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What Democrats Get Wrong About Winning Elections

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November 15, 2025

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Good policy is good politics, or so the saying goes. So, uh, how do we agree on what that is?

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Jane Coaston talks with three of the left’s most prominent policy thinkers: Democratic strategist Waleed Shahid, Neera Tanden of the Center for American Progress, and writer Matthew Yglesias of Slow Boring.

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If you’re looking for hype, fake outrage, and groupthink, kindly keep moving. Our mission at What a Day is simple: to be your guide to what truly matters each morning (and the fun stuff you might have missed) in just 20 minutes. Host Jane Coaston brings you in-depth reporting and substantive analysis on the big stories shaping today and the creeping trends shaping tomorrow—and when she doesn’t know the answers, she asks someone even smarter to fill us all in. Radical, right?

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Crooked believes that we need a better conversation about politics, culture, and the world around us—one that doesn’t just focus on what’s broken, but what we can do to fix it. At a time when it’s increasingly easy to feel cynical or hopeless, former Obama staffers Jon Favreau, Jon Lovett, and Tommy Vietor have created a place where people can have sane conversations that inform, entertain, and inspire action. In 2017 they started Crooked with Pod Save America—a no-bullshit conversation about politics. Since then, we continue to add shows, voices, and opportunities for activism, because it’s up to all of us to do our part to build a better world. That’s it. End of mission.

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Guests & Subjects Covered

Jane CoastonWaleed Shahid Neera TandenAmerican ProgressMatthew YglesiasPolicy PrioritiesAd BreakBig TentBold Policies

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What Democrats Get Wrong About Winning Elections · Pod Save America · Sentinel