- By Adam Shanks | Examiner staff writer
- Nov 6, 2025 (SFExamner.com)
The exit of a political legend has opened the door for a new political discourse — or a free-for-all fracas — in San Francisco for the first time in nearly 40 years.
Rep. Nancy Pelosi’s decision not to run for reelection, announced Thursday, will allow San Francisco to openly debate how its representative — and the Democratic Party — should approach this unprecedented moment in American politics and democracy in the 2026 election.
Since Pelosi was first elected to Congress in a special election in 1987, tech bubbles have ballooned and burst, the Embarcadero Freeway was torn down and whole new neighborhoods have sprouted up. The City is different, and so is the country — and in many ways, both are internally divided.
Two prominent candidates have already lined up to fill Pelosi’s seat, and more are likely to join, each offering a different path forward.
Saikat Chakrabarti is a millionaire thanks to his participation in San Francisco’s last big tech wave, during the quaint days before artificial intelligence was the investment de rigueur. His wealth comes from tech, but has hitched his political wagon to stars such as U.S. Sen. Bernie Sanders of Vermont and U.S. Rep. Alexandria Ocasio-Cortez of New York, both of whom he helped campaign.
In 2026, Chakrabarti will test whether voters trust a millionaire to stick it to the billionaires — if such a message even resonates here — and solve an affordability crisis while possibly stretching the definition of a “grassroots” campaign.
State Sen. Scott Wiener has made a name for himself in San Francisco by being an capital-A “Abundance”-style Democrat who champions housing development. But on the national stage, he has earned recognition and a fair share of Fox News hate for being a fiercely proud gay man and an online opponent of the MAGA crowd. Can Wiener be both versions of himself in a successful congressional run?
Speculation also has run rampant that San Francisco Supervisor Connie Chan could enter the mix. Chan, who represents a district that includes the Richmond neighborhood, has positioned herself as an adult-in-the-room presence on the Board of Supervisors as chair its Budget Committee amid particularly calamitous budget cycles.
Politically, Chan has proven capable of marshaling the power of organized labor to help her win reelection. Though commonly labeled as a progressive, she’s worked closely with moderate Mayor Daniel Lurie.
No matter who’s running, San Francisco voters will have to ask themselves what’s most important to them in a congressional representative. Inherently local issues — such as the increasingly hellish process of finding a livable apartment — are likely to be top of mind for many.
But on the national level, democratic norms are being upended left and right under President Donald Trump, and the stakes couldn’t possibly be higher. Democrats — and Pelosi in particular — have faced criticism for failing to have a clear counterstrategy in place when Trump and the Republican Party surged back to power in 2024.
The race could shape up to be a referendum on Pelosi’s leadership, particularly under Trump’s two terms and amid increasing pressure within the Democratic Party to shift politically leftward.
For what it’s worth, Trump reacted to the news of her retirement by saying “it is a great thing for America” and calling her a “highly overrated politician.”
Candidates will have to weigh how much they want to pitch themselves as a continuation of a representative who was undeniably popular in San Francisco — she never faced a serious challenge over 20 terms in office — but immensely polarizing on the national stage.
Chakrabarti, who has never run for office himself before, was particularly critical of Pelosi, calling on her to make way for a new generation of leadership and calling for a leftward shift by the Democratic Party. Wiener had long praised Pelosi and pledged to wait until she retired to seek the position — only to announce his candidacy before she officially bowed out.
The difference between the two candidates was evident in videos they posted to social media after Pelosi’s announcement. Chakrabarti effectively thanked Pelosi for getting out of the way and quickly offered himself as a leader who “won’t just manage a broken system” but rebuild it. Wiener, on the other hand, rattled off an array of Pelosi’s accomplishments, including the fight she pledged to wage against AIDS immediately upon taking the seat in 1987.
“She was sticking up for people like me, for kids like me, for gay men like me, and I and so many others will be eternally grateful for her fight and for her leadership,” Wiener said.
Particularly since giving up Democratic leadership in the House in 2022, Pelosi preferred a diminished public role, while still orchestrating behind the scenes. In 2024, she reportedly played a key role in urging President Joe Biden to step aside in the contest against Trump. And in the recent campaign for Proposition 50, Pelosi was reportedly pivotal from the jump in fundraising, but left it to party leaders such as Gov. Gavin Newsom to give the stump speeches and appear in advertisements.
Such tact was emblematic of Pelosi’s commitment to the party.
But what will Pelosi do now that she’s not — or at least not directly — serving the party and San Francisco? There’s ample speculation that should Chan run, Pelosi could throw her still-ample political muscle behind the Richmond-district supervisor.
Obviously, whoever fills Pelosi’s shoes — or heels, to put it more accurately, even at her 80-plus years of age — will wield less influence than the woman who literally wrote the book on “The Art of Power.” Taking for near-certainty that a Democrat will win the race for Pelosi’s seat in 2026, San Francisco voters will have to decide what they want the Democratic Party to be and what role they want their representative to play in it.
And that’s a decision San Franciscans haven’t really been confronted with in decades.
