San Francisco — 

The final time this metropolis’s voters had somebody apart from Nancy Pelosi representing them in Congress, there have been no self-driving taxis on the streets, no AI advertisements competing for area round the tie-dye store in Haight-Ashbury. The youngest San Franciscans who may have voted then are nearing retirement age now.

“I’m not sure what came first, Pelosi or San Francisco,” California Gov. Gavin Newsom, an in depth Pelosi ally and a former mayor of the metropolis, instructed NCS not too long ago.

Now with simply weeks to go in the first spherical of the race to replace Pelosi, an iconic middle of liberalism — one which sits virtually totally inside one congressional district — is making an attempt to determine what comes subsequent.

As the Democratic Party churns over what makes a progressive and what sort of fighters its base needs, how to sort out affordability, and even whether or not to use the phrase “genocide” about Gaza, these fights are coming to a head in the metropolis Pelosi has represented in the US House since 1987.

Candidates and their advisers admit that although they’ve been getting ready for this second for years, they’re nonetheless struggling to determine it out.

They’re constructing outreach applications, explaining to voters that Pelosi isn’t operating in the June 2 nonpartisan major, discovering the proper steadiness between attacking President Donald Trump and digging in on parochial points like the enduring controversy over the Great Highway operating alongside the Pacific Coast, a stretch of which has been closed to vehicles.

Pelosi had lengthy been quiet about the race however has turn into extra express about her potential desire with time operating out earlier than June 2. Pelosi has appeared at occasions for Connie Chan, a member of the San Francisco Board of Supervisors, and talking positively about what Chan may do in Congress.

Still, a spokesperson for the former speaker factors again to a November assertion after she introduced her retirement that she didn’t plan to endorse.

“For her seat to be open is wild for the city,” Mayor Dan Lurie instructed NCS, sitting in the workplace in City Hall he received by ousting a fellow Democrat in a 2024 race that grew to become its personal referendum on whether or not conventional Democratic governance had failed the metropolis. “I don’t think we even know quite what to make of it.”

Scott Wiener, middle, meets with others at the 2026 California Democratic Party State Convention in San Francisco, Saturday, February 21, 2026.

A candidate’s lengthy ambitions

Scott Wiener has been getting ready to make one thing of it for years. Raised in New Jersey, Wiener has lived for almost 30 years in the Castro, one in every of the nation’s most outstanding homosexual neighborhoods. He began as a lawyer after which made his manner from LGBTQ political activist to the Board of Supervisors (San Francisco’s equal of a metropolis council) to representing a state Senate district that overlaps virtually solely with Pelosi’s House district.

Wiener’s years of preparations to comply with Pelosi have been about as delicate as Chonkers, the oversize sea lion that’s been exhibiting up at Fisherman’s Wharf. That got here to annoy Pelosi. Weiner acknowledged {that a} relationship that started off sturdy has turn into “a little bit strained” as he made it clear that he was going to run for her seat this yr earlier than her introduced retirement, and that he wouldn’t step apart for her daughter Christine, now operating for Wiener’s state Senate seat.

“That is what it is,” he stated.

Wiener is the type of native politician consistently popping up at occasions backwards and forwards between his district and Sacramento. Newsom, who’s staying impartial, calls him “a bit of a legend up here in terms of his ability to carry bills.” Onetime rival and now endorser Rafael Mandelman referred to as him a “transit superhero” final week for his work to cease Muni fare dodgers. But as Mandelman famous in an interview after, there are occasions when what some see as Wiener’s relentlessness comes off as stridency.

Wiener gave a practiced response to NCS about critics calling him too shut to builders, saying, “developers are the people who build housing,” which he says is a practical method to preventing one in every of the metropolis’s core crises. He says being referred to as “establishment” signifies that he has been in workplace for years, however says he has been difficult conference all that point.

That expertise can be particularly essential in Pelosi’s wake, Wiener says, together with by preventing for infrastructure cash and bringing to Washington the type of main position he has had on the state’s AI laws 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 stated. “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.”

The “someone” Wiener has in thoughts just isn’t Chan or long-shot Marie Hurabiell, however a first-time candidate operating on ties to Rep. Alexandria Ocasio-Cortez, who has had her own tense moments with Pelosi.

Saikat Chakrabarti moved to the metropolis in his 20s after which returned a number of years in the past earlier than launching what additionally began as a problem to the former House speaker.

Chakrabarti makes a degree of claiming that he doesn’t take cash from company, actual property or AI pursuits. But that’s largely due to his self-financing from the hundreds of thousands he made throughout his first stint in tech as founding engineer of the monetary companies firm Stripe.

His marketing campaign has developed a customized of providing full-time, living-wage jobs to anybody who has provided to be a dedicated volunteer, giving him a sprawling workplace in a former financial institution stuffed with a payroll of upward of 200 area organizers, door titties and telephone bankers. He has lent his marketing campaign $4.8 million to this point, in accordance to marketing campaign finance data.

Chakrabarti has spent extra per district voter than billionaire Tom Steyer is spending per voter statewide in his governor’s race.

