In a landmark legal action that could fundamentally alter how artificial intelligence companies access and utilize news content, the Chicago Tribune filed a federal copyright infringement lawsuit against Perplexity AI on December 4, 2024. This legal challenge targets not just the training of AI models but the very technology that powers modern AI search engines: Retrieval Augmented Generation (RAG). As the lawsuit unfolds in the U.S. District Court for the Southern District of New York, it raises critical questions about the future of AI-powered information retrieval and the survival of journalism in the digital age.
Understanding the Chicago Tribune Lawsuit Against Perplexity
The Chicago Tribune’s lawsuit represents a strategic escalation in the ongoing conflict between traditional media organizations and artificial intelligence companies. Filed in the U.S. District Court for the Southern District of New York, the complaint alleges that Perplexity AI has engaged in massive copyright infringement by unlawfully copying and distributing Tribune content through its AI-powered search engine and recently launched Comet browser.
According to the complaint, Tribune lawyers contacted Perplexity in mid-October 2024 to inquire whether the AI search engine was using its content. Perplexity’s lawyers responded that the company did not train its models with Tribune’s work but acknowledged that it “may receive non-verbatim factual summaries.” The Tribune disputes this characterization, arguing that Perplexity’s outputs are often identical or substantially similar to original Tribune content.
The lawsuit specifically targets Perplexity’s use of Retrieval Augmented Generation technology, marking one of the first major legal challenges to real-time content retrieval systems rather than just training data practices. The Tribune alleges that Perplexity bypasses paywalls to access premium subscriber content and then reproduces this material in ways that directly compete with the newspaper’s original articles.
Mitch Pugh, Executive Editor of the Chicago Tribune, issued a strong statement about the lawsuit: “The Perplexity business model is based on the theft of journalism created by real live journalists at the Chicago Tribune and other publications. Journalists who work each day to serve the public interest, seeking justice and holding power accountable often at great personal and institutional risk. Any accurate information that Perplexity provides to users is based entirely on this work. It is stealing, plain and simple.”
What is Perplexity AI and Why Does It Matter?
Founded in 2022 by Aravind Srinivas, Denis Yarats, Johnny Ho, and Andy Konwinski, Perplexity AI has emerged as one of the fastest-growing artificial intelligence startups in Silicon Valley. The company positions itself as an “answer engine” rather than a traditional search engine, providing users with direct, comprehensive responses to queries instead of simply listing relevant links.
Perplexity’s rapid growth trajectory has been remarkable. The company started 2024 with a valuation of approximately $520 million and reached $20 billion by September 2024 after raising $200 million in new capital. The startup has raised a total of $1.5 billion in funding from prominent investors including Jeff Bezos, Nvidia, SoftBank’s Vision Fund 2, New Enterprise Associates, and IVP. As of May 2025, Perplexity processes approximately 780 million queries monthly, with more than 20% month-over-month growth, handling around 30 million queries daily.
The company’s technology differentiates itself from Google Search by combining large language models with real-time web retrieval. When users ask questions, Perplexity searches the internet for current information, synthesizes findings from multiple sources, and presents a single comprehensive answer with citations. This approach aims to eliminate the need for users to click through multiple websites to gather information.
In October 2024, Perplexity launched Comet, an AI-powered browser built on Chromium. The browser integrates Perplexity’s search engine directly into the browsing experience, enabling users to generate article summaries, conduct research, and perform various tasks without leaving the browser environment. The Tribune’s lawsuit alleges that Comet specifically enables users to bypass paywalls and access premium content without authorization.
Perplexity has attempted to address concerns about content usage through its Publishers’ Program, launched in July 2024. This revenue-sharing initiative partners with publications including TIME, Fortune, Der Spiegel, and others, allocating portions of advertising revenue when their content is sourced. In August 2024, Perplexity also launched Comet Plus, dedicating 80% of its $5 monthly subscription fee to participating publishers. However, the Tribune and many other major publishers have not joined these programs, arguing they do not adequately compensate copyright holders for the use of their work.
The Revolutionary Technology at the Center: RAG Explained
Retrieval Augmented Generation represents a fundamental advancement in how artificial intelligence systems access and process information. Understanding RAG is essential to grasping why the Chicago Tribune lawsuit could have far-reaching implications for the entire AI industry.
