OpenAI has lost a court battle to protect user privacy in its high-stakes copyright lawsuit against The New York Times. On July 2, a U.S. District Judge in New York rejected OpenAI’s appeal, cementing an order that forces the company to indefinitely retain all ChatGPT conversations—including those users have deleted, reports Ars Technica.
The decision clears the way for The Times’ legal team to search the retained logs for evidence to support its claims of widespread copyright infringement. This unprecedented ruling has sparked significant user backlash and a fierce debate over data privacy, setting a potentially alarming precedent for the entire AI industry.
The ruling stems from a June 5 order by Magistrate Judge Ona Wang, which was requested by The Times to preserve potential evidence. The newspaper argued that users might delete chats showing they used the AI to bypass its paywalls.
A ‘Bonkers’ Order: Privacy Concerns Mount Over ChatGPT Log Retention
The court’s decision has been met with alarm from privacy advocates and legal experts. They warn that forcing a company to retain data that users explicitly deleted is a dangerous overreach. The move could have a chilling effect on how people interact with AI tools, fearing their private queries could be exposed in legal proceedings.
Consumer privacy lawyer Jay Edelson described the order as “bonkers.” He expressed deep concern over the security of such sensitive information, stating, “the idea that you’ve got a bunch of lawyers who are going to be doing whatever they are with some of the most sensitive data on the planet… should make everyone uneasy.”
Edelson also noted the sheer scale of the data involved, remarking, “We are talking about billions of chats that are now going to be preserved when they weren’t going to be preserved before.”, highlighting the vast privacy implications for millions of users.
OpenAI has strongly opposed the order. The company’s COO, Brad Lightcap, called it an “overreach by the New York Times.” In a statement, he added, “We’re continuing to appeal this order so we can keep putting your trust and privacy first,” signaling the company’s intent to continue its legal fight to protect user trust and privacy.
The Copyright Battleground: A Timeline of Accusations and Defenses
This latest development is a critical moment in a legal saga that began in December 2023. The New York Times filed a landmark lawsuit against OpenAI and its key partner, Microsoft, alleging they unlawfully used millions of copyrighted articles to train their generative AI models.
The publisher is seeking billions in damages and demands the destruction of any AI models trained on its content. The financial stakes are immense, with The Times reportedly spending $7.6 million on legal fees by November 2024 alone.
The case has been fraught with complications. In November 2024, OpenAI engineers inadvertently deleted key evidence from a virtual machine, temporarily derailing the plaintiffs’ investigation. This misstep was followed by a judicial panel’s decision in April 2025 to consolidate several publisher lawsuits against the AI firms in Manhattan.
In their defense, OpenAI and Microsoft have consistently argued that their training methods are protected under the “fair use” doctrine. Microsoft’s legal team drew parallels to older technologies, arguing in a filing that “Copyright law is no more an obstacle to the LLM than it was to the VCR (or the player piano, copy machine, personal computer, internet, or search engine).”
OpenAI has also claimed The Times “hacked” ChatGPT to deliberately provoke it into generating near-verbatim excerpts for the lawsuit. The Times’ legal team has dismissed these defenses, with attorney Ian Crosby stating in a January 2025 hearing that the AI’s function is “about replacing the content, not transforming it.”
The core of the dispute was allowed to proceed toward trial in March 2025, when a judge dismissed secondary claims but kept the main copyright infringement allegations intact. At the time, Times attorney Steven Lieberman said, “We appreciate the opportunity to present a jury with the facts about how OpenAI and Microsoft are profiting wildly from stealing the original content of newspapers across the country.”
Litigation vs. Licensing: A Divided Media Landscape
While aggressively pursuing litigation, The New York Times has simultaneously embraced a dual strategy. In a move that highlights the complex financial realities of the media industry, the company announced a major content licensing deal with Amazon in May 2025.
Meredith Kopit Levien, CEO of The Times, framed the agreement as a way to ensure its journalism is properly valued. She stated, “The deal is consistent with our long-held principle that high-quality journalism is worth paying for,” underscoring the publisher’s pragmatic approach to monetizing its content in the AI era.
This strategy reveals a deep schism in the publishing world. Some media outlets, including TIME, The Atlantic, and Vox Media, have opted for collaboration, signing lucrative licensing deals with OpenAI. These partnerships offer a revenue stream and a seat at the table with AI developers.
Others, however, are joining The Times on the legal front. The publisher has also targeted smaller firms, sending a cease and desist letter to Perplexity AI in October 2024 over similar copyright concerns. The outcome of these legal battles could fundamentally reshape the relationship between AI developers and content creators for years to come.
