To a degree, Jay Edelson, the class-action litigator who has made himself a constant thorn in the side of Silicon Valley’s biggest companies, likes to present a laid-back image. No power suits and wing tips for him—he prefers hoodies and sneakers. His constant companion at his Chicago office is Arlo, a white-and-gray sheepadoodle. On workday breaks, he likes to challenge employees at his firm, Edelson PC, to pickleball on a nearby court.

But it doesn’t take much to rile up Edelson and get him to drop the act, which happens after I suggest that his trillion-dollar opponents might see him as nothing more than a gadfly. “Gadfly?” Edelson asked, repeating the word in a sardonic tone. “That’s just not how I see myself in the world.” He then described his attitude toward tech in crude terms: “It’s ‘Fuck those guys.’”

Lately, he’s been going after the industry’s AI ambitions, and he has been plenty busy. In the past year, he has shared in a billion-dollar settlement from Anthropic over copyright infringement and filed three headline-grabbing cases against OpenAI and Google regarding their AI chatbots that have quickly come to epitomize this moment of growing unease with the technology. Meanwhile, he is preparing to file another case against OpenAI, possibly as soon as next week, which hasn’t been previously reported. The alleged details are surreal: Edelson’s client, a woman, claims ChatGPT turned her then-boyfriend into a stalker.