Pelosi Unleashes Her Political Machine In Fight To Replace Her

SAN FRANCISCO — Nancy Pelosi is unleashing her political machine to block one of California's most prominent state lawmakers from replacing her in Congress, bringing an increasingly bitter feud to a head inside San Francisco's Democratic establishment.

The latest clash erupted after Pelosi and her allies publicly blasted Scott Wiener's campaign last week over an AI-powered chatbot imitating her preferred successor, San Francisco Supervisor Connie Chan, calling the bot “sexist” and a source of “harmful racial tropes that echo Trump birtherism.”

But if Pelosi's effort to sink Wiener, the frontrunner in the race, is now bursting into public view, it has been gaining momentum for weeks in San Francisco. Marshaling her vast political network ahead of the November election, she's hosted multiple six-figure fundraisers for Chan, lined up endorsements from Capitol Hill allies and even loaned a top adviser to her campaign.

Last month, Pelosi called civil-rights icon Dolores Huerta and urged her unsuccessfully to retract her sole endorsement of Wiener and support Chan, according to two labor organizers who were granted anonymity to discuss a private call.

It’s an all-out show of force from one of the most dominant figures ever to emerge from San Francisco politics — and a sign of how much Pelosi still has at stake in her hometown as she prepares to leave Capitol Hill. After decades spent building one of the most formidable political operations in the country, she is now deploying its money, relationships and institutional muscle, seeking not only to determine who inherits her seat but to shape the next generation of power in a city she has represented for nearly 40 years.

“You’re talking about someone who was speaker of the House and her legacy,” said Kim Tavaglione, executive director of the San Francisco Labor Council and a Pelosi ally.

Wiener, a high-profile lawmaker who has frequently spoken of Pelosi in a deferential and reverential tone, is suddenly pushing back aggressively amid polling that shows a tightening race after he finished first in the state’s top-two primary.

“Nancy has basically taken over Connie's campaign,” Wiener told POLITICO. “I'm running an independent campaign with enormous grassroots support, and no one has taken over my campaign.”

Pelosi has insisted her support for Chan is driven solely by her respect for the candidate, who shares her close ties to labor unions and would be the first member of Congress to hail from the city's large and powerful Asian American community. Pelosi has also expressed concern about a loss of female representation in the Bay Area’s congressional delegation — prominent lawmakers from the region, including Dianne Feinstein, Kamala Harris, Jackie Speier and Anna Eshoo, have all been succeeded by men.

When asked at a recent event about the possibility of Wiener succeeding her, Pelosi declined to discuss the senator by name. “I’m for Connie Chan. I’m very enthusiastic about Connie Chan,” she said as she was whisked into an elevator.

Politically, Wiener and Pelosi are both considered business-friendly moderate Democrats by San Francisco standards. But Wiener bitterly clashed with some of Pelosi’s most loyal constituencies in labor, including with teachers and the building trades, often over his proposals to fast-track housing construction and his support from real-estate developers.

And then there was his years-long shadow campaign to succeed her and the timing of his entry into the race — before Pelosi announced she would not seek reelection last fall. Pelosi had said she would wait to share her plans until after California’s November special election, when voters approved a ballot measure to redraw the state’s congressional map to favor Democrats and fight Texas’ Republican-led gerrymander. He announced his campaign in late October.

Tavaglione said Wiener's move “really got underneath her skin because it was all about fighting Donald Trump, but he wants it to be all about him.”

The timing of Wiener’s campaign launch has remained a bitter point for Pelosi’s allies nearly a year later. Former Mayor Willie Brown, a longtime friend of Pelosi, said Wiener had assured him, during a lunch at Sam’s Grill, a political hotspot in downtown San Francisco, that he wouldn’t announce until Pelosi made her decision.

“He said he had no intentions of running against Nancy — one week later he announced against Nancy,” Brown told POLITICO. “And I’ll never forget that.”

Wiener said he never made any commitments to Brown, who’s since endorsed Chan, about his campaign plans. He added, “That is fabrication, completely made up. Willie Brown is being a political operative here.”

Wiener’s supporters paint a vastly different picture of the feud, arguing the tension was driven by the Pelosi family’s political ambition. Christine Pelosi, the former speaker’s daughter and a longtime party organizer, was widely speculated to be eyeing the seat as well. The younger Pelosi ultimately opted to run for Wiener’s seat in the state Senate instead, and her mother endorsed Chan six months later.

