Creep Who Sued Women Who Warned Others Not To Date Him Loses Case Due To AI-Reliant Lawyer
Finally, a good use for AI!
On Tuesday, we discussed some of the kinds of sucky things about artificial intelligence — like how tech billionaires are very jazzed about a future in which AI takes over all of the jobs and there is no longer any point to anyone doing anything, (and deeply wounded that no one else is excited about that).
Well, it looks like AI has finally done something right! Sort of. In that it’s part of the reason that Chicago’s Seventh Circuit Court of Appeals has dismissed the case of Nikko D’Ambrosio, the incredible douchebag who sued 27 women for talking about what a creep he is in the Chicago “Are We Dating The Same Guy? (AWDTSG)” Facebook page, along with Facebook/Meta for supposedly “profiting” off of it and also the parents of the woman who made the initial complaint, for letting her use their home internet. Also Patreon and GoFundMe, for reasons.
One of the reasons for dismissal cited by Judge David Hamilton was that the brief submitted by the plaintiffs included “facts” and “citations” that were very obviously hallucinated by some kind of generative AI.
In this appeal, we affirm dismissal of a litany of claims arising from a few social media posts about the plaintiff’s reportedly obnoxious behavior on dates and after a breakup. We also order plaintiff and his attorneys to show cause why they should not face sanctions for frivolously appealing the dismissal of his claims against the author of some of those posts (a woman he briefly dated) and her parents. Plaintiff failed to offer even colorable grounds for reversing the claims against those defendants. Moreover, his attorney submitted a brief with fictitious quotations, citations, and claims that should have been avoided with routine citechecking. […]
The brief included no citation to any legislative findings, let alone any including the statute’s targets as the brief asserted. We could not find any reference to the phrases “amplified exposure and endangerment” or “cyber vigilantism” within the Doxing Act. There also are no legislative findings included in the codification of the Doxing Act, the session law, or any publicly available version of the bill. These mistakes and fictitious quotations bear the hallmarks of the misuse of generative artificial intelligence.
Whoops!
The detail about AI was initially discovered by lawyer Rob Freund, who posted about it on Xitter, and further reported on by 404 Media.
As it turns out, D’Ambrosio’s lawyer Marc Trent actually brags about his firm’s use of AI on their website — the address of which is literally www.marctrent.ai — in a blog post titled “How Marc Trent Uses AI to Deliver Cutting-Edge Legal Solutions.”
It reads, in part:
Here’s why it’s a game-changer:
Efficiency on Steroids: AI automates time-consuming tasks like document review and legal research, freeing up our team to focus on what really matters—your case strategy and client service.
Data-Driven Decisions: With AI, we can analyze vast amounts of data to spot patterns, predict outcomes, and craft smarter legal strategies. It’s like having a crystal ball for your case.
Personalized Client Care: AI helps us tailor our communication and services to your specific needs, ensuring you feel supported and informed every step of the way.
At MarcTrent.ai, we’re not just using AI—we’re mastering it to deliver results that traditional firms can’t match.
Probably because traditional firms do not present briefs with hallucinated AI quotations in them. It’s hard to “match” something like that when you are confined to reality.
D’Ambrosio initially filed his lawsuit in 2024, claiming that a woman who dated him had “defamed him” by posting about him in AWDTSG.
Specifically, she accused him of being “very clingy” and “very fast,” claiming that he “flaunted money very awkwardly and kept talking about how I don’t want to see his bad side, especially when he was on business calls,” and when she told him she didn’t want to spend the night with him, just the day, he sent her a series of shitty messages until she blocked his number, at which point he used another number to send her the following, very charming, message:
“Speak for yourself you ugly vial [sic] fake whore. Your ego matches that fake f****** face where you can’t even smile in pictures because your teeth are so f*****. The truth hurts b**** and my message will stay with you forever c***.”
