Saikat Chakrabarti: Is San Francisco Ready for Change After 40 Years of Pelosi?

In this episode, I sit down with Saikat Chakrabarti, the architect behind Alexandria Ocasio-Cortez’s 2018 upset and now a 2026 congressional candidate challenging Nancy Pelosi, for a conversation about the future of the Democratic Party, economic transformation, and the urgent fight to restore trust in American democracy.

Saikat opens up about his decision to run against Pelosi, describing it as a generational call for change in a party that has grown too comfortable managing decline rather than delivering progress. He outlines his campaign platform centered on universal healthcare, ending political corruption, and rebalancing the economy through a wealth tax and investment in public infrastructure. Drawing inspiration from FDR’s New Deal, Saikat’s “Mission for America” proposes a national plan to rebuild housing, transit, and energy systems through coordinated public and private partnerships.

We also dive into the structural barriers facing progressives, from corporate influence and establishment resistance to ineffective party leadership under figures like Hakeem Jeffries. Saikat and I discuss how Democrats have lost working-class trust and what it will take to regain it through clarity, courage, and grassroots organization. The conversation underscores a growing frustration with incrementalism and a demand for bold, measurable change that voters can feel in their daily lives.

We close with a reflection on the importance of building lasting movements, the lessons he learned from working with Bernie Sanders and AOC, and the hope that a new generation of progressives will step up to build a government capable of delivering for everyone, not just the wealthy few.

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