RAG operates through a multi-stage process that differs significantly from traditional AI model training. First, in the ingestion phase, documents and data are converted into numerical representations called embeddings or vectors and stored in specialized databases. When a user submits a query, the system converts this question into a vector representation and searches the database for relevant matches. The most pertinent information is then retrieved and combined with the user’s original query to create an augmented prompt that provides context for the AI model. Finally, the large language model generates a response based on both its training data and the freshly retrieved information.
This approach offers several advantages over standard AI models. RAG systems can access information published after the model’s training cutoff date, ensuring responses reflect current events and developments. Organizations can incorporate proprietary or specialized knowledge without expensive model retraining. The technology reduces AI hallucinations by grounding responses in verified source material. Companies can update information simply by adding new documents to the knowledge base rather than retraining entire models.
The 2020 paper that introduced RAG described it as a “general-purpose fine-tuning recipe” that could enhance nearly any large language model with external resources. Patrick Lewis, the lead author who now works at AI startup Cohere, has noted that the technique can be implemented with as few as five lines of code, making it accessible and cost-effective for developers.
However, RAG also introduces new legal questions that courts have not yet addressed. Unlike training data that becomes embedded in model parameters during one-time training, RAG systems continuously retrieve and process copyrighted content in real-time. This distinction is crucial: traditional copyright lawsuits against AI companies like OpenAI and Anthropic focus on whether using copyrighted material for training constitutes fair use. The Tribune’s lawsuit against Perplexity asks a different question: does retrieving, summarizing, and presenting copyrighted content through RAG constitute infringement, even if the content was never used for training?
The Tribune’s Legal Arguments and Allegations
The Chicago Tribune’s complaint presents multiple distinct allegations against Perplexity AI, each targeting different aspects of how the company’s technology operates and impacts the newspaper’s business.
The lawsuit alleges that Perplexity generates outputs that are “identical or substantially similar to the Chicago Tribune’s content.” According to the complaint, upon information and belief, Perplexity has unlawfully copied millions of copyrighted Tribune stories, videos, images, and other works to power its products and tools. The Tribune contends that Perplexity’s RAG system relies on Tribune articles as a live data source, continuously accessing and processing this content to answer user queries.
One of the most significant allegations concerns paywall circumvention. The Tribune argues that Perplexity’s Comet browser performs an “end run around paywalls” to generate detailed summaries of subscriber-only content. This is particularly damaging to the Tribune’s business model, which depends heavily on subscription revenue. By providing comprehensive summaries of paywalled articles, Perplexity allegedly eliminates the incentive for users to purchase Tribune subscriptions or visit the newspaper’s website.
Until recently, Perplexity actively marketed its ability to help users “skip the links,” encouraging people to rely exclusively on Perplexity’s summaries rather than visiting source websites. This marketing message directly contradicts the company’s current defense that it serves as a discovery tool that drives traffic to publishers. The Tribune’s complaint highlights this messaging as evidence of Perplexity’s intent to substitute for, rather than complement, original journalism.
The lawsuit also addresses the problem of AI hallucinations. Like many AI systems, Perplexity sometimes generates inaccurate or fabricated information. When these hallucinations occur, Perplexity often attributes them to sources like the Chicago Tribune, potentially damaging the newspaper’s reputation for accuracy and reliability. The complaint argues that readers who encounter false information attributed to the Tribune may lose trust in the publication, causing long-term harm to its brand.
Beyond copyright infringement, the Tribune argues that Perplexity’s actions threaten the economic foundation of journalism. The complaint states: “By copying the Chicago Tribune’s copyrighted content and using it to create substitutive output derived from its works, obviating the need for users to visit the Chicago Tribune’s website or purchase its newspaper, Perplexity is misappropriating substantial subscription, advertising, licensing, and affiliate revenue opportunities that belong rightfully and exclusively to the Chicago Tribune.”
This economic argument extends beyond immediate revenue losses. The Tribune contends that if news organizations cannot control the use of their content and monetize it effectively, they will have fewer journalists able to dedicate time and resources to important, in-depth stories. This creates a risk that critical journalism serving the public interest will go untold, harming democracy and informed citizenship.
