Bob Kagan: We’re About to Find Out What Real Failure Looks Like | Bulwark Podcast

The United States lost the Iran war back in March when Trump chickened out and didn’t retaliate against Tehran once it proved it could inflict economic pain on the Gulf states. While much of the mainstream media keeps hyping the negotiations and the ceasefire, Iran is not making concessions and is focused on shaking Trump down for money. But the biggest loser in this debacle may be Israel, which turned itself from a dominant power in the region to a losing power. And Israel, which the administration is likely to turn against, could be irreparably damaged in U.S. public opinion as well. Plus, the post WWII American-led world order is collapsing, Trump is the worst negotiator, and conquering Cuba will require a major nation-building effort. Bob Kagan joins Tim Miller. Get 20% off your DeleteMe plan when you go to www.joindeleteme.com/BULWARK and use promo code BULWARK at checkout. Show Notes: Bob on Trump's surrender: https://www.theatlantic.com/international/2026/05/trump-surrender-iran-endgame/687252/?gift=AO0MhSsTDaHgiP_RxFGfB_3wkBJWognrgUz4gyZlqqo&utm_source=copy-link&utm_medium=social&utm_campaign=share Bob on the end of the post WWII-order: https://www.theatlantic.com/magazine/2026/03/trump-national-security-greenland-spheres-of-interest/685673/?gift=AO0MhSsTDaHgiP_RxFGfByo5mdzvoO6tGCFwiiPb75Q&utm_source=copy-link&utm_medium=social&utm_campaign=share The Next Level LIVE after the Texas primary: https://youtube.com/live/Vw2RCV0xyiY?feature=share Become a Bulwark Youtube Plus Member here - https://www.youtube.com/channel/UCG4Hp1KbGw4e02N7FpPXDgQ/join Chapters: 00:00:00 Cold open 00:00:21 John Cornyn’s loss 00:03:35 Trump’s “surrender” to Iran 00:05:25 Why the media is getting Iran wrong 00:09:24 Iran’s control of the Strait of Hormuz 00:11:34 Republican pushback and MAGA divisions 00:13:21 Ad break: Delete Me 00:15:41 How Israel is being sidelined 00:18:50 The Gulf states and the Abraham Accords 00:26:46 America’s broader strategic withdrawal 00:29:10 The China summit and Taiwan 00:33:30 Chain reaction in Asia and Europe 00:38:55 Why the hawks got Iran wrong 00:42:35 Foreign policy doctrine and Democratic Party blame 00:54:08 Cuba as Trump’s next potential quagmire