“I really thought after Trump’s second election, the Democrats would have some sort of ‘come to Jesus’ moment,” says former political adviser Saikat Chakrabarti. “I saw none of that. I even saw Nancy Pelosi asked point blank, ‘what did the Democrats do wrong?’ And her answer was basically nothing... I just feel like it’s completely inadequate.”
That’s why Chakrabarti, 39, has decided to run for Congress himself. He has worked on progressive campaigns for Bernie Sanders and Alexandria Ocasio-Cortez (AOC). Now, he wants to help catalyse a generational and ideological shake-up in Washington and emulate the success of New York Democratic mayoral candidate Zohran Mamdani. His goal is to “completely change the brand of the Democratic party”, which faces its lowest favourability ratings on record according to some recent polls.
But first, he needs to win the Democratic nomination—and it just so happens that the district he is running to represent is the Californian seat currently occupied by Pelosi. The 85-year-old Democratic powerbroker has filed the paperwork to run for a 21st term, but hasn’t yet confirmed whether she intends to stand. If she does, she could face her fiercest battle in decades. Polling by GrowSF suggests Chakrabarti has “a better shot than any challenger in many years”.
His campaign has parallels to AOC’s primary run against 10-term incumbent Joe Crowley in New York in 2018. Chakrabarti was instrumental in the campaign’s success: with his campaign group Justice Democrats he recruited AOC to run, before serving as her campaign chair and, later, her chief of staff.
Chakrabarti and AOC would go on to collaborate on the Green New Deal (GND), which framed selling large-scale climate investments as economic opportunities for the working class. To force the GND onto the legislative agenda, they even conducted a sit-in alongside climate activists in the office of Nancy Pelosi, who was then House Speaker.
Chakrabarti’s confrontational approach often jarred with the conciliatory urgings of other Democrats. After fighting with moderate Democrats on Twitter, he ended up leaving the role, moving to the thinktank New Consensus to further champion the GND.
“When we launched the GND, [Pelosi’s] reaction to it was to try to stop it, instead of using that energy to turn it into something. I think that’s the wrong way to do politics today,” he says.
One thing that won’t change if Chakrabarti is elected is that California’s 11th district will still be represented by one of the wealthiest members of Congress—his net worth is at least $167m. Prior to entering politics, he worked in Silicon Valley as a founding engineer at financial services company Stripe. Its early investors included Elon Musk and Peter Thiel, who he describes as “opportunists”.
He met Thiel once, when he gave a presentation at Stripe. “He told us how diversity is the source of weakness in our start-up”, says Chakrabarti disdainfully. Chakrabarti’s father migrated to America from India.
“A lot of what I saw in tech was sort of what drove me into progressive politics,” he says. “I worked hard and I’m proud of some of the work I did, but I didn’t work harder than a teacher or a nurse or a sanitation worker. It’s completely crazy that I worked hard for two years and now, if I wanted to, I could never work another day in my life. Other people who are working hard every day will never be able to afford a home.”
Chakrabarti is a slick and charismatic speaker, and he’s palpably frustrated at how stagnant Washington can be. He recalls his very first chiefs-of-staff meeting: “I thought, this will be where we strategise how to fight back against Trump, right? Wrong.” Instead, colleagues discussed complaints that there were “too many staffers in the members’ elevators”. “These petty rules make no sense in the context of an authoritarian takeover!”
I joke that, with his tech background, Chakrabarti wants to “move fast and break things”. He laughs, but doesn’t protest.
