California state Sen. Scott Wiener's campaign built a parody AI chatbot to ridicule San Francisco Supervisor Connie Chan, the candidate Nancy Pelosi endorsed to take her congressional seat, and the response from Chan's camp tells you everything about where this race stands.
The website, ConnieChan.ai, bills itself as "the world's first AI trained to say no to anything you ask." Wiener's team designed it to mock what they call Chan's record of blocking progress in San Francisco, a city where the AI industry is booming and where voters are watching two Democrats fight over who gets to inherit one of the most powerful seats in the House.
The chatbot went live this week, and the two campaigns immediately traded accusations that lay bare the fault lines of the race: Wiener's side says Chan is an obstructionist who has stood in the way of housing and development. Chan's side says Wiener is a tool of corporate AI money who put sexist, racist words in a woman's mouth. Both sides claim the moral high ground. Neither side looks particularly interested in the voters stuck living with San Francisco's failures.
Joe Arellano, Wiener's campaign spokesman, told the New York Post the chatbot was meant to "lean into the AI craze overtaking the city" while reaching voters with something that stands out. He did not apologize for the stunt.
"No lies were told in the making of this AI chatbot. This is 100% Connie Chan's record of blocking all progress in San Francisco, packaged in an easy to use tool for voters."
Arellano went further, pitching the chatbot as a creative way to let voters experience Chan's alleged pattern of saying no:
"We created ConnieChan.ai to lean into the AI craze overtaking the city and creatively reach voters with a product that stands out, highlights Connie's long record of obstruction, and lets us all do nothing... together."
Critics have described Chan as a progressive who has opposed numerous housing proposals during her time on the Board of Supervisors. Wiener's campaign clearly wants that label to define her before she can define herself on a congressional stage. The chatbot is a gimmick, but the underlying argument, that Chan blocks development in a city desperate for housing, is one Wiener intends to press hard.
Ian Krager, Chan's campaign spokesperson, did not treat the chatbot as a joke. Krager, who is on hiatus from Pelosi's own office to help Chan's campaign, unloaded on Wiener in a series of statements.
"If there was ever any doubt that Scott Wiener is bought and paid for by Big AI, he's not even trying to hide it anymore."
Krager also accused Wiener of crossing a line by using AI to put words in a female candidate's mouth:
"It's never a good idea for a man to put words in a woman's mouth, especially when they are falsities fraught with racist and sexist undertones."
The racism and sexism charges are notable because Chan was born in Hong Kong, and Krager's statement frames the chatbot as targeting her identity, not just her record. The source does not detail what specific chatbot outputs Chan's team considers racist or sexist, so voters are left to judge the claim on their own.
Krager also tried to pivot to substance, saying Chan would focus on "lowering costs for working families, standing up to powerful special interests, and delivering results for San Francisco." He dismissed the chatbot as "the tired and trite slop Scott Wiener is offering."
Nancy Pelosi endorsed Connie Chan to succeed her in Congress. That endorsement carries weight, Pelosi held the seat for decades and remains one of the most influential figures in the Democratic Party, even as questions about her own record have followed her into retirement.
But endorsements do not pay for television ads. Federal election filings from the end of June show Wiener's campaign sitting on more than $1.2 million in cash. Chan's campaign had just over $362,000, roughly a third of Wiener's war chest.
The cash gap widened this summer after Wiener was chased out of a trans march during Pride month in San Francisco. His campaign reported raking in donations after the incident, though the source does not specify exact figures tied to that event.
On top of his campaign cash, Wiener has outside help. Public First Action, a super PAC backed by AI company Anthropic, entered the race earlier this year and committed $500,000 to supporting him, Politico reported. That is real money in a House primary, and it feeds directly into Chan's argument that Wiener is beholden to corporate AI interests.
Wiener's camp counters that he authored what they describe as landmark AI safety laws that serve as a model for the rest of the country. Arellano drew a direct contrast with Chan:
"Scott wrote the landmark AI safety laws serving as the model for the rest of the country. He's been thinking about workers and safety and delivering on these issues for years. He won't be learning on the job like Supervisor Chan."
The specific laws Arellano referenced are not named or identified by bill number in the available reporting, so the scope and impact of that legislative record remains an open question for voters to examine.
This race is a contest between two Democrats in one of the most reliably left-wing districts in America. There is no Republican in the picture. The battle lines run between a state senator aligned with tech money and AI industry interests, and a city supervisor backed by the outgoing speaker emerita and her political operation.
For conservative observers, the spectacle is instructive. Pelosi spent decades accumulating power in Washington, and her financial dealings and political maneuvering have drawn scrutiny for years. Now her chosen successor is getting outspent and outmaneuvered by a rival willing to use a novelty AI website to define her before the campaign even heats up.
Chan's team wants voters to see a well-funded man backed by corporate money using technology to mock a woman of color. Wiener's team wants voters to see a supervisor who says no to everything in a city that cannot afford more obstruction. Both framings are self-serving. Neither candidate is offering San Francisco voters anything resembling accountability for the city's well-documented failures on housing, public safety, and homelessness.
The internal fractures within the Democratic Party keep surfacing in races like this one, not as ideological debates between left and center, but as turf wars over who gets to manage decline.
Meanwhile, the people of San Francisco, the ones paying the taxes, dodging the needles, and watching their neighborhoods deteriorate, get to choose between two progressives arguing over an AI chatbot while their city falls apart around them.
When the fight over who inherits Pelosi's seat comes down to a novelty website and accusations of bigotry, the real losers are not on either campaign's payroll, they are the voters left holding the bag.
