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Is Cuba back on the menu?

May 20, 2026
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Is Cuba back on the menu?
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This story appeared in The Logoff, a daily newsletter that helps you stay informed about the Trump administration without letting political news take over your life. Subscribe here.

Welcome to The Logoff: The Trump administration is indicting former Cuban President Raúl Castro as it seeks to ramp up pressure on the island.

What happened? The indictment against Castro and five others was unsealed in a Miami federal court on Wednesday, but it focuses on conduct from 30 years ago, when the Cuban government killed four people, three of whom were American citizens, by shooting down two small planes. It supersedes an earlier 2003 indictment, which named some of the same defendants.

What’s the context? President Donald Trump’s pressure campaign against Cuba escalated at the beginning of this year with his removal of Venezuelan President Nicolás Maduro in January and the announcement of a hemispheric “Donroe Doctrine.”

Since then, Cuba has been under a US oil blockade (with some exceptions), resulting in widespread blackouts and a humanitarian crisis impacting the island’s 10 million residents.

Cuba is also a particular cause of Secretary of State Marco Rubio, who has long wanted to topple the country’s communist regime.

What’s the big picture? Trump already has one war on his hands in Iran, so it’s hard to gauge his appetite for more military adventurism at just this moment. But Wednesday’s indictment is yet another escalation, and it’s reminiscent of the superseding indictment that the Trump administration filed against Maduro after his capture earlier this year. Maduro was also indicted in a US court in 2020, and the Trump administration has framed his removal as a law enforcement operation.

Politico’s Nahal Toosi also reported this week that Trump and his advisers “have grown frustrated” with the lack of any significant concessions from Cuban leaders to date and are beginning to more seriously consider military options.

Acting Attorney General Todd Blanche said Wednesday that the Castro filing “isn’t a show indictment.”

“There is a warrant issued for his arrest,” Blanche added. “We expect that he will show up here by his own will or by another way.”

And with that, it’s time to log off…

There’s a long list of US-specific ways in which the upcoming World Cup, hosted jointly by the US, Mexico, and Canada, is shaping up to be a mess. (NJ Transit, I’m looking at you.) But here’s one really cool benefit: It’s fueling a soccer boom in New York City, and new soccer pitches are getting built to meet that demand. You can read all about it here with a gift link.

Have a great evening, and we’ll see you back here tomorrow!



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