Iran expert Karim Sadjadpour joins the show to unpack the U.S.–Israel strikes that killed Supreme Leader Ayatollah Ali Khamenei, Iran’s retaliation across the Middle East, and the uncertainty surrounding what comes next in the war. They discuss: 

What happens to the Islamic Republic after the loss of its supreme leader? Is the regime likely to fracture, harden, or consolidate — and how far might retaliation go?

Can the Revolutionary Guards hold the system together? And what are ordinary Iranians thinking as violence escalates?

In a final segment, Jake and Jon turn to Washington, where a standoff between Anthropic and the Pentagon raises significant policy questions about AI, national security, and who sets the rules. 

What does the “supply chain risk” threat mean — and what precedent does this set for frontier AI companies working with the U.S. government?
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