On a drizzly Monday night in November, as many as 150 attendees crowded into a community center in the Richmond District for an evening with one of the more intriguing political figures in California: Saikat Chakrabarti, a contender for the Congressional seat long held by Nancy Pelosi. 

His appeal is obvious. As San Francisco lurches to the right, many long-time residents feel powerless as they watch the uber-wealthy take control of their city. Chakrabarti, former chief of staff for Democratic Party star, U.S. Congresswoman Alexandria Ocasio-Cortez, served up a host of progressive policy prescriptions, drawing obvious comparisons to recently elected New York Mayor Zohran Mamdani.

Until recently, his only opponent was state Senator Scott Wiener. The contrast between the two Harvard graduates could not be more pronounced. Wiener is a policy wonk short on charm while Chakrabarti is shy of specifics, but blessed with an abundance of charisma. One looks bad in a suit, the other looks good in a T-shirt. While Chakrabarti promises to take no corporate money, Wiener is known for his coziness with real estate developers, who have lavishly funded his campaigns. So it’s hard to blame Chakrabarti’s audience for its willingness to believe what would have sounded to more jaded ears as platitudes. 

Despite a presentation tailor-made to appeal to local progressives, Chakrabarti’s actions in recent city elections raise troubling questions. As former supervisor and recent mayoral candidate Aaron Peskin (who employed this author as director of engagement during his 2024 campaign) bluntly put it: “He has absolutely no track record of doing anything or being part of any political movement beyond a few moderate political donations. He can run around and claim to have some storied history with AOC, but I don’t think he is qualified to represent San Francisco.”

Another concern: Chakrabarti’s resume does not suggest much of a commitment to progressive causes, particularly here in the city. Founder of online payment service Stripe, Chakrabarti is a bonafide centimillionaire, with an estimated net worth of $176 million. He’s not so different from the billionaires who have spent vast sums of money to create a more conservative city, one that allows them to profit at the expense of regular San Franciscans.

About 70% of Chakrabarti’s campaign has been self-funded. Most of the rest — he has raised roughly $66,000 in individual contributions —  comes from donors who gave $1000 or more. They include contributions from Silicon Valley engineer Aditi Shrikumar, who donated $3,500; and tech chiefs Peter Warden and Mohammed Davoodi, who gave $7,000, a piece. Francisco Tolmasky and Ross Boucher, early employees of Chakrabarti’s startup, Stripe, contributed $3,500 and $7,000, respectively.

Many are likely tech industry acquaintances. Friends and colleagues are often part of a candidate’s fundraising list. That said, business people, like Chakrabarti’s top donors, consider campaign donations as an investment, one they expect will reap handsome benefits. Chakrabarti’s donor list looks like that of a typical conservative candidate in San Francisco. As a campaign veteran, I can tell you that most progressive campaigns are funded by small-dollar contributions supplemented with larger checks from labor unions. 

A closer look at his relationship with Congresswoman Ocasio-Cortez, who features prominently in Chakrabarti’s campaign materials, is not what it first appears to be. Their association abruptly ended in 2019 after a campaign finance investigation accused the Congresswoman’s chief of staff of financial improprieties. (A Federal Elections Commission probe uncovered no wrongdoing. According to insiders, Chakrabarti’s departure was, at least in part, due to  differences in political strategy.) It is nonetheless notable that while Chakrabarti has mentioned AOC so much, one might think he is her running mate, the New York Congresswoman has not said anything about Chakrabarti in regards to this race.

Chakrabarti’s political activity raises yet more questions. He donated more than $10,000 to Bilal Mahmood who successfully defeated progressive stalwart Dean Preston, District 5’s incumbent supervisor. A tenants’ rights attorney, Preston has arguably done more to address income inequality than any recent member of the Board of Supervisors. (Full disclosure: I was volunteer coordinator for Preston’s successful 2019 campaign.)

Further, Chakrabarti contributed $500 to Michael Lai’s unsuccessful campaign against respected labor organizer Chyanne Chen in the 2024 contest to represent District 11. Lai has been an outspoken proponent of the Network State, a strange — and authoritarian — scheme in which tech elites would exit democracy to form their own sovereign states. 

When asked about his recent political contributions, he spoke of his personal relationship with both men. He called both “progressives,” regardless that Mahmood has become part of the Board of Supervisors’ right-wing bloc. The reality is you can either be a progressive or you can give money to Lai and Mahmood, but you cannot do both. Chakrabarti is either woefully ignorant or willfully misleading San Francisco voters. Neither characteristic is suitable for a candidate representing San Francisco in the U.S. Congress.

Notably, Chakrabarti admitted he voted for Daniel Lurie, heir to the billion-dollar Levi Strauss fortune, in last year’s mayoral race — rather than progressive candidate Peskin. 

When questioned about Yimbyism — the notion that removing restrictions on development will magically result in housing at all price points — Chakrabarti’s answers were less than reassuring. Removing “obstacles” to “building” is a laudable goal, he said, sounding much like Lurie and the mayor’s right-wing supporters that include YIMBY group, GrowSF.

The recent addition of District 1 Supervisor Connie Chan to the race — a legislator with deep ties to San Francisco’s progressive movement — makes Chakrabarti’s path to victory all the more difficult. As long as he remains maddeningly contradictory, he will have a hard time positioning himself as San Francisco’s answer to Zohran Mamdani.