Sam Singer knows a disaster when he sees one.
The disaster in question: Sen. Scott Wiener’s short-lived AI chatbot, a self-admitted “push the envelope” move designed to surface negative talking points about his congressional opponent, Supervisor Connie Chan, and her legislative record.
“This was an interesting communications experiment. It didn’t work. The right thing to do is to apologize and take it down,” said Singer, a veteran crisis communications expert known as the Master of Disaster. “That’s what I would tell them.”
Singer offered his advice to Mission Local at around 1 p.m. on Friday. Only three hours later, Wiener did just that.
The chatbot launched on Monday, Aug. 3, with a splash. Politico covered the bot in its political newsletter, and billboards went up in San Francisco’s Richmond District, Chan’s home turf — “Let’s do nothing together,” the billboards read.
City officials and Chan’s supporters were quick to criticize the chatbot, including Speaker Emerita Nancy Pelosi, who is backing Chan as her successor. Wiener’s team initially doubled down on the AI bot, arguing that it served to bring attention to policy issues, before ultimately backing down.
“Our use of an AI chatbot clearly missed the mark,” Wiener said in a statement released by his campaign. “The conversation became about the tactic instead of the issues that actually matter to San Franciscans.”
“I heard from many people who loved the idea, and I appreciate their support. But many others were offended, and I apologize for causing that offense. Innovation means trying new things, and it also means being honest when something doesn’t land the way you intended,” the statement continued.
The two billboards, which were both installed in the Richmond District, will also be taken down soon, according to Wiener’s campaign.
The chatbot also prompted the creation of a reciprocal site targeting Wiener’s record, although it is unclear who created that site.
Wiener’s chatbot may be inactive, but Chan’s team is hardly ready to let it go.
“Scott Wiener can rightly take down his bigotry bot, but he can’t erase the concerns it raised among San Franciscans about his character and judgment,” said Ian Krager, Chan’s spokesperson.
“San Franciscans deserve better than a campaign funded by Big AI weaponizing the technology to mock an immigrant woman of color, doubling down after justified outrage, then reversing course and shrugging it off as simply ‘missing the mark.’”
While Wiener lost the AI chatbot battle, some watching the race think it may also have proven useful in the congressional race war.
“You have to define your opponent,” said political consultant Nate Ballard. “With this hit, he succeeded in defining her on his terms, in a way that was attention-grabbing.”
The bot was designed as a parody to answer questions on Chan’s legislative record — or, as the site read, “say no to anything you ask.” According to Wiener’s campaign, over the course of 27 hours, the chatbot received 5,058 questions.
“He could have spent $1 million on TV spots and never gotten the attention that he did,” said Ballard. “It was an astonishingly effective negative hit, but these things can’t go on forever. There’s a pendulum that swings — you’ve got to be disciplined about when to get in and when to get out.”
While Ballard suggested the chatbot had a shelf life, others felt it was ill-advised to do this at all: Numerous government officials were quick to denounce the chatbot. California Lt. Gov. Eleni Kounalakis wrote that “AI-generated impersonation has no place in our politics,” and, notably, Pelosi issued a statement criticizing the tool.
“Women have spent generations fighting to have our own voices heard in the halls of power,” read the statement from Pelosi. “ We should not have to fight against artificial intelligence putting words into our mouths.”
Jim Ross, a veteran political consultant, said that Wiener’s chatbot backfired in that it reinforced critiques that he is in the pocket of big technology and doesn’t understand the Chinese community. “All of those things are really problematic for him.”
Singer, who praises aggression in response to aggression, said Chan’s campaign handled this well.
“I will hand it to Connie Chan’s campaign and her supporters,” said Singer. “They took something and they threw gasoline on it and they created a big fire. You have to hand them a tip of the hat on that front.”
This was not a “legitimate critique” of Connie Chan. It was a blatantly, vividly, sexist and racist attempt to belittle an honorable woman who is serving her community honestly and admirably. This AI hit, from Scott Wiener, who swallows the bounty of the wealthy AI industry while mouthing an interest in controlling them, shows that he himself is NOT honorable or admirable. It’s a slimy, desperate tactic, launched when Connie Chan is dramatically narrowing the gap between them, and it is disqualifying for Scott Wiener. Shame on him.
Wiener is a sellout for Big AI, it’s literally that simple. That he gets called on it and reacts is merely evidence of him being aware of his complicity in same.
What specifically was racist or sexist? That part wasn’t in the article. Did the chatbot mention her gender or race somewhere?
no it wasn’t. she’s awful.
Wienerites are full of his chutzpah.
Cozying up to AI and running a negative, mocking campaign is a great way to cement progressives’ and particularly women progressives’ votes for Chan, Weiner. What a creepy self-own.
As someone who’s changed my mind on this issue, I support making it easier to build more housing in SF after listening to people who were able to engage the issue respectfully and based on data, not because of stunts like this. If you lead with disrespect and mockery people will be less inclined to trust you and less inclined to believe you can actually back up your position.
Scott Wiener has not encouraged low income housing for a damn, you are mislead.
