The Chicago Tribune has filed a federal copyright infringement lawsuit against AI-powered search engine Perplexity, accusing the startup of scraping and republishing its articles — often verbatim or in close paraphrase — through Perplexity’s retrieval-augmented generation (RAG) system and Comet browser, which reportedly bypasses the newspaper’s paywall. The complaint argues that by delivering Tribune content without permission, Perplexity undercuts the paper’s advertising, subscription, and licensing revenue, effectively monetizing journalism it did not produce. The case is part of a wider legal push by legacy media outlets, including The New York Times, with each demanding damages and regulatory clarity over how AI companies handle copyrighted content.
Sources: American Bazaar Online, Reuters
Key Takeaways
– The Chicago Tribune argues that Perplexity’s use of the Tribune’s content via RAG and paywall-bypassing tools constitutes unlicensed reproduction rather than fair use or aggregation.
– This lawsuit joins a growing wave of legal actions by major media organizations — including The New York Times — challenging how AI platforms access, reuse, and profit from proprietary journalism.
– The outcome could reshape how AI-driven tools handle copyrighted content, potentially forcing licensing models or stricter restrictions on scraping and redistribution.
In-Depth
The lawsuit launched by the Chicago Tribune marks a significant escalation in the ongoing confrontation between traditional journalism outlets and emerging AI companies. Perplexity, a startup that has rapidly gained prominence as a generative-AI search engine and content summarization tool, is being accused of crossing a line from aggregation into outright reproduction of copyrighted material — namely, news articles written by Tribune journalists. According to the complaint, Perplexity’s RAG (retrieval augmented generation) system pulls in Tribune articles — sometimes bypassing paywalls via Perplexity’s Comet browser — then repackages them for users, often in verbatim or near-verbatim form. This isn’t a transformation or citation; it’s wholesale re-publication performed by an AI.
For the Tribune, the stakes are more than academic. The lawsuit frames this not as a copyright technicality, but as an existential threat to journalism’s business model. By redistributing its content without permission, Perplexity allegedly diverts traffic, subscriptions, ad views, and licensing opportunities away from the Tribune and toward itself. In effect, the startup would be profiting from the newspaper’s reporting without contributing to its costs. That matters because journalism — especially deep investigative work and local reporting — already struggles to stay afloat financially without predatory AI undercutting value.
This case follows a broader wave of legal challenges by media organizations against AI companies. Notably, the New York Times also filed suit against Perplexity, claiming large-scale unauthorized copying of its content. With multiple outlets — including newspapers, encyclopedias, and other publishers — now suing, the issue has moved beyond isolated disputes. Courts are about to weigh whether practices like RAG, which overlay AI-generated summaries on scraped content, qualify as fair use or represent new, unlicensed distribution of creative work.
The implications are enormous. If the courts side with the media, AI companies may need to adopt new licensing models — paying publishers for access or incorporating revenue sharing. They may be forced to rethink how they build tools, especially those aimed at summarizing or repackaging third-party content. The web could shift from a seemingly open resource to a more gated environment, where content’s value and ownership are reestablished for the AI age. On the flip side, if AI companies prevail, the value of original journalism could be further eroded, pushing more outlets toward collapse and undermining the financial viability of independent reporting.
In short: this isn’t just a lawsuit about copyright — it’s a fight over who controls the future of information. And whichever way the court rules could define the relationship between journalism, technology, and public knowledge for years to come.

