The Long Game with Jake Sullivan and Jon Finer The Long Game with Jake Sullivan and Jon Finer

Iran’s “Economic D-Day” and the US-Canada Rupture

Aug 27, 2026 · 1h 7m

Summary

Jake Sullivan and Jon Finer analyze the Trump administration’s “economic D-Day” sanctions on Iran, arguing the measures are theatrical and unlikely to force concessions. They discuss the escalating US-Canada trade war, noting Canadian public support for Prime Minister Mark Carney’s hardline stance against US tariffs. The episode concludes with a debate on a new executive order authorizing private companies to conduct offensive cyber operations against foreign criminal groups.

Topics discussed

Intro: Pitch Season 16 and Odo ad Welcome to The Long Game: Economic Warfare Edition Tribute to Dolly Parton: Philanthropy and Legacy Podcast Housekeeping: Subscribe and Review Iran 'Economic D-Day': Context and Strategy Shift Sanctions Details: 60 Entities and China's Role Critique of WWII Analogies and Regime Resilience Negotiation Dynamics: Theater vs. Real Concessions What to Watch: Sanctions, China, and Iran's Internal Debate Odo Ad and Pitch Season 16 Promo US-Canada Trade War: Tariffs and Sovereignty Dispute Canadian Public Reaction and Alberta Independence Referendum Ripple and Shopify Ads New Policy: Private Sector Cyber 'Hack Back' Memo Debate Pro: Need for Offensive Cyber Capabilities Debate Con: Risks of Escalation and Execution Hosts' Verdict on Cyber Privateering Policy Outro: CIA Director in Moscow and Credits Pitch Season 16 Recap and Final Ad
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