Weiner: “No more Mr. Nice Guy”. In his early days, as a bicycle riding friend of the common citizen, Weiner charmed voters with his easy manner and progressive legislation. As happens to many of our heroes, he has morphed into his evil twin, lying and slandering as he moves up the ladder of political power. Take a look at this new Scott Weiner, those of you who, like me, supported him in his journey. With the help of his billionaire high tech supporters, he has morphed into, as the graffiti aptly put it, a “white devil” who savagely attacks a highly regarded female elected official for her status as an Asian woman and immigrant, then blames it all on an AI chatbot!
When a campaign has no affordability agenda during a torrential crisis in affordability, then they can only double down on identity scolding.
Here are Tim Redmond’s observations on Weiner’s extremely statesman-like campaign techniques. Remind you of anybody on the national stage?
“Wiener’s racist, sexist Anthropic AI chatbot attacks Chan–and it’s weird and stupid and gross” https://48hills.org/2026/08/wieners-racist-sexist-anthropic-ai-chatbot-attacks-chan-and-its-weird-and-stupid/
So petty and disappointing. That chatbot stunt actually said more about Wiener than Chan. I am glad it backfired.
How about running campaigns on issues that are important to people and see which one wins instead of smearing the opponent? Show some class!
Didn’t her supporters, extolling: “ vote Connie Chan,” threaten and chase him out of the trans march?
So so sorry about her hurt fweelings.
Being escorted from the Trans March was a staged “feel sorry for me” by Scott Wiener. Mark Leno and Bevan Dufty have both been removed from the event in past years, as have other politicians. It was well known to Scott that this would likely happen, so he took the opportunity to whine to everyone and anyone that he was treated so unfairly for the trans community. Waaahhhh!
Can’t stand either candidate, but Pelosi could make better use of her time keeping the bottle and steering wheel away from her husband than campaigning for Chan.
Can somebody please explain to this puzzled Berkeley reader why using AI to generate a couple of billboards accusing Chang of being a “do-nothing” politician is “racist, bigoted, anti-woman, and anti-immigrant”?
Either a lot of the AI chatbot content has been left out of this article or Chang’s defenders are being ridiculous.
sorry for my typos of Connie Chan’s name (i’m editing on my phone, which just typed “exiting” but fortunately I noticed that).
Pelosi supports the genocide in Gaza, and Connie Chan’s supporters claim to be against it.
How do they handle that contradiction? Pelosi ran the house for years and gave AIPAC everything they wanted.
Now she’s giving AIPAC Connie Chan.
Connie Chan signed onto a cease-fire resolution in 2023, when it was a much more politically risky move. She has since consistently campaigned on ending US aid to Isr**l. Pelosi endorsed her despite this because Weiner really is THAT BAD.
In 2024, Pelosi also endorsed Dean Preston, a socialist, for D5 Supervisor against a moderate challenger backed by Weiner, and the rest of the SF establishment. Pelosi has consistently been supporting candidates to her left in recent elections. The correct read of this situation is that the SF moderate establishment has moved SO FAR to the right, that even Pelosi can’t support them.
This whole thing from the Chan campaign is, transparently, manufactured outrage. Chan staffers kept prompting the chatbot until it said something, which if you squint really hard, is somehow offensive(?). As far as I can tell, the only controversial remark was saying she had a “San Francisco accent”; quite a leap in my mind to “mock(ing) an immigrant woman of color”.
And the point the Wiener campaign is making is quite accurate: she’s got a long history blocking much-needed new housing.
So you support Billionaire backed lying chatbots because… why?
It’s astonishing how some good-faith comments/ responses simply disappear without any explanation and without a trace. Has Mission Local outsourced it’s “moderation” to NextDoor? Really people, do better!
Roger —
These comments are moderated manually and it can take a while to get to them. I understand the expectation that everything happens instantly with the push of a button but this thing doesn’t.
Yours,
JE
Can we just flip a coin and be done listening to these two power hungry graspers? It’s going to be fantastic when one of them loses and very dissapointing when one of them wins. It’s too much to ask for Lincoln Douglas but chatbots and arguments about who is meaner? There are more elevated debates at recess on any SFUSD playground than in this contest; and more meaningful outcomes.
Hilarious that the graffitist had to write “white devil” in English only.
I trust a “white devil” as contrasted to an asian devil. The devil is in the details after all.
She’s positioning herself as the Israel of candidates. You can’t criticize her without it being racist. Me? I can’t respond to the Chan campaign’s whiny complaints about legitimate critiques of her positions without swearing, so I guess I’ll just keep quiet.
“Sometimes my accent is so thick I can’t understand myself.”
We’d all love to hear you explain why that’s a legitimate critique.
“I Like Housing”: You have the right to remain silent. Use it.
Meanwhile: the revolting, Trumpian racist Wiener/chatbox snarks – that Weiner owns, no matter how much he and his minions weasel and squirm away – provide a true window into his character. And they were despicable. And absolutely disqualifying. “Misfire” indeed.
You can criticize with some sense of decorum and civility. Its also just gross to use an AI likeness of a person. Its a bit ironic you’re posting anonymously to what is clearly an invasion of privacy.
His AI Chatbot said it couldn’t understand itself as the accent was so thick.
Love this : “She’s positioning herself as the Israel of candidates. “