Saikat Chakrabarti has audacious plans to change American politics.
By Alex Thomas
October 30, 2025
SAN FRANCISCO — Saikat Chakrabarti faces a daunting enough task in trying to oust Nancy Pelosi from Congress. And now here he is, daydreaming about targeting her successor in Democratic leadership.
“Imagine if we go after Hakeem Jeffries as our first thing,” he says. “That will raise a ton of money right now, in this moment.”8
This moment, in Chakrabarti’s mind, is the prospect of a populist uprising on the left that spans the country, and one that he is hoping to ride to victory in his primary challenge against the former speaker. And then, after taking down a political giant, comes the hard part: transforming the Democratic Party. So I’m in the open-floor office of his upstart campaign in San Francisco, asking about money for how he’ll fuel his revolt against the establishment. I’m asking about money because I’m trying to grapple with Chakrabarti’s vision for reshaping the political landscape, which feels far-fetched, but which he has already done once before. Kind of.
Saikat (pronounced Shoy-kaht) Chakrabarti isn’t your typical primary challenger, and this isn’t his first time trying to play on a major political stage.
Chakrabarti’s re-emergence comes eight years after he co-founded Justice Democrats, that badgery rank of progressive outsiders who crashed Capitol Hill in President Donald Trump’s first term, fueling a constant diet of stories with some version of Dems in Disarray. After managing the campaign for Alexandria Ocasio-Cortez’s stunning upset victory in 2018, Chakrabarti spent eight months on the Hill as her first chief of staff where he admits to “ruffling feathers.” Some have sharper words — Drew Hammill, the former longtime Pelosi spokesperson, told me that I would be “hard-pressed to find any member that served at the time that doesn’t remember this guy threatening to take down Democratic members of our own caucus.”
The Justice Democrats have taken some hits in recent years — Cori Bush (D-Mo.) and Jamaal Bowman (D-N.Y.) lost primary challenges in 2024 — but the group’s arrival underscored the power of the Democratic Party’s left flank, and now Chakrabarti envisions something still bigger.