Trump Says We’re ‘Winning’ in Iran. It’s More Complicated.

2026-04-03 · 54 min · 10 entities

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mentioned The Free Press company

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mentioned Rafaela Siewert of The Free Press company

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hosted by The Free Press company

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Episode description as stored

The Strait of Hormuz is closed. Iran’s nuclear program survives. And while the regime has been weakened, it remains intact. So what has President Trump accomplished—and what comes next in the war? Today on School of War, we’re doing something a little different. Instead of sitting in the interviewer’s chair, as I usually do – I’m the one being interviewed. I joined Rafaela Siewert of The Free Press to talk through my current thinking on the war in Iran. ▪️ Times 02:03 Trump’s speech 05:22 Escalation 10:10 Goals 12:25 Risk and scale 15:15 Kinds of surprise 17:37 Misreading the Iranians 22:10 15 Points 25:49 Opening the Strait of Hormuz 29:24 Branding 32:44 Oil 37:15 Kharg Island 41:35 Regime alteration 44:20 Time and resources 48:49 Balance 50:11 Trump, MAGA, and the Right Follow along on Instagram, X @schoolofwarpod, and YouTube @SchoolofWarPodcast Find more content on our School of War Substack Learn more about your ad choices. Visit megaphone.fm/adchoices