The New York Times Joins the Legal Battle
Just one day after the Chicago Tribune filed its lawsuit, the New York Times escalated the conflict by filing its own copyright infringement suit against Perplexity on December 5, 2024. The Times lawsuit adds significant weight to the legal campaign against AI content scraping and strengthens the argument that Perplexity’s business model systematically violates copyright protections.
The Times complaint alleges that Perplexity engaged in “large-scale, unlawful copying and distribution” of its content, threatening both the newspaper’s reputation and its ability to support journalism. According to Graham James, a Times spokesperson: “While we believe in the ethical and responsible use and development of AI, we firmly object to Perplexity’s unlicensed use of our content to develop and promote their products. We will continue to work to hold companies accountable that refuse to recognize the value of our work.”
The Times lawsuit reveals a contentious history between the two organizations. The newspaper sent Perplexity a cease-and-desist notice in October 2024, demanding that the company stop accessing and using Times content. According to the complaint, the Times issued another notice in July 2025, but Perplexity continued to access and use its content without authorization. The lawsuit claims that the Times engaged in negotiations with Perplexity for more than 18 months, attempting to reach a licensing agreement, but the company persisted in using Times content throughout this period.
Similar to the Tribune’s allegations, the Times complaint accuses Perplexity of copyright infringement at two distinct stages. First, by scraping the Times website in real-time to train AI models and feed content into products like the Claude chatbot and Comet browser. Second, in the output phase, where the Times alleges Perplexity’s generative AI products reproduce Times articles “verbatim or near-verbatim.”
The Times also emphasizes the reputational damage caused by AI hallucinations. The lawsuit claims Perplexity’s system creates fabricated content and falsely attributes these “hallucinations” to the Times, displaying them alongside the newspaper’s registered trademarks. This association of the Times brand with inaccurate information undermines decades of work building trust with readers.
The Times complaint notes that the newspaper has pursued a dual strategy regarding AI companies. While suing Perplexity and OpenAI for copyright infringement, the Times has established licensing agreements with companies willing to compensate it for content use, including a multi-year deal with Amazon earlier in 2024. This approach demonstrates that the Times is not opposed to AI technology itself but insists on proper licensing and compensation for the use of its journalism.
Perplexity Faces Multiple Legal Challenges
The lawsuits from the Chicago Tribune and New York Times represent just two fronts in a growing legal war against Perplexity AI. The company faces at least five separate legal actions from various organizations, each raising concerns about how it accesses and uses copyrighted content.
Dow Jones & Company, publisher of the Wall Street Journal, along with the New York Post, filed a lawsuit against Perplexity in October 2024. This suit alleges that Perplexity engaged in a “massive amount of illegal copying” of copyrighted works, diverting customers and revenues from the publishers. The Dow Jones complaint was amended on December 11, 2024, strengthening its allegations and asserting copyright infringement, false designation of origin, and trademark dilution claims. A judge recently rejected Perplexity’s motion to dismiss the case, allowing it to proceed toward trial.
The Dow Jones lawsuit emphasizes the economic harm to journalism. The complaint argues that news organizations invest significant resources in investigative reporting under tight deadlines and unpredictable circumstances. They rely on subscription and advertising revenue to underwrite journalism costs. When AI systems like Perplexity provide comprehensive summaries that substitute for original articles, they undercut these revenue streams and threaten the viability of professional journalism.
In October 2024, Reddit filed a federal lawsuit in New York against Perplexity and three other companies, alleging they unlawfully scraped Reddit’s user-generated content. This lawsuit highlights a broader pattern of alleged data collection without authorization. Separate investigations by Wired magazine and web developer Robb Knight found that Perplexity does not respect the Robot Exclusion Protocol (robots.txt), a web standard that allows website owners to specify which parts of their sites should not be scraped by automated tools.
According to these investigations, Perplexity uses undisclosed web crawlers with spoofed user-agent strings to scrape content from news websites that explicitly block web scraping. When confronted about these findings, Perplexity CEO Aravind Srinivas suggested the company relies on third-party web crawlers and declined to commit to stopping the scraping of content from sites like Wired.
In August 2024, two Italian media companies owned by the Berlusconi family, RTI and Medusa Film, sued Perplexity in Rome. This lawsuit represents Italy’s first copyright case targeting alleged violations linked to AI training, accusing Perplexity of using copyrighted films and TV programs without permission to train its systems.
