Astead Herndon is frustrated by polling. After a career spent speaking directly with voters around the country about their priorities, he has found that the flat numbers of surveys rarely capture the complex realities of Americans. I sat down with Herndon, recently named editorial director of Vox after covering elections for The New York Times since 2018, to reflect on the past decade of voters’ choices and what they reveal about the nation’s identity. While Herndon and I agree about the seismic impact of President Donald Trump’s 2016 victory on the news media, we disagree on the role racism played in his election. We had a productive debate as we discussed why black male voters shifted toward Trump in 2024. We also delved into New York City politics, examining how Mayor-elect Zohran Mamdani’s positions evolved over the course of his campaign and the challenges he will face in office as he tries to get things done while maintaining the expectations of his base. This conversation is full of insights on how the media can better understand the country, and proves that healthy disagreement can be as enlightening as agreement. 00:00 – Intro 1:00 - Ad 01:31 - 2016: How Trump’s Win Changed Their Worldviews 10:05 - Race, Identity & the Obama-to-Trump Voter Puzzle 16:23 - Why Voters Defied Elite Narratives 19:14 - What Mamdani’s Win Actually Signals 23:42 - Mamdani 1.0 → 2.0: The Policing Pivot 29:25 - Crime, Affordability & What Voters Truly Care About 33:34 - Ad 33:50 - The Limits of Polling & Why It Misses Real Sentiment 39:25 - Why Has Trump Gained Support with Black Men? 43:19 - Mamdani, Israel, & Ideological Red Lines 49:29 - Rent Freeze, Economics & Policy Reality Checks 55:30 - What a Mayor Can Actually Do (and What Mamdani Can't) 58:39 - 2028 & Beyond: Who Do Democrats Run? 1:01:17 - Closing and Where to Find Astead