Democrats’ internal fights sway the race to succeed Nancy Pelosi in San Francisco
By Edward-Isaac Dovere, CNN
San Francisco (CNN) — The last time this city’s voters had someone other than Nancy Pelosi representing them in Congress, there were no self-driving taxis on the streets, no AI ads competing for space around the tie-dye shop in Haight-Ashbury. The youngest San Franciscans who could have voted then are nearing retirement age now.
“I’m not sure what came first, Pelosi or San Francisco,” California Gov. Gavin Newsom, a close Pelosi ally and a former mayor of the city, told CNN recently.
Now with just weeks to go in the first round of the race to replace Pelosi, an iconic center of liberalism — one that sits almost fully within one congressional district — is trying to figure out what comes next.
As the Democratic Party churns over what makes a progressive and what kind of fighters its base wants, how to tackle affordability, or even whether to use the word “genocide” about Gaza, those fights are coming to a head in the city Pelosi has represented in the US House since 1987.
Candidates and their advisers admit that though they’ve been preparing for this moment for years, they’re still struggling to figure it out.
They’re building outreach programs, explaining to voters that Pelosi isn’t running in the June 2 nonpartisan primary, finding the right balance between attacking President Donald Trump and digging in on parochial issues like the enduring controversy over the Great Highway running along the Pacific Coast, a stretch of which has been closed to cars.
Pelosi had long been quiet about the race but has become more explicit about her potential preference with time running out before June 2. Pelosi has appeared at events for Connie Chan, a member of the San Francisco Board of Supervisors, and speaking positively about what Chan could do in Congress.
Still, a spokesperson for the former speaker points back to a November statement after she announced her retirement that she did not plan to endorse.
“For her seat to be open is wild for the city,” Mayor Dan Lurie told CNN, sitting in the office in City Hall he won by ousting a fellow Democrat in a 2024 race that became its own referendum on whether traditional Democratic governance had failed the city. “I don’t think we even know quite what to make of it.”
A candidate’s long ambitions
Scott Wiener has been preparing to make something of it for years. Raised in New Jersey, Wiener has lived for nearly 30 years in the Castro, one of the nation’s most prominent gay neighborhoods. He started as a lawyer and then made his way from LGBTQ political activist to the Board of Supervisors (San Francisco’s equivalent of a city council) to representing a state Senate district that overlaps almost entirely with Pelosi’s House district.
Wiener’s years of preparations to follow Pelosi were about as subtle as Chonkers, the oversize sea lion that’s been showing up at Fisherman’s Wharf. That came to annoy Pelosi. Weiner acknowledged that a relationship that started out strong has become “a little bit strained” as he made it clear that he was going to run for her seat this year before her announced retirement, and that he wouldn’t step aside for her daughter Christine, now running for Wiener’s state Senate seat.
“That is what it is,” he said.
Wiener is the kind of local politician constantly popping up at events back and forth between his district and Sacramento. Newsom, who is staying neutral, calls him “a bit of a legend up here in terms of his ability to carry bills.” Onetime rival and now endorser Rafael Mandelman called him a “transit superhero” last week for his work to stop Muni fare dodgers. But as Mandelman noted in an interview after, there are times when what some see as Wiener’s relentlessness comes off as stridency.
Wiener gave a practiced response to CNN about critics calling him too close to developers, saying, “developers are the people who build housing,” which he says is a pragmatic approach to fighting one of the city’s core crises. He says being called “establishment” means that he has been in office for years, but says he has been challenging convention all that time.
That experience would be especially important in Pelosi’s wake, Wiener says, including by fighting for infrastructure money and bringing to Washington the kind of leading role he has had on the state’s AI regulations with a Bay Area mentality.
“People may not know all the details, but they generally understand that Nancy has delivered in a huge way for San Francisco,” he said. “And San Franciscans don’t want someone who’s just going to like be all hot air with lots of hot takes and just having opinions.”
A self-funded movement
The “someone” Wiener has in mind is not Chan or long-shot Marie Hurabiell, but a first-time candidate running on ties to Rep. Alexandria Ocasio-Cortez, who has had her own tense moments with Pelosi.
Saikat Chakrabarti moved to the city in his 20s and then returned several years ago before launching what also started as a challenge to the former House speaker.
Chakrabarti makes a point of saying that he doesn’t take money from corporate, real estate or AI interests. But that’s largely due to his self-financing from the millions he made during his first stint in tech as founding engineer of the financial services company Stripe.
His campaign has developed a custom of offering full-time, living-wage jobs to anyone who has offered to be a committed volunteer, giving him a sprawling office in a former bank filled with a payroll of upward of 200 field organizers, door knockers and phone bankers. He has lent his campaign $4.8 million so far, according to campaign finance records.
Chakrabarti has spent more per district voter than billionaire Tom Steyer is spending per voter statewide in his governor’s race.
Chakrabarti has pegged much of his campaign to his connection to a politician from the other side of the country: Ocasio-Cortez. He was her campaign manager and first chief of staff, and claims credit for a sizable chunk of her early success including, he says, authoring the Green New Deal. At one forum, he referenced a time “when I was in Congress.”
Chakrabarti said he’s also inspired by how US Rep. Ro Khanna of California whipped up media attention on Jeffrey Epstein to help get a nearly unanimous vote for the bill calling for the release of the Justice Department files on the convicted sex offender.
