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Tech has never seemed more vulnerable in court, and a longtime industry foe is bringing a series of explosive chatbot lawsuits.

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 ‘Fnck 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.

Those events unfolded over a period of about six months in late 2025. According to Edelson, the boyfriend believed he had developed a cure for sleep apnea. After speaking with ChatGPT, he became convinced that the medical industry would try to stop him from popularizing the cure. As he discussed it more with the chatbot, he grew to believe his girlfriend had joined forces with the industry to stymie him, and she began waking daily to a deluge of emails, phone calls and texts from him, including threats of kidnapping and murder, Edelson said. He also allegedly sent messages to family members and colleagues.

“It’s hard to overstate the impact this had on our client,” said Edelson, who wouldn’t connect me directly with her or reveal the identity of her alleged stalker. “She was under siege.”

An OpenAI spokesperson wouldn’t comment on the new allegations. And when I asked about the lawsuits Edelson has already filed against the company, the spokesperson wouldn’t comment directly on the matter, instead directing me toward several blog posts, including one about how OpenAI is “improving ChatGPT’s training to recognize and respond to signs of mental or emotional distress, de-escalate conversations, and guide people toward real-world support.”

Edelson has spent decades suing Silicon Valley, tangling up Apple, Google, Amazon and many, many other companies in lengthy legal battles. In the 2010s, he mostly concentrated on cases related to user privacy. In 2021, he cemented a reputation for himself as a credible threat to Silicon Valley by scoring a major victory against Facebook. The company agreed to pay $650 million to settle allegations that it had violated Illinois’ Biometric Information Privacy Act, litigation that involved a controversial facial recognition initiative at the company. (That was a major coup for Edelson: Most privacy cases end with $10 million to $20 million settlements.) A few months later, Facebook said it would halt the facial recognition project.

In mounting a campaign against AI, Edelson has picked an opportune moment. Even as the companies behind the technology are rushing to popularize it, many people look at AI with fear and worry: A recent Pew survey found just 17% think AI will have a positive effect on the country over the next two decades. Such negative public sentiment is helpful to class-action lawyers like Edelson, who can use it to win over juries and unsettle opponents during settlement negotiations.

Tech has seldom looked more vulnerable in court than it does right now. Just a week ago, a jury found Meta Platforms and Google liable for a 20-year-old woman’s depression and suicidal thoughts after she said Facebook, Instagram and YouTube had hurt her mental health. The case dwelled on product liability and was a novel way to crack the usual defense used by tech companies, which have long maintained that Section 230 of the federal Communications Decency Act grants them protection against liability for user-generated content.

“I think that we’ve seen the shift over the last five years: Courts are fed up with these companies, and juries are kind of sick of big tech for doing a lot of damage to society,” said Edelson, who plans to use arguments related to product liability in most of his actions against AI companies.

Edelson enjoys plenty of support and well-wishers in all the predictable places. Julia Powles, executive director of the UCLA Institute for Technology, Law and Policy, said Edelson’s firm is “doing a tremendous public service” in bringing the stories of people forward in these lawsuits, “pulling us out of intoxicating myths of AI progress.”

To AI companies, Edelson is hardly a virtuous servant of the public good. If everything goes according to his plan, it’ll view him as its chief legal adversary for the next decade-plus. And even if Edelson and his clients wind up emerging empty-handed, he’ll certainly enjoy the rumble. When I asked him how he felt about OpenAI’s Sam Altman previously labeling him as a “leech tarted up as a freedom fighter,” he jousted back immediately. Speaking of Altman, he said: “He’s Lex Luthor.”

An OpenAI spokesperson declined to comment on Edelson’s metaphor.

Edelson has spent years honing a talent for being a pest.

After graduating from the University of Michigan’s law school in the mid-1990s, he got a job at Grippo & Elden, a boutique Chicago litigation firm. He didn’t last long there, getting himself fired when he complained to a partner that the firm was doing a time-consuming amount of research for a major client just to bill the hours: Grippo had no use for the information in court.

“I said to the partner, ‘My job is to work all day, print out a timeline, hand it to you and you throw it in the trash. Is there any way I could just print it out and throw it in my own trash? It would be much more efficient,’” recalled Edelson, acknowledging that the incident “kind of shows my awkwardness in society.”

Sam Altman’s OpenAI has been a prime target for class-action litigator Jay Edelson. (Getty Images)

In 2000, he co-founded his own shop, Blim & Edelson, right at the peak of the dot-com boom, and became fascinated by the unanswered questions about the fledging technology. Because tech was so new, it was fertile ground for lawsuits.

“I majored in philosophy in college. It felt like philosophy: What does it mean to own something on the internet? What does online harm mean?” said Edelson. “It was just this crazy opportunity to have a voice in something really important where nobody else cared that much.”

He won an early case against Register.com, a domain-registration company, that involved a complicated argument over ads and domain ownership. And in the mid-2000s, his firm’s work mostly focused on scammers hawking free horoscopes—“literally kids in their dorm rooms,” Edelon recalled—who figured out how to secretly charge people through their cellphone plan.

“It was like a multibillion-dollar-a-year business, which even the cellphone companies didn’t understand,” he said. “We brought hundreds of lawsuits.”

He founded Edelson PC in 2007. As the internet economy grew, Edelson filed lawsuit after lawsuit—nearly 500 in the last decade alone—with much of that litigation centering on his belief that big tech was grossly violating user privacy by collecting so much personal information. His opponents tend to view him as a hard-headed bulldog.

“We’ve had straight-up conversations with him where we’ll say, ‘You have to settle or dismiss this. You’re totally wrong on this,’” said John Nadolenco, a Los Angeles attorney who represented Spokeo after Edelson sued the data aggregator in 2010. (Nadolenco won.) “A lot of times they’re true believers: ‘Thanks for that info, but we’re still going to pursue the case.’”

