Saikat Chakrabarti likes to call himself a proud “class traitor” on the campaign trail, and San Francisco is where he claims he first turned.
It was in 2013, and Chakrabarti was starting to feel the seams of his career coming loose.
Two years prior, he had joined a fintech startup in the city called Stripe as a founding engineer. He had ambitions of building tools to support microfinance, labor, and nonprofits. Instead, the company felt like it was sliding into “an increasingly corporate phase,” Chakrabarti told me recently over a glass of green tea at Tarragon Cafe in the Lower Haight, just minutes from his home in Duboce Triangle.
It wasn’t what he signed up for. “It’s hard to imagine today, but there used to be an ethos in the industry with the decentralized open-source movement, a big anti-surveillance push, that kind of culture I was a part of,” Chakrabarti said. “Like, ‘Let’s use tech to liberate people.’ Versus the massive conglomerates that rule now.”
Ironically, his early equity in Stripe made Chakrabarti hugely rich; the company now sits at a valuation of $159 billion. His net worth — unclear but enough to make him a centimillionaire — feels like an inconvenient truth amid his hard-charging campaign to become San Francisco’s next congressional representative.
Congress is uncharted waters for Chakrabarti, who has some experience in federal politics but little as a legislator. During our hour-long talk, he showed how clearly he wants to play the outside revolutionary. I could also see how much thought he’s put into crafting that image: Chakrabarti comes off as very articulate but also over-prepared, so much so that it’s hard to glean his inner world.
Born in Fort Worth, Texas, to Bengali immigrants from India, Chakrabarti landed at Harvard University and graduated with a degree in computer science in 2007.
A week-long visit to the Bay Area during college had Chakrabarti daydreaming about moving here, and after a stint with a hedge fund in New York City, he arrived in San Francisco in 2009 and co-founded a website design company. Chakrabarti spent three months in an apartment in Park Merced, then moved to a unit at 16th and Hoff streets in the Mission.
To a kid from a Fort Worth suburb, the Mission felt like an explosion of noise, color, and creativity. Chakrabarti, who “didn’t have much money back then,” fondly reminisces about the dollar tacos at Pancho Villa and slices from Arinell Pizza (RIP) that kept him afloat. The idealism of the city struck a chord.
“San Francisco is associated with all these social justice movements that were famous, like the gay rights, disability rights, anti-war movements,” Chakrabarti said. “Growing up in Texas, I just craved that so hard.”
It’s confusing to square that observation with Chakrabarti’s own admission that he “wasn’t political at all” during his early years in the Bay, even as he joined groups like Noisebridge, the hackerspace at 272 Capp St. with a distinctly anarchist viewpoint.
As with a lot of millennials, however, Chakrabarti’s interest in politics exploded when he learned about Bernie Sanders. Hearing a Democrat criticize his own party for its corporate cronyism and warmongering in the Middle East was a lightbulb moment, Chakrabarti said. Using his comp-sci skills, Chakrabarti became director of organizing technology for Sanders’ campaign. He also helped oversee “barnstorms” designed to turn out large crowds and bring in volunteers, most of whom had no prior experience.
When the Sanders campaign fell short in the primary and the establishment-preferred Hillary Clinton became the nominee, Chakrabarti took his newfound skills and built a political action committee, Brand New Congress, and then another PAC and caucus, dubbed Justice Democrats. Both shared a game plan: leveraging grassroots mobilizing to pressure Congress from the outside and actively recruiting new blood to run for office.
I could see this blueprint at work at Chakrabarti’s May 7 rally, when he packed a SoMa nightclub with more than 1,000 people who came to see him, leftist streamer Hasan Piker, and a slate of young Justice Democrat candidates pledging to “Change the Party” (a slogan that sent at least one San Francisco elected official spiraling). Former New York City Rep. Jamaal Bowman, who won his House seat in major part due to Justice Democrats’ backing, got the crowd roaring with his cries for revolution (including a Wu-Tang shoutout). Piker got the loudest cheers; it felt like every young man in the crowd was there to see him.
