San Francisco – California's 11th congressional district has long been a bastion of Democratic establishment power, held by former House Speaker Nancy Pelosi for 39 years. Now, a leading candidate to replace her is running directly against the system she helped build. Saikat Chakrabarti, a former chief of staff for Rep. Alexandria Ocasio-Cortez, is waging an insurgent primary campaign aimed at both President Donald Trump and the Democratic establishment.
A New Generation of Leadership
“We need a new generation of leaders that won’t just stop Trump,” Chakrabarti said at a May rally. “It’s not enough to just fight the Republicans, we have to change the Democratic Party as well.” While many progressives are running for deep-blue House seats on anti-establishment platforms, Chakrabarti goes further. He promises to challenge Democratic leadership and primary corporate Democrats, unlike some Squad members who have been reluctant to endorse primary challengers to sitting members.
“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.”
Primary Prospects
Polls give Chakrabarti a solid chance of advancing to the general election after Tuesday’s primary, though he would still compete against another Democrat in the 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 Pelosi-endorsed Connie Chan for the second spot.
Chakrabarti has poured millions of his own money into the race, drawing criticism for trying to buy the election. He has also faced scrutiny for backing moderates in local races and for insufficient ties to district communities. Despite this, his message resonates with voters weary of Democrats’ unwillingness to take stronger stances on issues like Israel aid and Trump opposition.
Building a Movement
Chakrabarti left a career at Stripe to pursue politics, joining Bernie Sanders’ 2016 campaign and co-founding Justice Democrats. He chaired Ocasio-Cortez’s 2018 campaign and served as her chief of staff, helping launch the Green New Deal. His confrontational approach has drawn both praise and criticism.
“We ruffled some feathers in the Democratic Party establishment, but you know what, I’m glad we did,” Chakrabarti 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.”
Local Controversies
Chakrabarti’s support for moderate candidates in local races has sparked backlash. In 2024, he backed Bilal Mahmood over democratic socialist Dean Preston for supervisor and voted for Levi’s heir Daniel Lurie for mayor over progressive Aaron Peskin. He defends these choices on policy grounds, citing housing and climate issues.
“Have I always agreed with him on everything? Of course not,” Chakrabarti said. “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.” Critics question his commitment to local progressive coalitions. “I think there does seem to be a little bit of unfamiliarity of what’s going on on the ground,” said Aditya Bhumbla of San Francisco’s DSA chapter.
Self-Funding and Outsider Status
Chakrabarti has spent nearly $10 million of his own money, fueling attacks from opponents. He argues self-funding frees him from corporate interests. “I, like most people in San Francisco, am not part of the local political establishment,” he said. “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.”
For supporters, Chakrabarti represents a national movement. “This is the culmination of that movement that started with Bernie in 2016, and I’ve seen it grow and grow and grow,” he said at the rally, also boosting progressive candidates from other cities.
Chakrabarti argues San Francisco has historically pushed the country forward, from birthright citizenship to trans rights. “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.