Chakrabarti has pegged a lot of his marketing campaign to his connection to a politician from the different facet of the nation: Ocasio-Cortez. He was her campaign manager and first chief of staff, and claims credit score for a large chunk of her early success together with, he says, authoring the Green New Deal. At one discussion board, he referenced a time “when I was in Congress.”

Rep. Alexandria Ocasio-Cortez, D-N.Y., leaves a news conference in the Capitol Visitor Center after responding to negative comments by President Trump that were directed at the freshman House Democrats on Monday, July 15, 2019. Her then-chief of staff, Saikat Chakrabarti, appears at left.

Chakrabarti stated he’s additionally impressed by how US Rep. Ro Khanna of California whipped up media consideration on Jeffrey Epstein to help get a nearly unanimous vote for the bill calling for the launch of the Justice Department information on the convicted intercourse offender.

“You pick those fights and by picking those fights, you build power outside DC,” Chakrabarti instructed NCS. “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 omit is why he stopped working for Ocasio-Cortez after solely about seven months, in what has turn into a minor obsession in San Francisco political circles and impressed a automotive that follows him to some occasions with an indication studying “AOC FIRED SAIKAT.” Chakrabarti grew to become notorious for tweeting assaults on Ocasio-Cortez’s new House colleagues, together with scoffing at those who referred to as Pelosi a “legislative mastermind.”

One particular person aware of what occurred stated the freshman congresswoman struggled with whether or not to fireplace him however accepted his resignation when he provided. Chakrabarti instructed NCS it was “a planned transition out” from earlier than the tweets as a result of he had a daughter on the manner, however didn’t dispute that she accepted his resignation.

Chakrabarti is conspicuously missing an endorsement from his former boss. The identical particular person aware of what occurred stated Ocasio-Cortez wasn’t happy to discover out from media reviews that Chakrabarti was operating as an alternative of from him immediately.

He confirmed to NCS that he hadn’t instructed her in advance, explaining that he initially entered the race to problem Pelosi earlier than she introduced 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 didn’t reply to a number of requests for remark about the circumstances of Chakrabarti’s departure or why she isn’t backing him. Asked final month by a reporter from Drop Site News why she wasn’t backing him, she spoke about the position she’s making an attempt to play extra broadly in primaries and by no means talked about his title.

Beyond Ocasio-Cortez immediately, 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 personal community of like-minded House candidates round the nation.

Just final week, he had half a dozen of these candidates fly in from round the nation to be a part of his rally headlined by Hasan Piker, the streamer who has turn into a focal point in Democratic fights over his criticism of Israel. Piker has been criticized for saying the US “deserved” the September 11 assaults, a remark he has since stated he regretted making, and saying Hamas was “1,000 times better” than Israel.

While Chakrabarti says he’s typically making an attempt to localize the nationwide points on his thoughts — for instance, saying the excessive value of dwelling in the metropolis may very well be tackled by getting common healthcare or cash being spent on the conflict in Iran must be redirected to fixing the highways and public transit — a number of outstanding San Francisco politicians instructed NCS that he stays so unknown that they have been not sure how to pronounce his title.

“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 stated.

Chan just isn’t operating a lot to change the get together as to recenter on its roots. Born in Hong Kong and raised in Taiwan, she talks about so-called sanctuary metropolis protections and different work for immigrants, and she or he refers consistently to the union help she has racked up.

Connie Chan waves during the Chinese New Year Parade in San Francisco, Saturday, March 7, 2026.

“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 instructed NCS on Wednesday after one in every of the candidates’ neighborhood boards, in the woody hills at the Randall Museum.

Chan stated on stage that “San Francisco will always be the conscience of the nation and the conscience of Washington, DC.”

To her, meaning beating again the cash supporting Wiener and the cash Chakrabarti is spending on his personal marketing campaign.

“We have the most saturation of billionaires residing in this city,” she stated. “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 greater issue in the race might lie in a joke she made at the candidate discussion board: “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 considering, Pelosi is hyper-aware that San Francisco has misplaced numerous outstanding feminine representatives in latest years, together with going from each senators being girls from the Bay Area to having each senators be males from Los Angeles. Wiener and Chakrabarti additionally each introduced their campaigns in opposition to Pelosi earlier than her retirement announcement.

Plus, Pelosi likes Chan and sees a kindred political participant in the type of coalitions she’s constructing. It’s no accident, in accordance to the ally who spoke to NCS, that Pelosi has been exhibiting up at the identical occasions as Chan, together with popping by a DC fundraiser for her final month, with plans to do extra. And Chan already has the endorsement of Sen. Adam Schiff, an in depth Pelosi ally.

Asked what she thinks is happening with Pelosi, Chan smiled and stated, “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 these occasions was Thursday evening, for the Asian Pacific Council in city. According to the San Francisco Standard’s “Power Play” publication, Pelosi spoke greater than she has publicly to date, saying that for Chan to be the metropolis’s first Asian American member of Congress can be “very exciting,” and lauding her efficiency at the Washington fundraiser.

“She’d be a great member of Congress,” Pelosi stated.

The high two vote-getters will preserve this race going all the manner to November — and Pelosi is more likely to endorse then. If Chakrabarti is one in every of the candidates, that would make it extra probably she endorses the different.

In an indication of the place San Francisco politics is now, that may please each Chan’s supporters and Chakrabarti’s.



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