Matt Wing, a political strategist and founder of Wingspan, joined the show to analyze the first of two televised debates in the general election for Mayor of New York City and what comes next. Zohran Mamdani, Andrew Cuomo, and Curtis Sliwa debated on NBC NY on the night of Thursday, October 16, 2025, and this conversation between Wing and host Ben Max was recorded right after. (Ep 535)