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 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 chabot, 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,” said Wiener, 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.
A billboard paid by Scott Wiener’s campaign on Geary Boulevard and 25th Avenue. Photo by Nicholas David.
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.”
