Hacks On Tap No Sleep Till City Hall (with Howard Wolfson)
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Oct 21, 2025 Howard Wolfson, an experienced political strategist and former New York deputy mayor now at Bloomberg, delves into the dynamics of the New York mayoral race. He discusses Mamdani's ascent and Cuomo's vulnerabilities, while evaluating Curtis Sliwa's impact on the contest. The conversation shifts to national trends, with a focus on how affordability shapes Democratic strategy in New Jersey and Virginia. Wolfson also addresses California's Prop 50, the ongoing protests for democracy, and the implications of Trump's AI-driven antics on political norms.
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Affordability Fueled A Political Upset
- Zoran Mamdani surged by focusing relentlessly on affordability, energizing young and immigrant voters.
- His win exposed establishment failures and reshaped New York's primary dynamics overnight.
Entertainer Candidate Keeps Race Three-Way
- Curtis Sliwa thrives as a performer and has no intention of exiting the race despite establishment pressure.
- His continued presence makes the three-way dynamic permanent and complicates outcomes.
First Appointments Will Reveal His Mode
- Mamdani moved off defund-the-police rhetoric but establishing cooperation will be a choice for New York's establishment.
- Early appointments (e.g., police commissioner) will reveal whether he'll govern pragmatically or ideologically.