Congressional candidates Connie Chan and Scott Wiener debate at the Sydney Goldstein Theater in San Francisco on March 31. The winner will replace retiring Rep. Nancy Pelosi, and the district will get its first new representative since 1987.

Congressional candidates Connie Chan and Scott Wiener debate at the Sydney Goldstein Theater in San Francisco on March 31. The winner will replace retiring Rep. Nancy Pelosi, and the district will get its first new representative since 1987.

Carlos Avila Gonzalez/S.F. Chronicle

Artificial intelligence is easy. Comedy is hard. Just ask state Sen. Scott Wiener.

Wiener is locked in a tightening race with Supervisor Connie Chan to succeed San Francisco Rep. Nancy Pelosi, and the contest is shaping up to be the no-room-for-error, marquee U.S. House race in California.

So it’s something of a head-scratcher that the Wiener campaign decided to set up a website called ConnieChan.ai that featured a chatbot Chan imitator. 

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If you asked the chatbot about Chan’s positions on issues, it spat back answers that seemed designed to get a laugh. 

“I’m Connie, the world’s first AI trained to say ‘no’ to anything you ask … Bring me an idea and I’ll explain why it can’t, shouldn’t, and won’t happen.”

Like I said, comedy is hard. Take it from a political cartoonist. 

Predictably, the Chan campaign exploded, decrying the chatbot as “racist” and “sexist.” Critics included Pelosi, who has endorsed Chan and whose daughter Christine happens to be running to succeed Wiener in the state Senate.

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In an open letter posted on X (now that’s funny, using Elon Musk’s social media platform to complain about AI), Pelosi and eight other Democratic female lawmakers, including Rep. Zoe Lofgren of San Jose, blasted the use of the chatbot.

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

Another irony here is that Wiener is the author of Senate Bill 1047, AI regulation legislation that Gov. Gavin Newsom finally signed last year — after sending it back to the Senate for tightening — so his potential Big Tech 2028 presidential campaign funders weren’t singled out. 

To be sure, politics is not without its share of free cartoon ideas.

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In his initial defense, Wiener correctly pointed out that some Chan supporters with time on their hands peppered ConnieChan.ai with leading questions, and the chatbot refused to play along, indicating some modicum of intelligence.

“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, Senate Bill 1047, a bill that was broadly supported by pro-AI regulation advocates, labor unions, national security experts, biosecurity experts, and many progressive leaders,” Wiener said in his own statement.

So much for the eerie quiet that had typified the relationship between Wiener and Pelosi and left so many political observers speculating about bad blood.  

But still, why did Wiener, who has taken the lead in trying to rein in AI companies, resort to using the technology to attack Chan? Wiener spox Joe Arellano said the ChanBot was an attempt to tap into the “AI craze overtaking the city.”

How’s that for a punchline?

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One wonders what that writer’s room sounded like when someone brought up the ChanBot idea. Was there no one in attendance who deigned to push back? To point out that Wiener’s brand as a champion of AI regulation might take a hit from this silliness? And how could no one on his team have seen that this would come back to bite the senator? 

Instead, mistakes were made, accusations were thrown, the campaign quickly pulled the site and the San Francisco billboards advertising it, and Wiener apologized. 

“My campaign created ConnieChan.ai as a parody to draw attention to my opponent’s record of delay and obstruction around housing, public transit, and other critical needs,” Wiener said in a statement. 

Wiener, of course, isn’t the only one using AI in politics. President Donald Trump is famous for posting all sorts of crazy AI slop featuring him in heroic poses, mostly involving him having impressive pectoral and abdominal muscles — now that’s comedy gold. 

In the California governor race, GOP nominee Steve Hilton posted an AI animation ad featuring a likeness of his Democratic opponent, Xavier Becerra, as Nero and a would-be Gavin Newsom as, um, another Nero, mocking poor Californians who can’t afford gasoline. Hilton is portrayed as a heroic, rugged, much-taller-than-he-is gladiator fighting the dictators while sweating. His British accent is pretty faint; he almost sounds like he’s from Fresno. 

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Hilton neglects to mention his favorite dictator at 1600 Pennsylvania Ave. and the role his misguided war in Iran has had on gas prices.

Wiener’s foray into the use of AI should tell him that SB1047 might find the addition of a ban on AI technology in political ads not only good for him, but good for California voters sincerely trying to inform themselves in this increasingly atomized information environment.

We’re all petrified of AI, and we should be. Wiener’s bill was a good first step in mitigating the more pernicious effects. 

But ConnieChan.ai ain’t funny, and neither is AI slop-infused political advertising. 

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While it’s clear that there were relevant points raised on the site, there are lots of other ways to communicate Chan’s NIMBYism.

Maybe Wiener should try drawing a political cartoon. 

Jack Ohman is a Pulitzer Prize-winning editorial cartoonist and columnist who also writes at https://substack.com/@jackohman