Generally speaking, it is not considered a good idea to represent yourself in court. But there is another, potentially worse route: you can say that you are going to represent yourself, then pass the task on to an AI avatar in order to show off the capabilities of your startup. That appears to be the approach that AI entrepreneur Jerome Dewald took, according to a report from The Register, and it was not well received by the court.
Here’s the situation that Dewald seemingly found himself in: Dewald is the plaintiff in an employment dispute with insurance firm MassMutual Metro New York and was scheduled to make an argument before the court on March 26, 2025. Dewald was diagnosed with throat cancer 25 years ago and, according to his account to The Register, still suffers from the effects of it, making continuous speaking challenging. So he asked the court if he could submit a video to make his statement—a reasonable enough request that the court seemed to have approved in advance.
What the court did not approve, based on the judge’s reaction, was the video that Dewald submitted, which was not him making a statement but instead a handsomely generic guy who the judges had never seen before. Just a couple seconds into the unnamed business stud’s statement, Associate Justice Sallie Manzanet-Daniels cut off the video and asked “Is that counsel for the case?” It was at that point Dewald revealed that the person making the statement wasn’t a person at all—it was an AI-generated video. “That is not a real person,” he told the court.
It was about then that Justice Manzanet-Daniels lost it. “It would have been nice to know that when you made your application. You did not tell me that, sir,” she said, noting that Dewald had testified at length previously and had conversations with the clerk’s office for extended periods without issue. “I don’t appreciate being misled. So either you are suffering from an ailment that prevents you from being able to articulate or you don’t,” she said.
Now would probably be a good time to mention that Dewald heads an AI startup called Pro Se Pro that helps people represent themselves in legal matters with AI tools—a fact the judge seemed to know, as she told him, “You are not going to use this courtroom as a launch for your business, sir.”
To be fair to Dewald, it does not seem that his avatar was created with his own platform, which he told The Register has been at a standstill for about a year due to lack of funding. His AI representative, named “Jim” was created with a free trial to an AI service called Tavus. While he intended to make an AI version of himself to speak before the court, he couldn’t get the trial to work so, he told The Register he just settled for “one of their stock replicas, that big, beautiful hunk of a guy.”
Still, the appearance of self-promotion as well as the unexpected appearance of an AI avatar was enough to get Dewald a scolding from the court. He went on to make his argument on his own and has since copped to the fact that he probably should have provided a heads-up that he was going to use AI to present his case. Lesson learned.