“You pick those fights and by picking those fights, you build power outside DC,” Chakrabarti told CNN. “And then you use that lever of power outside as leverage on the inside to get stuff done. And that’s sort of what I saw AOC do in her first term.”
What Chakrabarti tends to leave out is why he stopped working for Ocasio-Cortez after only about seven months, in what has become a minor obsession in San Francisco political circles and inspired a car that follows him to some events with a sign reading “AOC FIRED SAIKAT.” Chakrabarti became infamous for tweeting attacks on Ocasio-Cortez’s new House colleagues, including scoffing at those who called Pelosi a “legislative mastermind.”
One person familiar with what happened said the freshman congresswoman struggled with whether to fire him but accepted his resignation when he offered. Chakrabarti told CNN it was “a planned transition out” from before the tweets because he had a daughter on the way, but did not dispute that she accepted his resignation.
Chakrabarti is conspicuously lacking an endorsement from his former boss. The same person familiar with what happened said Ocasio-Cortez wasn’t pleased to find out from media reports that Chakrabarti was running instead of from him directly.
He confirmed to CNN that he hadn’t told her in advance, explaining that he initially entered the race to challenge Pelosi before she announced her retirement and that “I didn’t want her to be in a weird spot where she’s asked about, you know, someone stepping up against Nancy Pelosi.”
A spokesperson for Ocasio-Cortez did not respond to several requests for comment about the circumstances of Chakrabarti’s departure or why she isn’t backing him. Asked last month by a reporter from Drop Site News why she wasn’t backing him, she spoke about the role she’s trying to play more broadly in primaries and never mentioned his name.
Beyond Ocasio-Cortez directly, Chakrabarti says he’s channeling the spirit of the work he did with the group Justice Democrats, a supporter in her first race, to create his own network of like-minded House candidates around the country.
Just last week, he had half a dozen of those candidates fly in from around the country to join his rally headlined by Hasan Piker, the streamer who has become a focal point in Democratic fights over his criticism of Israel. Piker has been criticized for saying the US “deserved” the September 11 attacks, a comment he has since said he regretted making, and saying Hamas was “1,000 times better” than Israel.
While Chakrabarti says he’s often trying to localize the national issues on his mind — for example, saying the high cost of living in the city could be tackled by getting universal healthcare or money being spent on the war in Iran should be redirected to fixing the highways and public transit — several prominent San Francisco politicians told CNN that he remains so unknown that they were unsure how to pronounce his name.
“Tell them that my name is pronounced ‘Shway-kat’ and they should learn that. They can ask me. I’m very friendly about it,” he said.
A supervisor with an unofficial Pelosi nod
Chan is not running so much to change the party as to recenter on its roots. Born in Hong Kong and raised in Taiwan, she talks about so-called sanctuary city protections and other work for immigrants, and she refers constantly to the union support she has racked up.
“This is a moment for us to decide: Is it going to someone like me, who’s been a first-generation immigrant and Chinese American woman, and has been endorsed by the working people, the labor movement, or are they going to go with a corporate Democrat that have been bankrolled by a billionaire, or a tech bro that’s been helicoptered into San Francisco?” Chan told CNN on Wednesday after one of the candidates’ community forums, in the woody hills at the Randall Museum.
Chan said on stage that “San Francisco will always be the conscience of the nation and the conscience of Washington, DC.”
To her, that means beating back the money supporting Wiener and the money Chakrabarti is spending on his own campaign.
“We have the most saturation of billionaires residing in this city,” she said. “And so can we actually fight and beat the billionaires and their PACs in this very city and send the representative for the working people from here to Washington, DC?”
But for Chan, the bigger factor in the race may lie in a joke she made at the candidate forum: “The biggest challenge I face if I’m elected is I am not Speaker Emerita Nancy Pelosi.”
According to an ally who spoke anonymously to share her thinking, Pelosi is hyper-aware that San Francisco has lost a number of prominent female representatives in recent years, including going from both senators being women from the Bay Area to having both senators be men from Los Angeles. Wiener and Chakrabarti also both announced their campaigns against Pelosi before her retirement announcement.
Plus, Pelosi likes Chan and sees a kindred political player in the kind of coalitions she’s building. It’s no accident, according to the ally who spoke to CNN, that Pelosi has been showing up at the same events as Chan, including popping by a DC fundraiser for her last month, with plans to do more. And Chan already has the endorsement of Sen. Adam Schiff, a close Pelosi ally.
Asked what she thinks is going on with Pelosi, Chan smiled and said, “How about this: I would say that I am confident that I’m the only candidate in the position to earn her endorsement.”
One of those events was Thursday night, for the Asian Pacific Council in town. According to the San Francisco Standard’s “Power Play” newsletter, Pelosi spoke more than she has publicly to date, saying that for Chan to be the city’s first Asian American member of Congress would be “very exciting,” and lauding her performance at the Washington fundraiser.
“She’d be a great member of Congress,” Pelosi said.
The top two vote-getters will keep this race going all the way to November — and Pelosi is much more likely to endorse then. If Chakrabarti is one of the candidates, that could make it more likely she endorses the other.
In a sign of where San Francisco politics is now, that might please both Chan’s supporters and Chakrabarti’s.
The-CNN-Wire
™ & © 2026 Cable News Network, Inc., a Warner Bros. Discovery Company. All rights reserved.
