Chicago Tribune vs. Perplexity: The War Over "Skipping the Links" Just Exploded

If you thought the copyright wars were just about ChatGPT reading books it shouldn't have, buckle up. The battle lines have shifted from training AI to how AI searches the web, and the Chicago Tribune just launched a nuclear strike.

As of yesterday (December 4, 2025), the Chicago Tribune and a coalition of newspapers owned by Alden Global Capital (operating under MediaNews Group) have filed a federal lawsuit against Perplexity AI.

The accusation? It’s not just that Perplexity read their articles to get smart. It’s that Perplexity is allegedly breaking into their house (bypassing paywalls), stealing the furniture (content), and setting up a showroom next door to sell it (RAG-based answers).

Here is the breakdown of the lawsuit that could redefine how we use the internet.

The Core Allegation: "Willful Infringement" via RAG

Most AI lawsuits so far (like The New York Times vs. OpenAI) have focused on training data—the idea that AI companies fed millions of copyrighted articles into their models years ago to teach them English and facts.

This lawsuit is different. It targets RAG (Retrieval-Augmented Generation).

What is the difference?

1. Training: Teaching a student by having them read a library of books once.
2. RAG: A student taking an exam who runs to the library, photocopies a page from a book, and pastes it into their essay in real-time.

The Chicago Tribune alleges that Perplexity isn’t just hallucinating answers; it is actively scraping their live, paywalled content and serving it to users so they never have to visit the actual newspaper website.

The Smoking Gun Claim: The lawsuit targets Perplexity’s "Comet" browser and search engine, alleging they are designed to "skip the links" entirely. The Tribune claims this isn't fair use; it's a "brazen scheme to compete for readers while freeriding on valuable content."

The "Paywall Jailbreak"

Perhaps the most damaging technical accusation is that Perplexity is ignoring standard web protocols (like robots.txt or paywall barriers) to access premium content. The suit claims Perplexity surfaces facts and text from articles that human readers would have to pay to see.

Who is Suing? (The Alden Factor)

It’s important to know who is pulling the trigger here. The plaintiffs aren't just the Chicago Tribune. They are part of Alden Global Capital’s portfolio.

1. The Plaintiffs: Chicago Tribune, New York Daily News, Orlando Sentinel, San Jose Mercury News, and others.
2. The Reputation: Alden is often described by media critics as a "vulture capitalist" firm known for aggressively cutting newsroom costs.

Why this matters: Alden is litigious and financially motivated. They aren't suing for the "soul of journalism" in the poetic sense; they are suing for the asset value of their data. They have already sued OpenAI and Microsoft (April and November 2024). Now, they are coming for the "answer engines."

The Technical Deep Dive: RAG vs. Fair Use

This case will likely hinge on whether RAG constitutes "Fair Use."

The Publisher's Argument

1. Substitution: If Perplexity gives you the answer (extracted from a Tribune article), you have zero reason to click the link.
2. Economic Harm: No clicks = no ad revenue = no subscriptions.
3. Theft: Surfacing 30-50% of an article in a summary isn't "search"; it's republication.

Perplexity’s Likely Defense

While Perplexity hasn't issued a formal legal defense to this specific filing yet (as of this morning), their standard defense (and CEO Aravind Srinivas's previous stance) usually involves:

1. Citations: "We cite the sources prominently."
2. Traffic Driver: "We are actually sending high-intent traffic to these sites."
3. Fact vs. Expression: Copyright protects how you write a story (expression), not the facts within it. If Perplexity summarizes the facts of a fire in Chicago, they argue that's fair game.

Why This is Dangerous for Perplexity

Perplexity is smaller than Google or OpenAI. A massive copyright judgment could cripple them.

Furthermore, this hits Perplexity's specific value proposition. They market themselves as the "anti-Google"—the place you go to get answers fast without wading through SEO spam. If a court rules that "getting answers fast" by scraping news sites is illegal, Perplexity’s entire product mechanics might have to change.

The "Revenue Share" Shield

Perplexity tried to get ahead of this. In late 2024, they launched a Publishers Program to share revenue with partners (like Time, Der Spiegel, etc.).

1. The Problem: The Chicago Tribune and Alden obviously didn't sign up. They chose war instead.

What Happens Next?

This case (filed in the Southern District of New York) will be a slow burn, but the implications are immediate.

1. More Lawsuits: Expect other holdout publishers to join the pile-on if the Tribune survives the first motion to dismiss.
2. Geoblocking Risk: We might see a scenario where Perplexity simply stops indexing certain publishers to avoid liability, making the AI search engine "dumber" but legally safer.
3. The "snippet" debate: The courts will finally have to decide: How much text can an AI show before it becomes theft? Is it 5 words? 50 words? Or a full bulleted summary?

Verdict

The Chicago Tribune isn't just suing for money; they are suing to establish a boundary for the AI age. If they win, the "free lunch" of AI search is over. If they lose, the traditional news business model might effectively be dead.