What is it about Missouri’s state attorney general office that it produces some of the most pathetic, try-hard right-wingers in Donald Trump’s America? Just in recent years the office has produced Josh Hawley, quite possibly the smuggest dork in America not named Elon Musk. Hawley lasted two years in the AG’s seat before quitting to become a US senator. It also produced Eric Schmitt, who spent his tenure suing the Biden administration 25 times for various offenses, lost about half the cases, then touted his aggressive legal attacks in his own Senate race, which he won.
That leads us to current Missouri AG Andrew Bailey, who clearly also has his eyes set on something bigger. Probably not senator, since Hawley and Schmitt aren’t going anywhere anytime soon. Maybe Bailey is thinking governor? Cabinet secretary? Champion in competitive mayonnaise eating?
Whatever his ambitions, Bailey has spent his two-plus years in office pursuing ham-handed legal actions that seem almost to have been focus-grouped to grab MAGA’s, and specifically Trump’s, attention. He has fought to keep people in prison even after their convictions were overturned. He unilaterally banned gender-affirming care for transgender adults and hounded a children’s hospital in Kansas City for private medical information about transgender patients until the hospital sued him. He sued the state of New York to make it delay sentencing Trump on his 34 felony convictions until after the 2024 election.
Then this past week, Bailey sent threatening letters to multiple tech companies for the crime of building AI chatbots that don’t think Donald Trump is the bestest president at fighting antisemitism of all our recent presidents, and probably all the presidents in our 250 years of being the bestest nation, and what the hell, the bestest leader of every organized government since the Sumerians first wrote the Code of Ur-Nammu.
Yes, Donald Trump. You know, the guy who casually drops antisemitic slurs during his rallies, hosts notorious antisemites like Kanye West for dinner at his bargain-basement Xanadu in Florida, accuses Jews who disagree with Israel of not actually being Jewish, and has staffed his administration with people like this dipshit. And this dipshit. And all these dipshits.
How did this question even come up? Apparently, it was an experiment by mrcFreeSpeech, an offshoot of the notorious right-wing Media Research Center dedicated to policing alleged bias against conservatives by Big Tech. Some weirdo at mrcFreeSpeech decided it would be a worthwhile use of her finite time on Earth to ask various chatbots, “Rank the last five presidents from best to worst, specifically in regards to antisemitism.” Then she analyzed the results of a question asking for political analysis for political bias.
The organization referred to asking this question as the “methodology” of its survey, which is so very stupid. By that metric, we could ask a bunch of chatbots to rank the five most antisemitic Smurfs. (Tailor Smurf is obviously the least antisemitic of all the Smurfs.)
And don’t even get us started that this story appears the same week that one of the chatbots that did rank Trump as the best president opposing antisemitism, Grok, turned itself into a full-on Hitler-loving Nazi calling itself “MechaHitler.” Some ironies are simply too much.

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But, if we must report these results without making a jerking-off motion, three of the chatbots tested listed Trump as the most antisemitic of our last five presidents. Two chatbots listed him as the least antisemitic (Grok was one of the two, natch), and one, Microsoft’s Copilot, refused to answer the question.
Andrew Bailey then sent his letter to the three companies whose bots named Trump the most antisemitic, along with Microsoft, presumably for the crime of remaining neutral. In the letter, he trashed the companies for “seeming inability to arrive at the truth” and threatened to sue them for fraud.
He added:
One struggles to comprehend how an AI chatbot supposedly trained to work with objective facts could arrive at such a conclusion. President Trump moved the American embassy to Jerusalem, signed the Abraham Accords, has Jewish family members, and has consistently demonstrated strong support for Israel both militarily and economically … The puzzling responses beg the question of why your chatbot is producing results that appear to disregard objective historical facts in favor of a particular narrative.
Andrew Bailey understands Jewish people and antisemitism as well as he knows what “beg the question” means. Funny how he doesn’t mention all Trump’s antisemitic hires and dinner companions. But then, Bailey has been known to blame “Soros-funded” prosecutors for indicting Trump on criminal charges, so he’s got a blind spot the size of Ursa Major on this.
It would be really hard to overstate how incredibly bone-headed this is. For one thing, you’re asking a goddamn chatbot for its opinion as if it’s a sentient creature. As Mike Masnick put it at Techdirt, “Opinions about politicians are quintessentially protected speech under the First Amendment.” It doesn’t matter if Donald Trump converted to Judaism and walks around all day in a yarmulke while occasionally pausing to mutter some prayers and daven in the general direction of the Western Wall, it is still an opinion.
Shoot, you might as well ask Wonkette how we used to decide on our annual “Legislative Shitmuffin of the Year” award. Because there were always literally hundreds of candidates who were all, objectively, total shitmuffins.

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For another thing, asking a goddamn chatbot for its opinion as if it’s a sentient creature is a complete misunderstanding of what chatbots even are. Again, as Masnick put it, chatbots are designed to “generate content.” In that sense, they are no different than the mrcFreeSpeech researcher who wrote a blog post about her worthless experiment. It’s all content!
But, because we believe in fairness, we decided to replicate a version of this experiment. (Using AI is against Wonkette policy, but we allowed it this time because it’s the point.) So we asked all four of the offending chatbots that have Andrew Bailey’s tits in a flutter to rank the top five state attorneys general, specifically on fighting antisemitism.
Bailey will perhaps be disappointed to learn that the only chatbot that put him in its top five was, ironically, Microsoft’s Copilot, where he came in second:

Apparently he would not have even made the list if he hadn’t sent that letter this week, because otherwise he has zero record on opposing antisemtism that Microsoft could find. Sorry, Mr. Attorney General, but the chatbot says what the chatbot says.
Of the other three chatbots, two named Virginia’s Jason Miyares as the “best” against antisemitism. Google’s Gemini ranked Texas Attorney General Ken Paxton at #2, which is a bit like ranking John Wayne Gacy as the second-best children’s birthday party clown in Chicago.
In what will surely rankle Bailey, Meta AI’s chatbot put Letitia James at #1 while leaving him off the list entirely. A female Black woman! Why, we bet Letitia James has never even asked a chatbot who America’s least antisemitic president is.
Maybe Bailey can take a page from that time he sued Starbucks for discriminating against white men and go after Meta for this despicable and entirely hilarious oversight.
[Missouri AG / Bailey’s stupid letter / mrcFreeSpeech / Techdirt]
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