Saikat Chakrabarti, a former chief of staff to Rep. Alexandria Ocasio-Cortez, is trying to unseat Democratic establishment power in California’s 11th district, aiming for a House primary upset against Pelosi-backed nominee Connie Chan while fending off skeptic
SAN FRANCISCO — In a packed rally in May, Saikat Chakrabarti didn’t just talk about taking on Republicans. He urged his supporters to take on the Democratic Party that, in his view, too often refuses to move fast enough.
“Fuck Elon” and “Fuck Peter Thiel” rang out during the event. which also featured speeches from Twitch streamer Hasan Piker. former Squad member Jamaal Bowman. and a roster of progressive candidates from across the country. Chakrabarti added “Fuck the oligarchs,” and the crowd answered with loud cheers.
The anger behind the chant is part of why Chakrabarti’s insurgent push has grabbed attention in California’s 11th congressional district. The seat has long been a Democratic establishment stronghold: former House Speaker Nancy Pelosi (D-Calif.) held it for 39 years. covering portions of San Francisco. But Chakrabarti is running in the House primary not only against the broader political system he says benefits powerful interests. but also directly against the Democratic Party leadership he believes Pelosi helped build.
At the rally in May, Chakrabarti made his campaign’s intent unmistakable. “We need a new generation of leaders that won’t just stop Trump,” he said. “It’s not enough to just fight the Republicans, we have to change the Democratic Party as well.”
He says his approach means challenging insiders even when progressives are hesitant to do so. “The real difference that I’m offering is I am saying that I’m going to go in there and I’m going to challenge Democratic party leadership. ” Chakrabarti told HuffPost. He added that he would not vote for Hakeem Jeffries for Speaker and that he would support people who primary other “corporate Democrats.”.
The political math is still tight. Polls give Chakrabarti a solid chance of advancing to the general election after Tuesday’s primary. but he would still face another Democrat in the fall because California uses a top-two system. A May survey from the San Francisco Chronicle found him trailing state Sen. Scott Wiener, but in a close race with the Pelosi-endorsed Connie Chan, a progressive member of the board of supervisors.
For all the momentum from his supporters, Chakrabarti has also inherited a familiar problem for candidates trying to disrupt party norms: the left is not fully unified behind him.
Chakrabarti is promising a set of policies designed to pull the campaign into the core of progressive politics. He has said he will work on the Green New Deal and Medicare for All. In Congress, he says he plans to tax billionaires and ban stock trading.
His message has struck a nerve with some voters who feel Democrats have been unwilling to take a harder line on issues including U.S. aid to Israel, and who want lawmakers more confrontational in resisting Trump. Jocelyn Arevalo. a 27-year-old mental health counselor and Chakrabarti supporter. described her shift this way: “I traditionally have leaned Democratic. however. feeling very disappointed with some of the policies that they are unwilling to budge on.” She said she then became “intrigued.”.
But those hopes collide with questions that have dogged the candidate across his campaign—questions that don’t come only from moderates or opponents. Some progressives and local activists have also questioned whether Chakrabarti’s insurgency is matched by deep roots in San Francisco politics.
A self-described centimillionaire. Chakrabarti has poured millions of his own money into the race and has been accused by critics of trying to buy the election. According to a May filing. he has spent nearly $10 million of his own funds. used to pay for canvassers and to maintain a wide-ranging social media presence. Indivisible San Francisco organizer Peter Hosey put it bluntly: “He calls himself a centimillionaire. and that comes with pros and cons. On the one hand, he can do whatever he wants. On the other hand, he can do whatever he wants.”.
Chakrabarti counters that self-funding means he’s not beholden to corporate interests.
Even as he argues that his investment buys him independence. the campaign has also raised deeper concerns about whether Chakrabarti understands the city’s political ground game. Tim Redmond. editor of the San Francisco Bay Guardian—a left-leaning publication that endorsed Chan—said Chakrabarti has done “very little in San Francisco” and criticized what he called support for “the neoconservative and the neoliberal. the right wing of San Francisco politics.” Redmond’s adult daughter also works for Chan’s campaign.
The central line of attack from within the local left traces back to Chakrabarti’s past support for moderate candidates in local races. In 2024. Chakrabarti supported Bilal Mahmood in San Francisco’s District 5 Supervisor race over Dean Preston. who was the only democratic socialist on the panel at the time. That year, he also voted for Levi’s scion Daniel Lurie for mayor over the more progressive Aaron Peskin.
Chakrabarti says those choices weren’t inconsistent with progressive goals. He said he previously worked with Mahmood on climate change issues and favored Mahmood’s housing policies. He also pointed to later moves by Mahmood. saying Mahmood had taken positions progressives have advocated. including endorsing Proposition D. a ballot initiative that would impose additional taxes on corporations.
For Lurie, Chakrabarti said he appreciated what he described as Lurie’s “anti-establishment” campaign and that Lurie ran on big ideas. Chakrabarti said Lurie promised to set up “1,500 shelter beds in his first six months in office.”
Chakrabarti also acknowledged he hadn’t agreed with those candidates on everything. “Have I always agreed with him on everything?. Of course not,” he told HuffPost. He added: “I do wish he was more in favor of taxing the ultra rich in our city. but I also do think he’s done some good stuff around small business permit reform. around his child care plan.”.
At the May rally, Piker devoted part of his remarks to criticizing Lurie, and when Lurie’s name was mentioned, boos could be heard.