One rally buoyed by a socialist celebrity does not a campaign make, but it was a rebuke against persistently negative discourse about one aspect of Chakrabarti’s past: His uncertain relationship with Rep. Alexandria Ocasio-Cortez.
Local and national media alike have fixated on Ocasio-Cortez’s unwillingness to comment on Chakrabarti’s campaign, especially since she was hand-picked by Brand New Congress and the Justice Democrats and beat an incumbent Democrat in 2018. Chakrabarti was her chief of staff for about eight months, working on the Green New Deal and serving as AOC’s spokesperson, until he resigned in August 2019. Observers blamed the split on his fiery social media criticisms of fellow Democrats, and AOC’s consequent disapproval.
I didn’t even bother pressing him about this, because Chakrabarti has acted, in multiple interviews, as if her silence is no big deal and that he hopes for her endorsement. If it’s true that the split is because he tweeted too close to the sun (“segregationists” struck a nerve), I’m not sure how it hurts his brand; he’s been the noisy leftist in the proverbial room for a long time. When I asked him about the tension between AOC and Pelosi on the subject of the Green New Deal, Chakrabarti talked like it was all a part of the plan.
“We knew the media wanted to report on the so-called fight between them, even though there wasn’t really one. We were like, ‘Sure, we’ll give it to you.’ Then the right-wingers attacked it a bunch. It was great because it kept the [Green New Deal] in the media, and we kept momentum building,” Chakrabarti said. “I used all that attention to build coalitions, talking with unions, with members of Congress.”
With or without AOC’s endorsement, what is more concerning is whether Chakrabarti really understands the “knife fight in a phone booth” of San Francisco politics. He’s broken the city record on spending for a congressional race, but the majority of his individual donations have come from outside the city, partly due to the Justice Democrats network attracting leftists from around the country.
Despite calling San Francisco home, he barely participated in a decade of city elections, and spent time living in places like New York, New Jersey, and Nevada while working in federal politics. (One local provocateur keeps showing up to Chakrabarti’s events in a minivan wrapped in signs that claim Chakrabarti “lives in Maryland.” The candidate blames an error in listing a Maryland home as his primary address, which he has since changed.)
And when he did get involved in local politics, Chakrabarti backed centrist candidates like Daniel Lurie and Bilal Mahmood, the latter who unseated incumbent socialist Supervisor Dean Preston in 2024. (Chakrabarti recently claimed Mahmood is “a progressive.”)
For how muddy his San Francisco politics can be, Chakrabarti comes alive when talking about his policy ideas.
He spoke a mile a minute about gentrification, tying it to a lack of comprehensive social housing programs that sustain mixed-income communities, and how nations like Austria and Singapore have gotten political buy-in from residents of all tax brackets. He also beamed when I asked about his concept of publicly owned AI, in which the government would offer the tech as a kind of utility.
“We’ve got to get out of this stranglehold that private corporations have on our economy, where they’re constantly telling us that if you piss them off, our economy is going to collapse because we rely on them,” Chakrabarti said.
Chakrabarti’s work with New Consensus, an economic think tank he co-founded, is dedicated to making long-term plans for national economic development. Wrangling AI is a core piece of that strategy. Having organizations use publicly owned AI could keep them protected from corporate machinations and give workers more control over impacts to their livelihoods, he said.
“What I don’t want to happen is that industries like insurance underwriting or financial services get sucked up into these massive AI monopolies that will just collect rent off what is essentially a free service,” Chakrabarti said. “If something is free, the government should just provide it for free. It’s a way to, you know, own the means of production, right?”
Strategically dropping Marx is like the cherry on a sundae for any card-carrying leftist, and also something that I don’t think Pelosi’s ever done. For all the questions of how committed Chakrabarti has been to San Francisco politics, his eagerness suggests that he’s in it for the long run.
At one point during his rapid-fire take on the enshittification of the University of California healthcare system, Chakrabarti stopped himself. “I’m sorry for rambling,” he told me.
I didn’t mind: He’s good at talking. If you’re going to be a real class traitor in San Francisco, however, you have to prove it. In a week, we’ll find out whether Chakrabarti will get the chance.