Beyond lawsuits, Perplexity has faced threats of legal action from other major companies. In November 2024, Amazon sent Perplexity a cease-and-desist letter over the company’s AI browser shopping agents, which Amazon alleged were improperly making purchases on its platform. In June 2025, the BBC threatened legal action, demanding that Perplexity stop unauthorized scraping of BBC content and delete all retained BBC material.
Perplexity’s Defense Strategy and Response
Perplexity AI has adopted a confrontational stance in response to the lawsuits, characterizing publishers as adversaries of technological progress. Jesse Dwyer, Perplexity’s head of communication, stated: “Publishers have been suing new tech companies for a hundred years, starting with radio, TV, the internet, social media and now AI. Fortunately it’s never worked, or we’d all be talking about this by telegraph.”
This response draws a historical parallel between current AI disputes and past conflicts when new technologies disrupted existing media business models. The company suggests that legal resistance to innovation has consistently failed, implying that AI-powered search represents inevitable progress that publishers cannot stop through litigation.
In an October 2024 blog post addressing the Dow Jones lawsuit, Perplexity elaborated on this position: “The common theme betrayed by those complaints collectively is that they wish this technology didn’t exist. They prefer to live in a world where publicly reported facts are owned by corporations, and no one can do anything with those publicly reported facts without paying a toll. That is not our view of the world.”
This argument frames the dispute as fundamentally about whether facts themselves can be owned, rather than whether specific expressions of those facts receive copyright protection. Perplexity contends it provides “a fundamentally transformative way for people to learn facts about the world” and that its approach is not only legal but “essential for the sound functioning of a cultural ecosystem.”
However, Perplexity’s legal defense faces significant challenges. The company’s response to the Tribune’s inquiry that it “may receive non-verbatim factual summaries” acknowledges that it accesses content in some form, even while denying that it uses Tribune work for model training. This distinction between training and real-time retrieval may prove legally significant, but it does not necessarily shield Perplexity from copyright liability.
The company’s previous marketing message to “skip the links” undermines its current argument that it drives traffic to publishers. If Perplexity designed its service specifically to replace rather than complement original sources, courts may view this as evidence of intent to substitute for copyrighted works rather than provide fair use transformation.
Perplexity has attempted to address publisher concerns through commercial arrangements. The company launched its Publishers’ Program in July 2024, offering revenue sharing with participating outlets including TIME, Fortune, and Der Spiegel. Perplexity has emphasized its willingness to work with publishers and claimed that its “door is always open” for commercial partnerships.
However, major publishers like the New York Times, Chicago Tribune, Wall Street Journal, and New York Post have declined to join these programs, arguing they do not adequately compensate copyright holders. The existence of some publisher partnerships may help Perplexity argue good faith, but it does not resolve the legal question of whether the company can use content from non-participating publishers without authorization.
The Broader Context: Media Organizations vs. AI Companies
The lawsuits against Perplexity represent one battle in a much larger war between content creators and artificial intelligence companies. As of December 2024, more than 40 copyright cases involving AI companies and copyright holders are pending in U.S. courts, with billions of dollars and the future of both industries at stake.
The New York Times filed a landmark lawsuit against OpenAI and Microsoft in December 2023, alleging that the companies trained their AI models on millions of Times articles without permission or compensation. That case remains ongoing and could set crucial precedents for whether using copyrighted material for AI training constitutes fair use. OpenAI has argued that its use of publicly available data for training falls under fair use doctrine, while simultaneously accusing the Times of manipulating ChatGPT to generate problematic examples for the lawsuit.
A coalition of 17 newspapers owned or operated by MediaNews Group and Tribune Publishing filed lawsuits against OpenAI and Microsoft in two separate actions. Eight publications sued in April 2024, and nine more filed suit in November 2024. These cases, ongoing in New York federal court, allege that the AI companies used articles “without permission and without payment” to drive their generative AI programs. Frank Pine, executive editor of MediaNews Group, stated: “OpenAI and Microsoft have built their AI products and models on a massive foundation of stolen material. Even worse, their products are undercutting the business model for news by paraphrasing, plagiarizing and outright regurgitating the news content they have stolen and continue to steal.”
