The Five The Five

Midterms Mistake

Sep 21, 2026 · 46m

Summary

Hosts Jesse Waters, Kaylee McInerny, Harold Ford Jr., Martha McCallum, and Kennedy debate whether the Democratic Party’s association with the DSA and streamer Hasan Piker is a fatal brand error for the midterms. The panel also discusses the conflicting approaches to AI regulation, contrasting President Trump’s new "AI Force" with Governor Newsom and Barack Obama’s push for government oversight. Additionally, they analyze the political implications of President Trump meeting with NYC Mayor Zohran Mamdani and Ed Sheeran’s apology after dropping Macklemore from his tour.

Topics discussed

Sponsor: Caesar Dog Food Intro: Democrats and DSA relations Debate: Democrats distancing from socialism Midterm outlook and Tea Party comparison Rise of Democratic Socialists in primaries Hassan Piker's influence and AOC's stance Critique of anti-Semitic socialism and Piker Economic factors and Iran strategy Transition: Trump and Obama on AI regulation Newsom, Hochul, and Obama push AI regulation Critique of AI regulation and past failures China, AI guardrails, and geopolitical risks Big Tech CEOs and AI safety concerns Bipartisan agreement on AI oversight Transition: Trump meets Mayor Mamdani Trump and Mamdani meeting at Gracie Mansion Political dynamics: Trump and NYC Mayor Historical context: Reagan and Tip O'Neill Trump's strategy of engaging with opponents Sponsor: Lincoln Rejuvenate Ed Sheeran and Macklemore controversy Artist freedom vs. venue content policies Capitalism and private stadium funding Sponsor: SimpliSafe Viral trend: Iced coffee in job interviews Sponsor: Caesar Dog Food Today in History: Sandra Day O'Connor Outro and subscription info
Listen ad-free on Castria