COL. DOUGLAS MACGREGOR : The Middle East Isn’t De Escalating And Neither Is Ukraine episode artwork

EPISODE · Jun 3, 2026 · 53 MIN

COL. DOUGLAS MACGREGOR : The Middle East Isn’t De Escalating And Neither Is Ukraine

from JIM WEBB PODCAST · host Produced and Distributed by OMG Media Partners, LLC.

The world can look calm for a day while the map is quietly catching fire. We start with rapid updates from the Persian Gulf and immediately ask the uncomfortable question: if strikes are landing in Kuwait and pressure is building on the U.S. Fifth Fleet, what does “de-escalation” even mean anymore? With Doug McGregor, we break down why the Strait of Hormuz is the real strategic choke point, why Iran’s anti-access tools change the risk calculus, and why financial markets can talk themselves into a story that the battlefield does not support.Then we connect the Gulf to the wider Middle East war arc, including Israel’s expanding operations in Lebanon, strikes in Beirut, and evacuation orders that reshape the regional incentive structure. Doug argues that Iran is gaining stature across the Muslim world by positioning itself as the power willing to resist while Gaza and southern Lebanon absorb the blows, and he explains how that can fuel new alignments, weaken old diplomatic projects, and increase the odds the U.S. gets pulled deeper in despite a lack of a clean exit plan.From there, we pivot to the Russia Ukraine war and the question many Americans are no longer hearing asked: what does the endgame look like if Russia chooses decisive operations toward Kiev or Odessa? We talk logistics, timing, corruption, casualty realities, and the dangerous appeal of an insurgency strategy, plus why borders and local identity in Ukraine never fit the simplistic narratives. We close with a hard conversation about alliance commitments, “limited liability” foreign policy, and the push for a viable third party through the National Conversation.Subscribe, share this with a friend who follows geopolitics, and leave a review so more people can find the showChapter Markers0:00. Breaking News And War Updates1:24. Sponsor Shoutout And Doug Returns2:30. Coffee Branding And Bombs Away Beer4:48. Is The Iran Ceasefire Real8:53. Lebanon Escalation And Iran’s Calculus14:18. Turkey, NATO, And Europe’s Future16:25. Markets, Inflation, And Oil Reality21:40. Ukraine Ground Truth And Russian Options29:29. Attrition, Corruption, And Insurgency Risk41:45. Borders, Plebiscites, And Staying Out44:14. Limited Liability Foreign Policy And Third Party51:44Final Thoughts And Listener SupportSupport this podcast at — https://redcircle.com/jim-webb-podcast/donationsAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy

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COL. DOUGLAS MACGREGOR : The Middle East Isn’t De Escalating And Neither Is Ukraine

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This episode was published on June 3, 2026.

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The world can look calm for a day while the map is quietly catching fire. We start with rapid updates from the Persian Gulf and immediately ask the uncomfortable question: if strikes are landing in Kuwait and pressure is building on the U.S. Fifth...

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