Isaac Saul (17:45)
All right, that is it for the left and the right, and some voices from Cuba are saying. Which brings us to my take. One of the most difficult parts of political analysis is resisting the urge to create patterns out of events that are actually distinct. Amid the wide array of commentary about Cuba, a lot of otherwise smart and thoughtful political writers are making this mistake. It is in some ways irresistible. President Trump just launched prolonged military operations against Iran, a country with a repressive regime whose citizens seem fed up by the state of affairs in their country. On the surface, that sounds a lot like Cuba. In Venezuela, Trump just ambushed the regime, removed President Nicolas Maduro from power and brought him back to the United States on charges of drug trafficking, an economically devastated Spanish speaking country in the global south with an association to drug trafficking. That sounds a lot like Cuba, too. The surface similarities invite us to see a pattern of action that may not exist. So let me start with a moment of clarity. Cuba is not Venezuela. Cuba is not Iran. Cuba is not Greenland, Ukraine, Mexico, or any of the several countries Trump has had military, diplomatic and economic standoffs with so far in his second term. And it should be written about distinctly. I think it is smart and healthy to look for patterns to anticipate potential outcomes. But I do not think it is wise to assume the outcomes will be the same or create false equivalencies between Cuba and any other country. As readers of this newsletter know, I've been quite critical about some of Trump's recent military, diplomatic and economic interventions. I criticized Trump's global tariffs and eventually suspected they'd be struck down as illegal. I recognized the geopolitical value of Greenland but criticized the communicated approach of acquiring it by force or fortune. I loathe the Maduro regime but wondered about the motivations oil to upend it and the new standard of operations set in international law and in Iran. I've been more explicitly critical, questioning the justification, the outcome, the legality and the forward looking plan. Yet with Cuba, I come into this potential intervention with much less certainty on whether the risks outweigh the upside. When I look at the specific geopolitical questions at play here, I genuinely don't know how I feel, and I'm far less confident in my assessment of this issue than I was about the others. I feel torn genuinely. To start with the upside, a few things here feel distinct from the examples everyone is comparing Cuba to. First, Cuba is not only in our sphere of influence, but it's close enough just 90 miles south of the Florida Keys to be a legitimate security concern. Russia and China have been making inroads onto the island for decades, which further increases our national security interests there. Also, Cuban Americans who fled the communist regime and live in the United States appear to be broadly supportive of, if not outright giddy about, the prospect of America forcing new leadership in Cuba. Their political interests, especially given how many have family or friends still trapped in Cuba, carry some weight here. Second, Trump's increased economic pressure seems to be advancing some diplomacy. The president's pressure is not the core issue here. Cuba is in dire economic straits and has been long before Trump hit the political scene. Because it is very reliant on imports. It doesn't produce anything of value at scale, not even sugar anymore. Its dilapidated infrastructure has not been maintained, and its oppressive regime refuses to allow the proliferation of a free, free economy. For example, its updated laws include the state taking over 51% ownership of foreign joint ventures. Even in September of 2025, before our operation in Venezuela and before any oil embargo, reports of the dire situation in Cuba were everywhere. It is the peak of American obsessive criticism, often proffered by non interventionists and progressives to look at Cuba and think that we are responsible for its struggles. As one Cuban economist put it in the New York Times, what is happening in Cuba today is essentially the result of decades of structural economic failure under a rigid political system that has consistently resisted any reform. Cuba's communist leaders enjoy exorbitant wealth while their people have struggled to feed themselves for decades. If you're upset about the economic conditions there, be upset about that now, with the regime in a moment of genuine weakness. Trump can offer incentives like removing tariff threats on oil sales, opening access to Cuban markets, normalizing relations to encourage tourism, et cetera, all to drive Cuban leadership toward democratic practices and normalize relations with the United States. The talk seemed geared toward avoiding military confrontation and instead exchanging economic relief for the first free and fair elections in Cuba in over 70 years. There is a single legal political party in Cuba. Maybe they can have two. It shouldn't be crazy to dream of something as basic as that. Unlike Iran, the Cuban government seems willing to engage in good faith in meaningful negotiations. Unlike Venezuela, where a military buildup coincided with diplomatic pressure, the potential for military conflict seems less likely. Third, and importantly, the Cubans themselves seem very interested in supporting whatever it is the Trump administration is selling. Protests against their current government are reaching a fever pitch, and the frustration is not about American policies, but the decades of oppressive leadership and broken policies that have left nearly 11 million people to desperately imagine a post Castro future. To sum up the case for intervention here succinctly, the Trump administration has a compelling case to intervene in Cuba in a way that supports human rights and democratic change, protects U.S. national security and economic interests, and delivers a major political win to a distinct domestic constituency. All of that, to me, feels unique and valid. But that doesn't convince me US Intervention is a good thing, because even diplomatic intervention has plenty of risk, too. The same Cuban people who stand to gain from intervention are also most directly impacted by economic sanctions, not their exorbitantly wealthy communist rulers. Conditions on the ground in Cuba are already bleak. What if they get worse? And if economic conditions worsen, street violence escalates and the already chaotic and precarious moment in Cuba becomes disastrous. The what happens then? Economic pressure alone rarely topples authoritarian regimes. That usually requires military force, and it is often a precursor for it. Given the history of our two countries, many Cubans are understandably wary of some friendly US Takeover. And it's foolish to think US Soldiers would march through the streets of Havana to applause. A worsened economic situation could lead to a military confrontation of some kind, and one predictable outcome of that is thousands, if not hundreds of thousands of Cubans fleeing the country. And when they flee, we know where they'll go. Florida. This obviously would create just the kind of refugee crisis that the administration wants to avoid. It would also set up the horrifying and likely possibility that the administration turns away refugees had helped create. For me, this would be worst case scenario, and it feels only a few steps away, so I just don't know. On the one hand, our motivations for intervening in Cuba are more obvious, more grounded, more holistic, and more just than they have been in countries in recent months. We have a Cuban American secretary of state who has long sought this kind of change and seems well positioned to navigate it. Had this potential intervention began last year, before fresh conflicts in Iran or military operations in Venezuela, I think the Trump administration could have much more easily sold me on this as a viable and worthwhile use of our resources, political capital and economic might. On the other hand, this potential intervention is coming as a new war in Iran continues to expand and on the heels of an operation in Venezuela that does not seem to have satiated the administration's thirst for regime change. Our president isn't beating the drums of democracy. Instead, he's bragging about how easily he could simply take the country. I could do anything I want with it, he said. And as has become common, the quest seems more about his personal ambitions than the people he purports to be helping. So I come to this possibility in a moment of wariness, both of war and of the reshuffling of power. I want a better future for the Cuban people, yes, and I want our national interests off the coast of Florida to feel stable, definitely. But it's hard to be Pollyannish about the risks given the global instability in nearly every direction I look. All right, that is it for my take. We have a staff dissent today from senior editor Will K. Back, so I'm going to pass it over to him. We'll be right back after this quick break. Foreign
