Trump’s Iran Gamble Is Backfiring

Trump’s Iran Gamble Is Backfiring

June 2, 2026 · 22 min · Season 1 · Episode 22

About this episode

Richard Epstein discusses the implications of modern military strategy and critiques Donald Trump's approach to Iran.

This week, Richard Epstein weighs in on war, deterrence, and the limits of modern military strategy. Drawing lessons from World War II, Vietnam, Gaza, and the current conflict with Iran, Epstein argues that wars are either fought to win or not fought at all. He contends that America’s fear of escalation, reliance on limited objectives, and preference for negotiated settlements have produced strategic drift rather than decisive victory. Professor Epstein also delivers a sharp critique of Donald Trump’s handling of Iran, defends the logic of unconditional surrender, and explains why he believes half-measures can be more dangerous—and more costly—than total commitment.

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