Hi friend,

I have seen firsthand what the collapse of a country does to its people.

Cuba feels like it is approaching something similar. And yet the conversation around it in most media is so simplified it barely touches the actual history.

Mikael Wolfe is an Associate Professor of History at Stanford University, whose work focuses on modern Latin America and U.S.–Cuba relations. Bringing more than 35 years of scholarship and firsthand insight from two personal visits to Cuba, he joins this conversation to share his perspective.

And what he says about whose war this really is, about what a US intervention would actually look like, and about the history of Cuban democracy before Castro, is something worth hearing before the next headline appears.

The history nobody is telling you about Cuba

Most coverage of Cuba right now starts in 1959.

Mikael Wolfe starts earlier. And what he finds changes the entire framing.

The argument from Cuban-Americans and Republican politicians is that a Cuba free of Castro would be a free Cuba. That before the revolution, Cuba was moving toward democracy and the US simply wants to restore that.

Mikael challenges this directly. Cuba has never actually been a liberal democracy. Spanish colonialism was not free. US military occupation after the Spanish-American War was not free. The governments before Castro were not free. The 1940s offered a brief democratic opening, but it was so corrupt it could not govern effectively. Batista overthrew it in 1952 through a military coup.

Here is the detail most people do not know. A young Fidel Castro was planning to run for office electorally in 1952. That option was blocked by Batista's coup and armed struggle became the only remaining path.

None of this is to defend what followed. Mikael has his critiques of Castro and says so directly. But the historical record matters because it tells you what a US intervention is actually fighting for.

The more urgent question right now is who is driving this. Mikael's answer is specific. If there is a war in Cuba, it would be Rubio's war more than Trump's. And prediction markets are putting the probability of military intervention by June at 25%.

Mikael says it would more likely fail than the operation in Venezuela. The reason why is in the full episode.

In this episode you will discover:

Notice when a narrative skips the history

Mikael's most important point was simple. The story most people tell about Cuba skips the parts that complicate the conclusion. Cuba was never a liberal democracy before Castro. That fact is not in most news coverage because it changes what the intervention is actually about.

This week, when you encounter a strong political claim, ask one question before accepting it. What part of the history is this leaving out.

Why: Most narratives are selective by design. The part that gets left out is usually the part that matters most.

How many conspiracy theories have actually turned out to be true?

History shows that some have.

In this conversation we go deeper into the real issue. How do you stay open-minded without believing everything? And at what point does a claim actually meet the burden of proof?

History does not repeat itself, but it rhymes.

Mikael spent this conversation showing exactly how. The same resentments, the same strategic interests, the same political calculations that have shaped US-Cuba policy for 65 years are shaping it again right now.

The question is whether anyone in power is actually reading the history.

Know the history before the headline.
Julian x

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