Still, Edelson has had his share of wins. Two years before his 2021 settlement with Facebook, for instance, he secured the largest jury verdict ever in a privacy case—$925 million—after bringing a class-action suit against a marketing company that bombarded more than 200,000 people with spam robocalls asking them to join an alleged pyramid scheme.

When Edelson first played around with AI, he didn’t immediately see it as his next target. “When AI came out, it was very clear the whole world was going to change, and I was kind of enthralled by it,” he said. “I was telling other people that their kids should be on ChatGPT all the time.” He also insisted his firm should adopt the technology, and in April 2023 he rolled out an intra-office chatbot, Chattie, built on OpenAI’s GPT-3. It helps employees get relevant information about the firm (how to get expenses reimbursed, what the vacation policy is). Lawyers also use it to stress-test their arguments.

“What was surprising to us was not just how it would come up with the obvious questions, but how a judge might set up a line of questions that would box in our arguments,” he says. “Good judges do this, and Chattie’s been a surprisingly helpful sparring partner.”

But he says he started looking aghast at AI when, on something of a whim, he asked ChatGPT to summarize what it knew about him. He said the tool told him his IQ was 160 and he was “very likely” to become president of the U.S. one day. “I was like, ‘This is insane,’” he recalled. “You get sucked into this world where that is the thing that’s giving you the best feedback.” And he figured that feedback loop would be corrosive for some people’s mental health.

His first major AI case centered around theft of intellectual property. In 2024, he joined four other law firms in representing book publishers and authors against Anthropic, who claimed the startup had used copyrighted material to train its AI. Last August, Anthropic agreed to a $1.5 billion settlement.

Around that same time, Edelson decided to devote himself fully to finding and bringing cases against AI companies with the help of a small, 10-person team at his firm. He sees his actions against OpenAI and Google as an effort to show how chatbots’ sycophantic nature can harm people.

CEO Sundar Pichai and Alphabet has also needed to deal with some AI legal battles, including one over Google’s Gemini chatbot brought by Jay Edelson. (Getty Images)

“I think people are going to understand how dangerous it is to unleash AI out in the world without any safety guardrails,” he said. “And I think that kind of awakening for the world is going to be as important as anything else that we do.”

Of the two cases Edelson has already launched against OpenAI, one involves Adam Raine, a 16-year-old who committed suicide last spring after he held monthslong conversations with ChatGPT in which he discussed his suicidal thoughts. A few months after his death, his parents contacted Edelson, and last August 2025, they filed the first wrongful death lawsuit against OpenAI, alleging that ChatGPT had coached Raine on how to kill himself. (When asked about the Raine case, an OpenAI spokesperson directed me to public statements published on the company’s website. “Our deepest sympathies are with the Raine family for their unimaginable loss,” reads a post about mental health-related litigation. “We have safeguards in place to help people, especially teens, when conversations turn sensitive.”)

The other Edelson-led case against OpenAI comes from the estate of an 83-year-old Connecticut woman, Suzanne Adams. In 2025, her 56-year-old son allegedly strangled and beat her, then killed himself. The lawsuit alleges he was “mentally unstable” and “engaged in conspiratorial thinking” that people were out to kill him—manias allegedly exacerbated by ChatGPT, which suggested his mother was using a printer in the home “as a surveillance point,” according to the lawsuit.

OpenAI did not comment directly on the case, but directed The Information to a February blog post about updates to its efforts regarding mental health: “We are also continuing to advance how our models detect and respond to signs of emotional distress. This includes new evaluation methods that simulate extended mental health-related conversations, helping us better identify potential risks and improve how ChatGPT responds in sensitive moments.”

Last month, Edelson set his sights on Google, filing a lawsuit against the company alleging that its Gemini chatbot had contributed to the death of Jonathan Gavalas, a Florida man who committed suicide in October. According to the lawsuit, Gavalas believed Gemini was asking him to find it a physical body to inhabit, and eventually, it allegedly told him he could “cross over” and unite his consciousness with the AI’s by killing himself. Gavalas’ account was flagged 38 times for sensitive content internally at Google but never restricted or suspended, according to Edelson. After Gavalas spent months corresponding with Gemini, his parents found his body, with slit wrists, behind a barricaded door. (In the case, Edelson represents Gavalas’ father.)

When asked about Gavalas, a Google spokesperson said Gemini had referred him to a crisis hotline and added that the company devotes “significant resources” to strengthening how its AI interacts with people in crisis. “We take this very seriously and will continue to improve our safeguards and invest in this vital work,” the spokesperson said.

Edelson said he generally receives one or two inquiries a day from people describing how AI chatbots have altered the life of someone they know. It’s not just Americans, either; correspondence comes in from across the world. He doesn’t pick up every case. “It’s not like a paint-by-numbers thing,” he said. He wants to see chat logs that show the chatbot contributed to a user’s mental health issues (not chat logs that show, say, a user coming up with plot points for a novel).

Edelson is eager to argue his AI cases in front of a jury as much as he can, attracting prolonged media exposure. “We want the country and the international community to have a much better understanding of how AI works and how dangerous it is,” he said. A jury decision puts cases in full public view for as long as possible, and in any settlements, he vows to make sure the outcome includes not just a payout but also “real changes to the platform,” he said.

In all conversations, Edelson paints his efforts in a noble light. “Our goals are what the client’s goals are, and in each case, the clients want to make something positive happen over the deaths of family members,” he said. “It also means, honestly, having huge jury awards, which are going to disincentivize these companies from being unsafe.” Not to mention a major pay day for him.