LOADINGERROR LOADING
SAN FRANCISCO – California’s 11th congressional district has long been a center of Democratic establishment power. Former House Speaker Nancy Pelosi (D-Calif.) has held the seat, which covers portions of San Francisco, for 39 years.
One of the leading candidates to replace Pelosi, however, is running directly against the system the longtime congresswoman played such a central role in building. Saikat Chakrabarti, a former chief of staff for Rep. Alexandria Ocasio-Cortez (D-N.Y.), is making an insurgent push in the House primary, with a campaign aimed as much at Pelosi and her ilk as it is at President Donald Trump.
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“We need a new generation of leaders that won’t just stop Trump,” Chakrabarti said at a rally in May. “It’s not enough to just fight the Republicans, we have to change the Democratic Party as well.”
While there are plenty of progressives running for deep-blue U.S. House seats on anti-establishment platforms, Chakrabarti seems to be going a step further. Some members of the Squad, including Ocasio-Cortez, have been squeamish about endorsing primary challengers to sitting members. Chakrabarti is promising he will not share their reluctance.
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“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. “I’m not going to vote for Hakeem Jeffries for Speaker. I’m going to support people who primary challenge other corporate Democrats.”
Polls give Chakrabarti a solid chance of advancing to the general election after Tuesday’s primary, though he’d still have to compete against another Democrat this fall due to California’s 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 the second spot.
But as Chakrabarti works to change the party, he has run headfirst into many of the criticisms progressives often levy against moderates. A self-described centimillionaire, he’s poured millions of his own money into the race and been accused of trying to buy the election. Chakrabarti has also faced scrutiny for siding with moderates in key local races. And he’s been attacked for insufficient ties to the district’s communities. A candidate some see as a national progressive hero, he’s struggled to unite parts of the local left.
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At the rally in May, none of that seemed to matter. Shouts of “Fuck Elon” and “Fuck Peter Thiel” could be heard during the event, which also featured speeches from Twitch streamer Hasan Piker, former Squad member Jamaal Bowman, and a string of progressive candidates from across the country.
“Fuck the oligarchs,” Chakrabarti added at one point to loud cheers.
Chakrabati is promising to work on the Green New Deal and Medicare for All, and said he plans to tax billionaires and ban stock trading in Congress. His message is resonating with voters who’ve become weary of Democrats’ unwillingness to take a stronger stance on issues like U.S. aid to Israel, and who think that lawmakers should be more combative in their fight against Trump.
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“I traditionally have leaned Democratic, however, feeling very disappointed with some of the policies that they are unwilling to budge on,” said Jocelyn Arevalo, a 27-year-old mental health counselor and Chakrabarti supporter. “I was like, wait, I’m intrigued.”
“We Gotta Primary Folks”
Chakrabarti has encouraged Democrats to take a more confrontational approach for years.
After making millions as an engineer at the payment processing company Stripe, Chakrabarti left Silicon Valley to pursue politics. He joined Sen. Bernie Sanders’ (I-Vt.) 2016 presidential campaign, then co-founded the Justice Democrats, a group dedicated to finding and backing progressive House challengers across the country.
“We gotta primary folks,” Chakrabarti has previously said.
In 2018, Chakrabarti chaired Ocasio-Cortez’s successful campaign for the House and served as her chief of staff for seven months. During his tenure, Ocasio-Cortez rolled out the Green New Deal and joined a sit-in in Pelosi’s office alongside the Sunrise Movement to pressure the incoming Speaker on climate policy. Chakrabarti noted that these efforts raised the profile of climate issues and compelled 2020 presidential candidates to put out ambitious platforms. One of those proposals was former President Joe Biden’s Build Back Better agenda, which became the Inflation Reduction Act, legislation that included sizable investments in clean energy.
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“We ruffled some feathers in the Democratic Party establishment, but you know what, I’m glad we did,” Chakrabarti said at his rally. “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 serving as Ocasio-Cortez’s chief of staff, Chakrabarti wasn’t shy about criticizing centrist lawmakers and Democratic leadership on social media. In one post that mentioned Rep. Sharice Davids (D-Kan.) by name, he described moderates’ support for border funding as enabling a “racist system,” which drew a rebuke from the Democratic caucus’ Twitter account, then managed by Jeffries’s office.