It’s worth noting that, while neither D’Ambrosio nor his attorneys ever previously denied that he sent the message, they did try it this time. Except they couldn’t give the judge any evidence of that or further explain, because of “attorney-client privilege.”
Right around the same time he filed the initial lawsuit, this incredible catch went to federal prison for lying about his business expenses and charitable contributions on his taxes, despite the fact that his lawyer passionately argued that he was just literally too stupid to do his own taxes.
“I don’t mean this to disparage Nikko in any way, but as you can see from his educational records, he is not the most sophisticated human being. Somebody with his skill set is not doing his own taxes, and nor should he be, frankly. You go to a professional. And the professional he relied upon was his cousin,” D’Ambrosio’s other bad attorney, Christopher Grohman, explained to the court.
D’Ambrosio had claimed, falsely, that over two years, he had driven more than 474,000 miles on business-related travel and spent $263,000 in business-related meal expenses as part of his job as a salesperson for an electronic sweepstakes kiosk company that was literally run by the Chicago Outfit. He also claimed to have given $63,000 to a Chicago Catholic church that had no record of him even being a parishioner, nevermind giving them $63,000.
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The case eventually went to court in 2025 and was dismissed pretty quickly, because Section 230 exists, which means you can’t sue an online platform for what other people write about you on it, and because people are allowed to talk about how you are, in their opinion, a bad date. Naturally, he appealed and here we are, with him losing again.
There are some life lessons to be learned here, the first of which is if you are very, very concerned about people knowing that you are a douchebag who says horrible things to women, you probably should not sue 27 women for calling you a douchebag who says horrible things to women. Another would be “Hire lawyers who will tell you that this is a terrible idea that will result in the entire world knowing that you are a douchebag, and who do not have to rely on ChatGPT to file a brief.”
But perhaps the most important one is that, if you happen to be a single woman in the Chicago area (or anywhere else for that matter), you really, really, really do not want to go on a date with Nikko D’Ambrosio.
PREVIOUSLY ON WONKETTE!
OT
𝐁𝐚𝐫𝐧𝐞𝐲 𝐅𝐫𝐚𝐧𝐤, 𝐚 𝐥𝐢𝐛𝐞𝐫𝐚𝐥 𝐜𝐨𝐧𝐠𝐫𝐞𝐬𝐬𝐦𝐚𝐧 𝐚𝐧𝐝 𝐭𝐫𝐚𝐢𝐥𝐛𝐥𝐚𝐳𝐞𝐫 𝐟𝐨𝐫 𝐠𝐚𝐲 𝐫𝐢𝐠𝐡𝐭𝐬, 𝐝𝐢𝐞𝐬. 𝐇𝐞 𝐰𝐚𝐬 𝟖𝟔
Barney Frank, the longtime Democratic congressman and leading liberal who brought new visibility to gay rights and crafted the most significant reforms to the financial system in a generation, has died. He was 86.
Frank died late Tuesday, according to Jim Segel, Frank’s former campaign manager and close friend.
After representing broad swaths of Boston’s suburbs in Congress for 32 years, Frank and his husband moved to Ogunquit, Maine. He entered hospice there in April with congestive heart failure and is survived by his husband, Jim Ready, and sisters, the longtime Democratic strategist Ann Lewis and Doris Breay, along with brother David Frank.
A self-described “left-handed gay Jew,” Frank was known for his acerbic wit, combative style and focus on marginalized communities. He represented the party’s left wing while keeping close with Democratic leaders who sometimes frustrated progressives.
He is best known as a pioneer for LGBT rights. After decades of grappling with his sexuality, he publicly came out as gay in 1987, the first member of Congress to do so voluntarily. With his 2012 marriage to Ready, he became the first incumbent lawmaker on Capitol Hill to marry someone of the same sex.
https://apnews.com/article/barney-frank-congressman-democrat-gay-rights-massachusetts-2bcabf60456bc189fef2cadd393a8b76
"AI-Reliant Lawyer"
[Laughs in binary]