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Jared & Ivanka Conquer Albanian Island

Explore episode Jun 10, 2026
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What Would a Cuba Operation Actually Look Like?

Jared & Ivanka Conquer Albanian Island · Jun 10, 2026 News

A military operation against Raul Castro at 95 would inflame Cuban nationalism. Targeted action against younger leadership is possible. Boots on the Malecón seems outlandish but felt equally outlandish before Venezuela. Grant says the safest path for Cuba is a negotiated solution that means wholesale economic and political transformation — but no one knows if Havana is capable of going there.

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Will Grant: CIA Director Ratcliffe in Havana and What Comes After Venezuela

At 1:11:35 · chapter starts 1:08:20

Tommy raises the extraordinary fact of CIA Director John Ratcliffe's visit to Havana, which came directly after the Venezuela operation. Grant says he was standing on the Malecón during a Cuban government-organized protest outside the US Embassy when he learned Ratcliffe had gone to Venezuela — and then showed the news to a Cuban official, watching him 'literally turn gray.' Grant walks through the message Ratcliffe likely delivered: we indicted Raul Castro, we just demonstrated in Venezuela that we are capable of military action, and more than 34 of your soldiers were killed by Delta Force in seconds. He then analyzes the Cuba operation options: a personal action against the 95-year-old Castro would inflame Cuban nationalism even among those who want change; targeted action against younger leadership is more plausible; boots on the Malecón seemed outlandish even seven months ago, as Venezuela did. The only truly safe path for Cuba, Grant says, is a negotiated solution — but it requires wholesale economic and political transformation that Rubio will demand and that Havana may not be capable of delivering.

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