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“He was chief of staff with AOC, so he understands how the Capitol works,” says David Cantù, 24, a Chakrabarti supporter and San Francisco State University student who volunteers with the campaign.
But hanging over his invocations of Ocasio-Cortez is the fact that she has yet to endorse him, with his opponents claiming it shows the two ended their relationship on bad terms. The congresswoman, a potential 2028 presidential candidate, has dodged questions on the matter. He has said the two have a “good relationship.”
Chakrabarti has indicated that he intends to employ more combative tactics if he takes office. He’s said he’ll use tools like a discharge petition to try to force a vote on policies such as banning Congressional stock trading, and he’s talked about strategically organizing more progressive challengers once he’s there.
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“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 at the May rally.
“Local Political Gatekeepers”
While Chakrabarti’s federal stances have largely been welcomed by local progressives, some have questioned his past support for moderate candidates in local races.
“I’ve met with Saikat, and he’s a very personable guy, and I agree with a lot of the things that he says about national politics. He has done very little in San Francisco, and the little that he’s done in San Francisco that we can judge him on…is to give money to the neoconservative and the neoliberal, the right wing of San Francisco politics,” said Tim Redmond, editor of the San Francisco Bay Guardian, a left-leaning publication that has endorsed Chan. (Redmond’s adult daughter also works for Chan’s campaign.)
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In 2024, Chakrabarti supported Bilal Mahmood in San Francisco’s District 5 Supervisor race over Dean Preston, 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 has pointed to specific policy reasons for his past support. He said he previously worked with Mahmood on climate change issues and favored his housing policies. Chakrabarti also noted that Mahmood had since taken positions that progressives have advocated, such as endorsing Proposition D, a ballot initiative that would impose additional taxes on corporations. He said he appreciated the “anti-establishment” campaign that Lurie ran as a candidate and that he’d committed to put forth some big ideas, including “setting up 1,500 shelter beds in his first six months in office.”
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“Have I always agreed with him on everything? Of course not,” Chakrabarti told HuffPost. “You know, 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 spent part of his remarks criticizing Lurie, who received boos when his name was mentioned.
For some political observers, Chakrabarti’s past positions have raised questions about his dedication to progressive coalitions in the city and his familiarity with local dynamics.
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“I think there does seem to be a little bit of unfamiliarity of what’s going on on the ground, like the supervisor level, at the like, you know, the more local level, and if somebody is claiming to represent us for Congress, I think they should be aware of what’s what’s going on inside the city,” said Aditya Bhumbla, a co-chair for San Francisco’s Democratic Socialists of America chapter, which is neutral and has not made an endorsement in this race.
Separately, groups supporting Wiener have attempted to attack the political adviser as a carpetbagger who hasn’t spent sufficient time in the city, critiques that Chakrabarti dismissed 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. “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.”
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Chakrabarti has self-funded much of his campaign, fueling broadsides from his opponents as well. According to a May filing, he has spent nearly $10 million of his own funds, which were used to pay for canvassers and a wide-ranging social media presence.
“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,” said Indivisible San Francisco organizer Peter Hosey. (Indivisible SF doesn’t endorse in primary races and is also neutral in this contest.)
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Chakrabarti emphasizes that self-funding has meant he’s not beholden to corporate interests.
The critiques he’s faced and the presence of another progressive candidate in the race have, however, left local voters split.
“The Culmination Of That Movement”
For Chakrabarti’s supporters, the House contest has familiar echoes.
“I just saw his videos around the time Zohran Mamdani was also campaigning, and it felt like the closest thing we had to a similar message,” said Arevalo.
Chakrabarti has framed his run as one part of a larger national movement that could one day include dozens of progressive challengers in Congress. At the May rally, Chakrabarti not only made a case for his own bid, he also boosted Darializa Avila Chevalier, Angela Gonzales-Torres and Melat Kiros, who are all progressive candidates running for offices in New York City, Los Angeles and Denver.
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“Every single time the country were to move, San Francisco has pushed, and right now, we need San Francisco to push again today,” he said.
