IP Law Daily, COPYRIGHT NEWS: New York Times and Chicago Tribune join the fray against Perplexity AI, (Dec 5, 2025)

By Matthew Hersh, J.D.

The news media companies accuse Perplexity of copyright and trademark violations.

A popular artificial intelligence company unlawfully purloined articles published in the New York Times and the Chicago Tribune when it used those articles to train its large language models and reproduced portions of the text of those articles in response to user queries, two new complaints assert. The matching pair of lawsuits, filed by the same legal team a day apart in the Manhattan federal court, are the latest in a long line of media company lawsuits against artificial companies in the last two years. (New York Times Company v. Perplexity AI, Inc., No. 1:25-cv-10106 filed Dec. 5., 2025) (Chicago Tribune Co., LLC v. Perplexity AI, Inc., No. 1:25-cv-10094 (S.D.N.Y. filed Dec. 4, 2025)).

The two lawsuits revolve around Perplexity AI, the owner and operator of a namesake chatbot that it describes as “answer engine.” When users ask the chatbot questions, Perplexity’s website describes, “it uses advanced AI to search the internet in real-time, gathering insights from top-tier sources” and then “distills this information into a clear, concise summary, delivering exactly what you need in an easy-to-understand, conversational tone.

As with other lawsuits against AI companies, the two complaints accuse the chatbot operator of infringing the media companies’ copyrights in two different ways. First, the lawsuits allege, Perplexity infringes the companies’ copyrights by reproducing their content in the course of training their large language models. Second, they assert, Perplexity further infringes when it reproduces “verbatim or near-verbatim reproductions, summaries, or abridgements of the original content” in response to user questions. For example, the New York Times lawsuit asserts, Perplexity cited The Times’s content in 1.7% of outputs.

In addition to its “massive copyright infringement,” the complaints allege, Perplexity also violates trademarks under the Lanham Act when its model generates fabricated content—or makes misleading omissions—that then get attributed to the papers. The same conduct, the complaints assert, constitutes false designations of origin and dilution as it “confuses and deceives Perplexity users into believing that the hallucinations and/or undisclosed omissions are associated with, sponsored by, or approved by” the newspapers.

This is not the first time that Perplexity has been accused of copyright and trademark infringement. For example, the Wall Street Journal and the New York Post sued the company last October, while Brittanica and Merriam-Webster filed a complaint in October of this year. The New York Times and The Chicago Tribune have also sued other AI companies, most notably in the December 2023 lawsuit—one of the earliest against the backers of large language model technology—that the New York Times brought against Microsoft and OpenAI.

Perplexity, a recent startup, has rocketed up to the number four market share among AI companies over the past year, although a survey of tech founders and investors last month also ranked it as the “most likely to fail” among major AI companies.

The Cases are No. 1:25-cv-10106 and No. 1:25-cv-10094.

Attorneys: Steven Lieberman (Rothwell, Figg, Ernst & Manbeck, P.C.) for The New York Times Company. Bryan Berkeley Thompson (Ernst & Manbeck, P.C.) for Chicago Tribune Co., LLC.

Companies: The New York Times Company; Chicago Tribune Co., LLC; Perplexity AI, Inc.

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