How Democratic Socialists Captured City Hall

When the Mayor of a major American city responds to the flight of its largest taxpayers with a laughing “Bye,” it isn’t just a viral clip. It’s a mission statement. For decades, blue city politics was defined by moderate Democrats and corporate compromise. But in 2026, the "machine" has been rebuilt. In this episode, Grant is joined by Austin Berg, Executive Director of Chicago Policy for the Illinois Policy Institute, to look past the rhetoric and into the new mechanics of municipal power. They discuss the "dossier" of Democratic Socialists of America (DSA) members who have moved from outside the gates to the levers of executive power. From the "tax the rich" performance of NYC’s Zohran Mamdani to the institutional capture of Chicago’s administrative agencies, they explore what happens when "the dog catches the car" and activists actually have to deliver results. Connect with Austin Berg: Substack: https://www.thelastward.org/ X: https://x.com/Austin__Berg Writing & Research: https://www.illinoispolicy.org/author/aberg/ 00:00 Cold Open: The Dog Catches the Car 00:58 Introduction: Austin Berg and the DSA Influence 02:30 Video Analysis: Mamdani’s "Terror Tax" and Griffin’s Response 05:45 Results vs. Intentions: The Seattle Starbucks Boycott 09:45 The Wealth Tax Illusion: Why US Cities aren't European Democracies 11:40 The Resilience of New York vs. the Exit of Ken Griffin 14:40 Learning Hard Lessons: Lessons from the California Wealth Tax 15:50 Patient Zero: How Bernie Sanders 2016 Transformed the DSA 18:30 The Municipal Strategy: Why Local Elections are Easy to Sway 20:45 Tactics of the Vanguard: Obstruct, Appoint, and Primary 22:45 Follow the Money: The Role of Government Sector Unions 26:15 Chicago’s Squad: Performative Policy vs. Ward Service 29:40 The Public Safety Debate: ShotSpotter and Ideological Litmus Tests 32:50 Economic Stagnation: Head Taxes and Millionaire Surcharges 35:50 Personnel is Policy: The Infiltration of Appointed Leadership 40:45 Cops are Pigs: Activist Rhetoric vs. Professional Governance 44:30 Is the Vibe Shifting? Lessons from San Francisco’s Rebound 48:30 The Solution: Why Chicago Needs a City Charter 50:20 Being "Long" on Chicago: Man-made Problems and Man-made Solutions Learn more about your ad choices. Visit podcastchoices.com/adchoices