Christine Pelosi said in a text message Sunday, “Well, if we have learned anything this week after the AI deep fake against Connie Chan, it should be not to put words in a woman’s mouth — but apparently that problem persists among people who never asked me about my personal plans and are trying to use me for their own political purposes.”

But Wiener allies speculate Pelosi had wanted her daughter to run for Congress and pivoted to Chan when a head-to-head matchup between Christine Pelosi and Wiener looked daunting.

“Pelosi is the vintage powerbroker here,” said a prominent labor organizer supporting Wiener, who was granted anonymity to speak candidly. “Let’s be real about what this is: It’s more a personal retribution. It’s about Pelosi being able to continue to broker power in San Francisco.”

Wiener said he jumped into the race before Pelosi’s retirement announcement because Saikat Chakrabarti, a wealthy former tech engineer, had mounted a tougher-than-expected primary campaign and Wiener needed time to raise money in the likelihood Pelosi wouldn’t run again.

“I deferred for years,” Wiener said. “I went out of my way to be as respectful as humanly possible because I do think so highly of her.”

But the hostility hit a fever pitch in recent days, as Pelosi and Wiener traded barbs directly over his campaign’s chatbot mocking Chan. Pelosi’s letter denouncing Wiener was co-signed by fellow California Rep. Zoe Lofgren and eight other female Democrats, as well as a host of prominent Democratic political clubs in San Francisco.

“Women have spent generations fighting to have our own voices heard in the halls of power,” the letter said. “We should not have to fight against artificial intelligence putting words in our mouths.”

The letter came after Wiener — who authored California’s landmark AI transparency law last year — stood up billboards in San Francisco, directing users to a chatbot called ConnieChan.ai. The bot appears to mock Chan’s record opposing housing and public transit projects. “I’m Connie, the world’s first AI trained to say ‘no’ to anything you ask,” the site says.

On Friday afternoon, Wiener apologized and announced he would take down the chatbot and the billboards. He said, “Our use of an AI chatbot clearly missed the mark. The conversation became about the tactic instead of the issues that actually matter to San Franciscans.”

Chan’s campaign has previously said the chatbot had racist and sexist undertones because of how it responded, or wouldn’t respond, to prompts about Chan’s accent and citizenship status. Wiener’s campaign, before his apology, said that a handful of Chan’s supporters bombarded the chatbot with dozens of prompts that sought to coax it into making offensive references.

Wiener, in a statement a day earlier, slammed Pelosi for opposing his first attempt at AI safety and transparency legislation that was ultimately vetoed in 2024 by Gov. Gavin Newsom, at Pelosi’s urging. He added, “It is particularly ironic that Speaker Emerita Pelosi is expressing concern about AI, when Speaker Emerita Pelosi played a key role, aligned with Big Tech, in killing my landmark AI safety bill.”

Chan campaign spokesperson Ian Krager, an adviser on leave from Pelosi’s office, criticized Wiener for defending his “bigotry bot” and “attacking women who condemned its racism and sexism.”

Pelosi declined to comment for this story.

The AI fracas is likely a preview of how bruising the race could become ahead of November. San Francisco politics is famously sharp-elbowed and parochial, and the city’s political establishment is sharply divided over the race.

“People are kind of puzzled by it,” said one veteran consultant who isn’t involved in the race. “(Pelosi) could just retire and ride into the sunset. But she’s got to defeat someone who, outside of (Mayor) Daniel Lurie, is one of the most popular public servants.”

On top of Pelosi, Chan has the support of Sen. Adam Schiff and a host of major progressive groups including the California Working Families Party and Our Revolution. Wiener is endorsed by both the San Francisco and California Democratic Party, as well as a majority of the city’s moderate-leaning Board of Supervisors. He is also supported by several large labor unions, including the California Conference of Carpenters and United Food and Commercial Workers union.

Wiener said he first met Pelosi almost 26 years ago, when he was a young organizer and she came to a political event at a gay bar in the Castro neighborhood. He said they became allies and she backed Wiener in his campaigns for county Democratic Party and city supervisor.

He said while the relationship has become contentious, he doesn’t consider it a personal animosity. Wiener said he “respects (Pelosi) for fighting hard for her candidate” and always anticipated a full-throated fight.

“Nancy Pelosi, she plays for keeps. She’s a fighter, and that's why we love her so much,” he added. “Obviously, I'm now on the receiving end … and that's not pleasant. She can dunk on me over and over again, and I will still think the world of her.”

Tyler Katzenberger and Chase DiFeliciantonio contributed to this report.