ChatGPT
After the last decade we’re all familiar with the new world of political hardball.
Cross the Kingmaker? You’ve got a problem.
Seem disloyal? You know that election you’ve got coming up? It just got a lot harder.
You say your opponent isn’t a household name? That’s about to change.
We’re bringing the full force of a national superstar, a blunt-force political operation and a massive database of contacts, influencers and loyalists against you.
Good luck.
At this point we’re not surprised to see Donald Trump do that.
But we are when it is Nancy Pelosi.
Pelosi is big mad at State Sen. Scott Wiener, who is running for her seat in Congress. One that Pelosi held for 38 years. And she’s showing her displeasure by throwing full support to Wiener’s opponent, Connie Chan.
It’s not just that Pelosi is putting her thumb on the scale. It’s the size of her thumb.
Nationally, and especially in San Francisco, Pelosi is a political megastar. She caused a “meltdown” when she stood, pointed and confronted Trump in the cabinet in 2019. She tore his State of the Union speech in half in front of him on live national television.
She’s a national treasure and I assume it is just a matter of time before San Francisco decides which freeway, government building or park it will name after her.
So what’s she doing in this local squabble?
Because she’s not just endorsing Chan. It’s no exaggeration to say this is a full-on assault on Wiener, the long-time SF political animal.
She’s posting slams against Wiener on X. She assigned her veteran communications director Ian Krager to the Chan campaign. As no less an authority than Politico put it, Pelosi has:
“Unleashed her political machine . . . marshaling her vast political network ahead of the November election, she’s hosted multiple six-figure fundraisers for Chan, (and) lined up endorsements from Capitol Hill allies.”
Why so angry?
Well, it’s a funny story. A couple of them actually.
No one is really challenging the conventional wisdom that Wiener really annoyed Pelosi when he declared his candidacy before the Former Speaker of the House announced that she was retiring. It especially wasn’t a good look because Wiener promised to wait.
Even though almost everyone assumed Pelosi was leaving, Wiener’s announcement in October, 2025, had those in the Pelosi camp griping about Wiener’s “political opportunism . . . and raw ambition.”
An ambitious politician? Alert the media.
Pelosi did take a long time to announce, finally doing so in November, but it may have been due to potential reason number two — that Pelosi wanted to roll the seat over to her daughter, Christine.
Wiener’s entry, and his deep connections in the district from serving on the Board of Supervisors (2011-2016) and State Senate (2016 to the present) made Christine’s chances evaporate. She’s running instead for Wiener’s State Senate seat.
Everybody wants their kids to get ahead, but this IS an important political position. As a very smart SF pundit put it, in bright blue San Francisco, “Somebody could be in this seat for 20 years.”
Christine Pelosi, whose political experience might be best described as “interested observer,” wouldn’t seem to have the receipts for the job.
Chan isn’t much more experienced. She’s a former legislative aide who was elected supervisor twice, beginning in 2020. Even her campaign website is long on her inspirational story as an immigrant from Hong Kong and short on political experience.
And that was pretty much how voters saw it. In the primary, Wiener got 43 percent of the vote and Chan only 30.
But the Pelosi factor has narrowed the race. Now it is more like five points.
And to the chagrin of Wiener supporters (I refuse to call them Wiener Dawgs, even though it is right there) his campaign has stepped on a few rakes.
The big one is the ChatGPT fuss, where Wiener’s brain trust released ConninChan.ai. It was a chatbot — “clearly a parody” Wiener has said — that pretended to vocalize Chan’s opinions.
The joke was that whatever you asked it, the chatbot said no. It was a play on what is actually a good issue for Wiener. Chan has voted against some Wiener-backed initiatives, including affordable house legislation, which is popular.
You can picture the thinking in Camp Wiener. Humm, AI is hot and trendy, Chan is always saying no. We’ll get a message across and look cool.
You’ll be surprised to hear that’s not how the Chan/Pelosi folks saw it. Pelosi herself took to X to call it “a gross misuse of AI” and a disturbing willingness to erase women’s agency.”
Communications director Krager accused Wiener’s campaign of “mocking an immigrant woman of color.”
That seems a stretch.
Also, Wiener said that Chan operatives were getting on the Chatbot and asking “malicious” questions about her race, her accent and ethnicity in the hope of getting a salacious answer they could use. (The chatbot only said no.)
So let’s get off our moral high horse shall we? It’s politics.
Wiener removed the chatbot and apologized. But it was a misstep, mostly because it takes away from a legitimate talking point — Chan’s thin resume.
Anyhow, we have a ways to go to the November election, but I hope we can reach a simple truth here.
Very sorry to hear that Nancy Pelosi is mad. But Scott Wiener is, by any possible measure, the best candidate.
He is, everyone admits, an absolutely relentless legislative machine. The joke in the senate in Sacramento was that they suffered from “Wiener fatigue,” because he is constantly coming up with new legislation.
His commitment to affordable house is absolutely key to his San Francisco constituents. He’s a dependable liberal democrat, an outspoken and fearless critic of Trump and someone with over a decade of political experience.
He would be an excellent representative for San Francisco and the country.
Again, we yield to no one in our admiration for the career and achievements of Nancy Pelosi.
But this looks petty.
Contact C.W. Nevius at cwnevius@gmail.com. Threads and Twitter: @cwnevius
This race means little to me, but now I'm interested thanks to your analysis. Thanks, Chuck...
Agreed. I'm disappointed in Pelosi , who I thought (foolishly, it seems) was above engaging in such blatant tRumpian political vengeance. Apparently holding power for such a long time really doe to go one's head ... and not it a good way.