Jay is joined by geopolitical analyst and forecaster George Friedman to unpack what President Trump really represents in the long arc of American history. We revisit George’s “vanilla president” thesis and why, personality aside, Trump’s project to dismantle the post-1945 world order was predictable and perhaps inevitable. We dig into the shift from global policeman back toward U.S. isolationism, the real story behind Venezuela and the U.S. military build-up in the Caribbean, and why a renewed Russia–Cuba pact makes the Florida Straits one of the most important choke points on Earth.