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School of War

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

School of War · Apr 3, 2026 · 53:35

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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.

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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



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