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Lawyer for Guy Who Sued Women Used AI, Losing Case Against Meta
The lawyer who sued 27 women and one man after being called “clingy” and “psycho” in a Facebook group had his case against Meta dismissed. The judge suggested that the lawyer used AI-generated errors and non-existent citations.
In D’Ambrosio’s complaint, he claimed that Facebook profited from disparaging posts about him in a Chicago-based Are We Dating the Same Guy (AWDTSG) group. Judge David Hamilton wrote: “The brief included no citation to any legislative findings, let alone any including the statute’s targets as the brief asserted… These mistakes and fictitious quotations bear the hallmarks of the misuse of generative artificial intelligence.”
The detail was spotted by attorney Rob Freund on Twitter:
The Chicago man who brought a defamation case over FB comments in "Are We Dating the Same Guy?" group appealed the dismissal of his case.
He loses again, and this time the court calls out his lawyers’ AI misuse, noting some irony around it.
The appellate brief included several…
D’Ambrosio claimed that a woman in the group said she had blocked his number. She wrote: “Very clingy [and] very fast,” she said. “Flaunted money very awkwardly and kept talking about how I don’t want to see his bad side.” She blocked his number, and he texted her from another phone. His response was: “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***.”
In 2024, D’Ambrosio was sentenced to a year in prison for tax fraud. His attorney at the time suggested that his client relied on a cousin for his taxes, making him innocent. D’Ambrosio didn’t argue his “reportedly obnoxious behavior on dates and after a breakup” as listed in the AWDTSG group until it came time for oral arguments to appeal a dismissal of the case.
Judge Hamilton lists several reasons why D’Ambrosio doesn’t have a strong enough case based on Meta violating any right-to-publicity laws or profiting off his likeness through the AWDTSG group. Among them: his attorney Aaron Walner’s “sloppy” use of AI.
“We see such sloppy work in briefs fairly often, and almost always let it pass without comment as we try to focus on the merits of appeals,” Hamilton wrote. “But the next sentence in attorney Walner’s opening brief for D’Ambrosio said. Not only did Walner cite cases that didn’t support his argument, but the only place judges could find one of the citations was in a decision that supported the opposite of the point he was apparently trying to make.”
Aaron Walner is an attorney at Marc Trent’s law firm. The judge points out that Trent’s website brags extensively about his use of AI, listing “AI-Powered Case Management” and “Smarter Legal Strategies” as ways he practices law using LLMs such as the ones like ChatGPT. The site claims that these tools automate document review, flagging key information and identifying relevant case law in seconds.
The court demanded Walner, Trent, and D’Ambrosio answer for their AI-generated filings or face sanctions. Lawyers getting caught and sanctioned for using AI and wasting the court’s time and clients’ resources happens so often now it barely makes the news anymore. This phenomenon started in the last year, and has since exploded into a legal-world epidemic, with judges’ patience wearing thin and more people choosing to represent themselves in court. Lawyers, meanwhile, blame everything from family emergencies to technical difficulties when they get caught, and often throw their own paralegals under the bus.
Trent Law Firm did not respond to a request for comment.
“We don’t just use AI for the sake of it. Every tool and strategy is aimed at one thing: winning your case,” Trent’s site says. In D’Ambrosio’s case, it helped lose it.
Key Takeaways
- Lawyers are increasingly using AI in their work, sometimes leading to serious consequences for them and their clients.
- The misuse of AI can lead to the dismissal of cases or result in sanctions from judges.
- Judges are becoming more aware of AI-generated errors and are taking stricter action against those found guilty of such misconduct.
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