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Who’s Ready to Invade Cuba?!

A story about communism, “regime compliance,” and oil.

Jonathan V. Last's avatar
Jonathan V. Last
Mar 31, 2026
∙ Paid
A tugboat guides the Russian oil tanker Anatoly Kolodkin as it arrives at the oil terminal in the port of Matanzas, northwestern Cuba, on March 31, 2026. (Photo by Yamil LAGE / AFP via Getty Images)

1. Cuba No Libre

Today a Russian oil tanker docked in Cuba. It was the first oil delivery to the island since January 9. The worst-kept secret in the world is that the Trump administration is working to topple the Cuban government.

The administration has been playing a very long game with Cuba. The entire Venezuelan project—the obsession with Tren de Aragua, the lawless attacks on boats off the Venezuelan coast, the abduction of Nicolás Maduro—only really makes sense when viewed as the first half of a plan to liberate Cuba.

And right now, Cuba is in trouble. The American sanctions have crippled the country’s economy. The Communist regime is struggling to survive, but the walls are closing in.

Maybe the regime in Cuba falls on its own; maybe Trump gives it a push. Either way, this is Trump’s next foreign project. So let’s take a minute and get smart about what’s happening in Cuba and what regime change there will mean for America in the coming weeks or months.

Warning: This stuff isn’t sexy. There won’t be a lot of ‘splosions and Maximum Lethality. It’s a story about economics and authoritarianism. Most of all, it’s a story about oil.

And it’s complicated, too. The good guys aren’t all good and the bad guys aren’t all bad.

Let’s go.

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