Is SF congressional candidate a progressive champion or ‘impostor’?

San Francisco congressional candidate Saikat Chakrabarti was largely unknown on the city’s political scene when he launched his campaign for the House seat held by Rep. Nancy Pelosi for decades. 

While he spent seven months in Congress as chief of staff to Rep. Alexandria Ocasio-Cortez, D-N.Y., Chakrabarti has barely waded into San Francisco politics in the 17 years since he first moved to the city.

To Chakrabarti and his supporters, his scant experience in local governance isn’t a weakness — it’s an asset in his campaign as an outsider who wants to push the Democratic Party in a bolder, more progressive direction. But as the race to succeed Pelosi intensifies ahead of the June 2 primary, Chakrabarti’s critics have repeatedly cast him as unqualified.

Donors supporting state Sen. Scott Wiener, the presumed front-runner, paid for mailers that describe Chakrabarti as barely connected to San Francisco. One Wiener supporter was even linked to a mysterious van that made a similar argument in a more provocative fashion. 

But it’s not just Wiener’s fans who are making that argument. Some local progressives and labor union leaders who support another major candidate, Supervisor Connie Chan, are also deeply skeptical about Chakrabarti, a wealthy former tech engineer who has little history of backing the local candidates and causes they support. 

Chakrabarti is largely self-funding his campaign, but his fundraising reflects that he is getting a lot of support from outside San Francisco:  66% of his donors through March were from outside California. Additionally, Politico previously reported that Chakrabarti voted once in San Francisco in 2010 — and did not cast a ballot in the city again for a decade. He spent several of those years living in other places.

“He’s a total imposter,” said Aaron Peskin, a Chan backer who was a longtime member of the Board of Supervisors. “He’s very interested in being an elected official, but he has … no track record in … San Francisco that I’m aware of.”

Allies of Chakrabarti have a far different view. 

In Chakrabarti, supporters see a fighter who is willing to take strong stances on issues such as Israel’s war in Gaza, healthcare and wealth inequality. Chakrabarti has promised to support an arms embargo on Israel, push to make Medicare available to all Americans, and back tax increases on the country’s richest residents — including himself. He has also said he will challenge party leadership when necessary to advance his goals, including by voting to oust Rep. Hakeem Jeffries, D-N.Y. as the House Democrats’ leader. 

“The system is broken. The establishment has been failing us,” former San Francisco Democratic Party Chair Honey Mahogany said at a recent Chakrabarti campaign event. “We need new blood. We need a new generation of leaders … who are not in the pockets of the special interests.”

Chakrabarti has blasted the influence of deep-pocketed tech donors who have lined up behind Wiener, his main opponent. But Chakrabarti’s campaign has been bankrolled heavily by his own wealth, which he accumulated by “winning the startup lottery” in his early years in San Francisco. 

He moved to the city in 2009, when he was 23. A few years later, he became one of the earliest employees at Stripe, the payment processing company now valued at $159 billion. Stripe’s success made Chakrabarti a centimillionaire for earnings above $100 million, and he has spent about $5 million of his own money on the race so far. 

He told the Chronicle that his time at Stripe also fueled a political awakening.

“I was seeing the cost-of-living crisis going crazy around me,” Chakrabarti said of his early years in San Francisco. “I started to realize I wasn’t working on the actual problems that were facing people in tech. So I quit.”

After leaving the tech industry, Chakrabarti got involved in federal politics, starting with the 2016 presidential campaign of Sen. Bernie Sanders. He subsequently co-founded two political groups, helmed Ocasio-Cortez’s successful 2018 House campaign and became her first chief of staff once she was elected.

His time on the East Coast has been a major source of scrutiny in his House campaign. 

In 2018, he purchased a $1.6 million home in Gaithersburg, Md. — and signed a deed in which he listed that house as his primary residence, according to a November report from the San Francisco Standard. He has said he bought that house for his parents and described the primary residence declaration as a mistake that he has since corrected.

Nonetheless, the Maryland house became a launching pad for criticism from Wiener, who referenced the Standard story in a March video attacking Chakrabarti. Abundant Future, a super PAC that supports Wiener, has gone even further, sending multiple mailers that cast Chakrabarti as a carpetbagger.  

Chakrabarti has fired back, accusing Wiener of misrepresenting the details of the Maryland home purchase and calling the attacks on his San Francisco residency as “nativist in a way.” 

While he made a name for himself as a progressive on the national level, Chakrabarti’s limited track record with local candidates has been more politically diverse.

Chakrabarti supported Supervisor Bilal Mahmood’s successful 2024 bid to unseat Dean Preston, a democratic socialist who had been the most left-leaning member of the Board of Supervisors. He also backed another moderate supervisor candidate in a different district and voted for moderate Mayor Daniel Lurie.

