Impolitic with John Heilemann Impolitic with John Heilemann

Dave Regan: Will California Kick Its Billionaires in the Bollocks?

Sep 4, 2026 · 1h 25m

Summary

John Heilemann interviews SEIU leader Dave Regan, the architect of California’s Proposition 40, a one-time 5% wealth tax on billionaires designed to offset federal healthcare cuts. Regan defends the measure against opposition from Governor Gavin Newsom and Silicon Valley elites, arguing it addresses extreme inequality and prevents a public health crisis. The discussion covers the political strategy behind using ballot initiatives and the broader ideological battle over taxing the ultra-wealthy.

Topics discussed

Intro: Sleep hygiene, ChiliPad, and Quince hoodie ads Context: California ballot measures and Prop 40 wealth tax Interview Intro: Dave Regan and SEIU background The Rationale: Federal cuts and the need for a wealth tax Wealth Inequality: Billionaire wealth vs. median income Mechanics: How the 5% one-time tax is calculated and paid Criticism: Why a temporary 5-year solution is necessary Ad Break: IXL learning platform Exodus Argument: Will billionaires leave California? Dave Regan's History: Union leadership and past initiatives Negotiations: Failed talks with Gov. Newsom Political Dynamics: Newsom's opposition and billionaire influence Ad Break: Indeed Sponsored Jobs Polling and Opposition: Split in Democratic support Becerra and Newsom: Presidential ambitions vs. Prop 40 National Impact: Prop 40 as a blueprint for other states Conclusion: Democracy, accountability, and final thoughts
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