Judging Freedom Judging Freedom

Gilbert Doctorow : Can Ukraine Make it Through the Winter?

Sep 30, 2026 · 22m

Summary

This episode of Judging Freedom features host Gilbert Doctorow analyzing the geopolitical fallout of US-Iran tensions, arguing that Trump's threats likely led to a secret deal rather than war. Doctorow discusses Russian Foreign Minister Lavrov's warnings about a potential NATO-Russia conflict and the strategic importance of Kaliningrad. He also critiques General Keith Kellogg's claims about Russian troop losses and predicts Ukraine's imminent political collapse due to infrastructure destruction and economic bankruptcy. The segment concludes with a dismissal of Mark Rutte's NATO statements, …

Topics discussed

Intro: Preemptive war and the danger of government Sponsor: Expat Money Summit and Plan B strategies Guest intro: Gilbert Doctorow on Trump's Iran threats Historical context: Trump's past threats to North Korea Strait of Hormuz: Evidence of a secret US-Iran deal Assessing the cost and outcome of the Iran conflict US and NATO withdrawal from Iraq Russia's official reaction to Trump's threats Netanyahu's alleged knowledge of October 7 attacks Lavrov on Europe preparing for war with Russia Russia's dual messages: No attack vs. nuclear threat Strategic importance of Kaliningrad and WWII settlement Clip: Keith Kellogg claims Russia is losing troops Doctorow refutes troop loss claims and ceasefire ideas Ukraine's impending collapse and political defeat Russian election reaction to Ukrainian drone attacks Winter energy crisis and the end of the war Clip: Mark Rutte claims Russia is failing Closing remarks and upcoming show segments
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