Chakrabarti told the Chronicle that his electoral preferences haven’t always aligned neatly with the city’s political camps. He said he previously supported Preston but felt “lined up a bit more” on housing policy with Mahmood, who favored more aggressive measures to build housing for all income levels. He said he voted for Lurie because he believes that “the tribal politics in this city is one of the reasons for its dysfunction” and he thought Lurie could change that.

Chakrabarti also noted that he has supported some local progressive candidates, including Chesa Boudin’s successful bid for San Francisco district attorney in 2019 before his recall in 2022. 

Still, no sitting elected official in San Francisco has endorsed Chakrabarti’s campaign. None of the city’s labor unions has endorsed him, either — which is rare for a leading progressive candidate. Many labor groups have rallied around Chan’s bid, though some have backed Wiener.

Mike Casey, a Chan supporter and president of the San Francisco Labor Council, said the supervisor had consistently backed union causes throughout her time in public office, but he couldn’t say the same about Chakrabarti.

“He doesn’t know our issues. He hasn’t been there when we’ve been fighting to raise the minimum wage or make sure that low-wage workers get healthcare,” Casey said. “How can you claim the mantle of being a progressive if you don’t even have a strong alliance with the traditional progressive organizations and institutions like organized labor?”

Eric Jaye, a political consultant who estimated he has been involved with more than 100 local campaigns, said Chakrabarti’s thin list of local endorsements could hurt him with voters. 

“I don’t think his money erases all of that,” Jaye said. “San Francisco politics tends to be highly reliant on validation from trusted sources. … It’s still a place where voters would like to know that somebody that they know and trust has vetted you.”

Chakrabarti isn’t worried. 

“I’m running as the outsider to the political establishment — that means it’s going to be hard for me, in a primary like this, to get local endorsements,” he told the Chronicle. “That’s not going to stop me from being a pro-labor candidate. … Going into November, I do hope to earn the endorsement of local progressive and union groups.”

While the local progressive establishment has largely shied away from backing Chakbarti during the primary, so has his former boss, Ocasio-Cortez, a national progressive superstar. Chakrabarti told the Chronicle he has “a good relationship” with Ocasio-Cortez and hopes to earn her backing in the future.

Yet Chakrabarti has had little difficulty spreading the word about his candidacy, especially online. 

One of his advertisements, in which he touts his national political experience while walking through Dolores Park, has more than 1 million views on YouTube. He is a prolific poster on social media sites: On Instagram, he has more followers than Wiener and Chan combined. 

Chakrabarti has also paid handsomely to amass an army of paid field organizers who his campaign says have knocked on hundreds of thousands of doors — a task other campaigns typically rely on volunteers to complete.

“I feel like his presence is really strong,” said San Francisco resident Risa Takenaka, 28, who attended a recent Chakrabarti campaign event and said she was inclined to support his campaign. 

Takenaka was among a large crowd of people who recently packed into a Castro storefront that Chakrabarti has turned into his second campaign office in the city. She said she was unmoved by the attacks she has seen against Chakrabarti.

But some other attendees told the Chronicle they were thinking about Chakrabarti’s local track record as they contemplated whether to back him.

Don Bliss, a 66-year old San Francisco resident, called Chakrabarti’s decision to support some moderate local candidates in the 2024 election cycle as “rather disturbing for a progressive.”

“I’ve questioned his local bona fides,” Bliss said. “I don’t think that the argument is strong enough to not vote for him, because he does have significant local connections … but I am weighing that as part of my decision.”

Hafeth “Omar” Mansouri, the manager of Key Food Market on Fillmore Street — around the corner from the first San Francisco home Chakrabarti bought 13 years ago — said he’s known the candidate for years and runs into him on the street regularly. 

Mansouri, 45, has grown into a strong supporter of Chakrabarti’s political efforts, recently appearing in a social media video with the candidate and Hasan Piker, a popular leftist streamer with a history of controversial comments.

“What he says and what he does — it resonates with me,” Mansouri told the Chronicle, citing Chakrabarti’s stances on several issues, including the war in Gaza. “He’s progressive.”

In his interview with the Chronicle, Chakrabarti stressed that he has considered San Francisco home for much of his adult life. He also made it clear that he thinks the national focus of his past political work can help him deliver for local residents.

“I really believe that the issues San Francisco is facing — whether it’s the cost of living crisis or  the homelessness crisis — these are the issues that we’re facing hardest, but they are national issues,” he said. “We have to do these big, structural changes nationally to fix these (problems) for our communities right here.”