Aditya Bhumbla. a co-chair for San Francisco’s Democratic Socialists of America chapter. offered a critique that extends beyond one election cycle. Bhumbla said Chakrabarti appeared unfamiliar with “what’s going on on the ground. like the supervisor level. at the like. you know. the more local level. ” and argued that if Chakrabarti claims to represent San Franciscans in Congress. he should be aware of what’s going on inside the city.
Chakrabarti’s supporters and opponents both describe the campaign as a referendum on who gets to define progressive politics locally.
Separate from the questions raised by local activists, groups backing Scott Wiener have attempted to portray Chakrabarti as a carpetbagger who has not spent enough time in the city. Chakrabarti dismissed those critiques as “nativist in a way.”
“I. like most people in San Francisco. am not part of the local political establishment. so I can understand that coming in as an outsider. both sides of the establishment feel the need to attack me. ” Chakrabarti told HuffPost. He argued that local “gatekeepers” shouldn’t determine who is allowed to run for office. “I really don’t believe in the idea of having a politics where you have to be ordained by local political gatekeepers to wait your turn to run for office.”.
A Wiener supporter has been operating a van bearing a message attacking Chakrabarti.
The national shape of Chakrabarti’s ambitions helps explain both the enthusiasm and the friction. Before entering politics, he made millions as an engineer at the payment processing company Stripe. He left Silicon Valley to pursue politics, joining Sen. Bernie Sanders’ (I-Vt.) 2016 presidential campaign. Later, he co-founded the Justice Democrats, a group dedicated to finding and backing progressive House challengers across the country.
Chakrabarti’s philosophy has long been centered on primarying the political establishment. “We gotta primary folks,” he has previously said.
In 2018, Chakrabarti chaired Rep. Alexandria Ocasio-Cortez’s successful campaign for the House and then served as her chief of staff for seven months. During that tenure. Ocasio-Cortez rolled out the Green New Deal and joined a sit-in in Pelosi’s office alongside the Sunrise Movement to pressure incoming Speaker Nancy Pelosi on climate policy. Chakrabarti said those efforts raised the profile of climate issues and pushed 2020 presidential candidates to develop ambitious platforms.
He tied that arc to later legislation. One proposal was then-candidate Joe Biden’s Build Back Better agenda. which became the Inflation Reduction Act. legislation that included sizable investments in clean energy. Chakrabarti previously served as Rep. Alexandria Ocasio-Cortez’s first chief of staff in Congress.
At his rally, Chakrabarti said he didn’t regret ruffling feathers inside the Democratic Party. “We ruffled some feathers in the Democratic Party establishment, but you know what, I’m glad we did,” he said. “That is how we got the Democratic Party to go from wanting to do nothing on climate change to eventually passing the largest investment in climate and union jobs in history.”.
While his references to Ocasio-Cortez animate his national profile, they also hang over the race like an unresolved question. Ocasio-Cortez has yet to endorse him. Chakrabarti’s opponents claim the absence shows the two ended their relationship on bad terms. Ocasio-Cortez, who is described in the piece as a potential 2028 presidential candidate, has dodged questions about the relationship.
Chakrabarti says he has a “good relationship” with Ocasio-Cortez.
He also says he intends to become more combative if elected. He has said he will use tools like a discharge petition to try to force votes on policies such as banning Congressional stock trading. He has also talked about strategically organizing more progressive challengers once he’s there.
At the May rally. Piker framed the fight as one that must include Democrats who he called “collaborators.” “We know that the Republican Party is a reactionary scourge in this country. we know they’re fascist. we know they’re racist. we know they’re warmongerers. But we say no more to the Democratic collaborators, too,” Piker said.
Those lines reflect a broader ambition in Chakrabarti’s campaign: to build a pipeline of progressive insurgents, not just to win one seat.
For supporters, the House race echoes their earlier experience with insurgent politics. Arevalo said she recognized a similar message in Chakrabarti’s campaign and earlier efforts by Zohran Mamdani when Mamdani was running. Chakrabarti has framed his run as part of a larger national movement that could one day include dozens of progressive challengers.
At the May rally. he boosted a group of progressive candidates running for offices in New York City. Los Angeles. and Denver: Darializa Avila Chevalier. Angela Gonzales-Torres. and Melat Kiros. He said. “This is the culmination of that movement that started with Bernie in 2016. and I’ve seen it grow and grow and grow.”.
Chakrabarti also argued that San Francisco has repeatedly pushed the country forward, citing Wong Kim Ark’s fight for birthright citizenship and trans women’s demonstrations against police violence in the Tenderloin. Voters, he said, have a chance to do it again.
“Every single time the country were to move, San Francisco has pushed, and right now, we need San Francisco to push again today,” Chakrabarti said.
Still. even in a city that has become a symbol of progressive change. Chakrabarti’s biggest test may be whether the local left can turn excitement into unity—especially when his own history. his self-funded campaign. and the unresolved question of whether Ocasio-Cortez will endorse him continue to leave part of the coalition uneasy.
As Tuesday’s primary approaches, Chakrabarti’s supporters see a candidate ready to fight both parties. His critics—some from within progressive ranks—see a national figure whose insurgency may not fully match the local politics he’s asking to represent.
Saikat Chakrabarti Nancy Pelosi Connie Chan Scott Wiener Ocasio-Cortez Justice Democrats Green New Deal Medicare for All Inflation Reduction Act San Francisco politics California 11th district primary