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

Treasury Secretary Scott Bessent says the U.S. is entering “the endgame” with Iran, launching what he calls an “economic D-Day.” Closer to home, U.S.-Canada trade talks have collapsed after Prime Minister Mark Carney rejected Washington’s latest demands. 

Jake Sullivan and Jon Finer examine whether Operation Economic Outcast can change Iran’s calculus, why China holds the key, and why Canadians are backing a trade fight they expect to hurt. They also stage a Red Team/Blue Team debate over President Trump’s new cyber memo, which allows private companies to conduct offensive operations against foreign cybercriminals. Jon makes the case for the so-called cyber privateers, while Jake lays out the risks.

Subscribe to The Long Game+ on Apple podcasts or on Substack for access to exclusive segments. This week, Jake and Jon tackle two listener questions: What should we make of CIA Director John Ratcliffe’s unannounced trip to Moscow? And, how did Jake and Jon manage the physical and mental toll of their years as national security advisors? 

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