In a surprising political showdown, Saikat Chakrabarti, a 39-year-old Democratic Socialist with deep roots in progressive politics, is challenging Speaker Emerita Nancy Pelosi for her San Francisco congressional seat in the 2026 election.

Chakrabarti, known for his work with Bernie Sanders and Alexandria Ocasio-Cortez’s campaigns, launched his campaign at The Chapel in the Mission district, drawing a packed crowd of around 600 supporters. With a bold and urgent tone, he declared, “It is clear as daylight: We are living in the middle of a fascist coup. This is about an overwhelming demand for change right now”.

Despite his progressive credentials, Chakrabarti brings a complex political profile. As a founding engineer at Stripe, he’s amassed a net worth of approximately $170 million - higher than Pelosi’s own wealth. Acknowledging this potential contradiction, he told the audience, “I did not work harder than my teacher or a nurse or the people cleaning our offices. I just won the startup lottery”.

His campaign faces significant challenges. Pelosi has consistently won her district for 20 consecutive elections, and Chakrabarti’s internal polling suggests only that 51% of voters think it’s time for change - not necessarily that they’d support him specifically.

Additionally, Chakrabarti’s political history includes controversial donations that might alienate fellow Democratic Socialists. He previously contributed funds to defeat DSA member Dean Preston, which could complicate his grassroots support.

The primary election is scheduled for June 2, 2026, with the general election on November 3. Interestingly, both Pelosi and Chakrabarti could potentially advance to the general election if they finish in the top two during the primary.

As San Francisco prepares for this high-stakes political battle, Chakrabarti represents a new generation of politicians challenging established Democratic leadership, promising “transformational change” in an era of increasing political polarization.