Is Trump Planning to Invade Cuba?

Tommy and Ben dig into a week dominated by ominous signs of regime change, nuclear standoffs, and a “historic” summit that left almost everyone disappointed. First they cover the signs pointing to American intervention in Cuba, including reports of Cuban drones, a possible indictment of 94-year-old Raúl Castro, a visit by CIA director John Ratcliffe, and a full blockade that has left the island in a state of humanitarian catastrophe. Then they look to Bolivia, where supporters of former President Evo Morales have blockaded roads and clashes with police are escalating. When it comes to the war in Iran, the global economy remains paralyzed by the closure of the Strait of Hormuz, while Trump vacillates on whether to restart the war or engage in real talks. The guys also recap Trump's China trip, which turned out to be a dud by almost every measure — no trade deal, no help on Iran, and some deeply alarming comments about Taiwan. And finally, Tommy and Ben are subjected to the sounds of Eurovision. Then Tommy is joined by Pod Save the UK host Nish Kumar to discuss the fate of Prime Minister Keir Starmer and the Labour Party, and the troubling rise of the right-wing Reform UK party. Check out Nish’s special, Don’t Kill My Vibe . For a closed-captioned version of this episode, click here . For a transcript of this episode, please email transcripts@crooked.com and include the name of the podcast, episode title, and episode date. For Friends of the Pod, the boys answer questions about multi-party systems and Obama’s pivot to Asia. Preorder Ben’s book All We Say: The Battle for American Identity: A History in 15 Speeches and

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Is Trump Planning to Invade Cuba? is an episode from Pod Save the World by Audioboom.

This episode is 95:14 long.

This episode was published on May 20, 2026.

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