SHOW / EPISODE

COL. DOUGLAS MACGREGOR: Trump administration falling into the abyss and it may already be too late

52m | Sep 8, 2026

The Persian Gulf isn’t a chessboard, it’s a map with consequences, and we keep acting like geography doesn’t matter. Col. Douglas MacGregor joins us to connect a brutal Civil War lesson from Fredericksburg to today’s Strait of Hormuz reality: Iran sits close, mobilized, and treats this as existential, while the United States signals strength with forces that can be pushed offshore by drones and missiles.


We get into what a “blockade” really means when logistics are stretched, oil prices jump, and the Strategic Petroleum Reserve is no longer the backstop people assume. From there, we zoom out to the political layer: why Congress so often follows the same donors across party lines, why a mass casualty event might trigger “why are we there?” instead of a rush to war, and how the growing people versus state divide in Europe could foreshadow turbulence in the United States.


Then we tackle leadership and modernization: perverse incentives in the senior ranks, too many cooks at the top, and why the US military talks about experimentation but too often rigs the outcome. Doug also argues that Iran and Russia are civilizational states that fight differently when they believe survival is on the line, and that misunderstanding that mindset leads to disasters we could have predicted.


If you found this useful, subscribe, share the episode with a friend, and leave a review so more people can find it. What do you think is the hardest truth Washington is refusing to face right now?

Chapter Markers

  • 0:00 Labor Day Return And Guest Setup
  • 2:50 Fredericksburg Lessons For Modern War
  • 5:00 Iran’s Geographic Advantage In The Gulf
  • 14:20 Mass Casualties And Congress Incentives
  • 18:30 The Growing Divide Between People And State
  • 23:20 Empire Thinking And The Petrodollar Bargain
  • 27:30 Drones Missiles And A Navy Pushed Offshore
  • 30:40 Why Military Experimentation Keeps Failing
  • 32:00 Senior Leader Turnover And Broken Incentives
  • 40:40 Total War Mindsets In Iran And Russia
  • 46:10 Civilizational Blind Spots And Unsustainable War
  • 50:30 Reexamining Strategy And Final Takeaways




Advertising Inquiries: https://redcircle.com/brands

Privacy & Opt-Out: https://redcircle.com/privacy
Paused
Audio Player Image
JIM WEBB PODCAST
Loading...