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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