for us today. Thanks so much for tuning in, and a big thank you to the folks behind the scenes who made this episode possible. Noah Hickey and Peter Bonaventure, thanks again for listening. Please join us next time.
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Episode Date: March 31, 2026
Host: Jonah Goldberg (in for Steve Hayes)
Panelists: Kevin Williamson, Megan McArdle, Gil Guerra (Dispatch contributor, Latin America expert)
Main Theme: Exploration of Cuba’s spiraling crisis—focusing on blackouts, social unraveling, and whether the Trump administration will intervene for regime change. Also, a broader debate about U.S.-Cuba policy, the legacy of communism, and what comes next.
This roundtable delivers a deep dive into Cuba's current crisis, particularly unprecedented rolling blackouts, their historical and geopolitical context, and the increasing possibility that the Trump administration will turn its “regime pressure” focus to the island. With Latin America expert Gil Guerra, the panel dissects the causes and consequences of Cuba’s energy collapse, debates the logic and risks of U.S. intervention, and discusses how different American political factions might respond if Cuba becomes the next flashpoint.
[01:59–05:50] Gil Guerra Explainer
[05:50–10:21] Kevin Williamson’s Perspective
[10:21–13:32] Megan McArdle Adds Nuance
[13:32–16:10] Gil Guerra Responds
[16:10–19:54] Robust Debate: Black Markets, Culture, and Diaspora
[24:19–27:26] How Would Trump Justify It Legally?
“The plan seems to be to push Cuba towards some state of collapse or some state of an internal conflict that we will then have a justification for intervening on behalf of.”
— Gil Guerra [24:30]
[31:48–36:45] The “Romance” of Cuban Socialism
[37:18–41:19]
“The way that Cuba has been portrayed as this paradise evolved past racism is completely false, and actually many of those prejudices are perhaps stronger in Cuba.”
— Gil Guerra [39:00]
[41:19–43:53] Foreign Policy Punditry
[43:53–48:57] How Will the Left and Right Respond?
“[In Cuba,] often you have serf wages except for the nobility, and the population left is mainly elderly, very young, or Afro-Cubans without family abroad. Cuba's reality is very different from its romanticized narrative.”
— Gil Guerra [41:00]
“We now have a really poisonous form of trolly, racist, anti-semitic youth politics that is increasingly, as the author says, institutionalized.”
— Jonah Goldberg, referencing a recent Dispatch article [54:44]
“If you're watching your news instead of reading your news, you're getting garbage. And if you are going to be relying on AI for doing anything, that's beyond the sort of stuff Megan's talking about... it's going to be useful in that kind of way. I also have never had an assistant, so it's the one thing in life I really want other than a private jet.”
— Kevin Williamson [64:32]
The conversation maintains The Dispatch's signature: intellectually sharp, irreverent, deeply informed but wry and skeptical. It mixes empirical foreign policy analysis with pop-culture riffs and pointed jokes, especially at political tropes on both left and right.
The panel concludes that Cuba is more vulnerable and exposed than at any point in decades. The Trump administration is not just maintaining pressure but taking positive steps to force a regime crisis, with political calculations (especially for figures like Marco Rubio) at the fore. Yet all agree: regime change in Cuba would be far messier and more complicated than past interventions, with risks of chaos, refugee flows, and unpredictable political fallout domestically.
For listeners seeking a thorough, witty, and historically grounded dissection of Cuba’s impending tipping point, this episode is essential.