Beyond newspapers, other content creators have pursued legal action against AI companies. Authors and publishers sued Anthropic for using pirated books to train its models. In September 2024, Anthropic agreed to pay $1.5 billion to settle this class action lawsuit, representing the largest publicly reported copyright recovery in AI-related litigation to date. This settlement could influence how courts view other AI copyright cases, particularly regarding the distinction between lawfully acquired training data and pirated or unauthorized content.
In September 2024, Rolling Stone parent company Penske Media became the first major publisher to sue Google over its AI Overviews feature. The lawsuit claims that Google uses journalism without permission to train and display AI summaries, significantly reducing publisher referral traffic. This case highlights concerns that AI-powered summaries, even when provided by traditional search engines, may cannibalize the traffic that publishers depend on for advertising revenue.
Not all interactions between media companies and AI firms have been adversarial. Several major publishers have negotiated licensing agreements with AI companies, recognizing both the inevitability of the technology and the opportunity to secure revenue streams. OpenAI has struck licensing deals with multiple media companies including the Associated Press, Axel Springer (owner of Business Insider and Politico), and News Corp (despite News Corp’s separate litigation over unauthorized use).
The New York Times, while suing OpenAI and Perplexity, established a licensing partnership with Amazon in 2024, allowing Amazon to use Times content for training AI products like Alexa. Hearst, parent company of the San Francisco Chronicle, secured a content partnership with OpenAI. These arrangements demonstrate that publishers are willing to work with AI companies when they receive appropriate compensation and maintain control over how their content is used.
The Economic Impact on Journalism
The legal disputes between publishers and AI companies reflect deeper existential concerns about the future of journalism in an AI-dominated information landscape. Understanding these economic pressures is essential to grasping why organizations like the Chicago Tribune view the Perplexity lawsuit as a fight for survival rather than merely a copyright dispute.
American journalism has experienced devastating economic decline over the past two decades. According to Pew Research Center, newspaper newsroom employment has declined by more than half since the late 2000s. This job loss represents tens of thousands of experienced journalists who no longer produce the investigative reporting, local coverage, and accountability journalism that democracies require.
The traditional business model that supported journalism for over a century has collapsed. Print advertising revenue, which once funded large newsrooms, has largely migrated to digital platforms dominated by Google and Facebook. While some newspapers have successfully built digital subscription businesses, these rarely generate revenue comparable to their print heyday. Local and regional newspapers have been hit hardest, with many closing entirely or reducing staff to skeleton crews.
AI-powered summarization poses a new threat to the fragile economics of digital journalism. Publishers have spent years training readers to accept digital subscriptions and click-based advertising as replacements for print revenue. However, this model depends on users actually visiting publisher websites to read articles. When AI systems like Perplexity provide comprehensive summaries that eliminate the need to visit original sources, they threaten the page views and engagement metrics that underpin digital advertising rates.
Subscription models face similar threats from AI summarization. Why would readers pay for access to articles they can read in summarized form for free through Perplexity or similar services? The Tribune’s allegation that Perplexity bypasses paywalls is particularly damaging because it suggests the company specifically targets premium content that represents publishers’ most valuable subscription offerings.
The harm extends beyond immediate revenue losses. When AI companies use journalistic content without compensation, they create a parasitic relationship where all the costs of journalism fall on publishers while AI companies capture much of the value. Publishers employ journalists, pay for investigative resources, assume legal risks, and maintain expensive editorial operations. AI companies then aggregate this expensive content, synthesize it into answers, and serve those answers to users who might otherwise have subscribed to or visited publisher sites.
This dynamic creates what economists call a free-rider problem. If AI companies can access journalism without paying for it, they have no incentive to contribute to its production costs. As publisher revenues decline and newsrooms shrink, less journalism gets produced. Eventually, the information ecosystem that AI companies depend on begins to degrade, harming both journalists and AI users.
The Chicago Tribune’s complaint articulates this concern: “If the Chicago Tribune and its peers cannot control the use of their content, their ability to monetize that content will be harmed. With less revenue, news organizations will have fewer journalists able to dedicate time and resources to important, in-depth stories, which creates a risk that those stories will go untold.”
Potential Legal Outcomes and Their Implications
The Chicago Tribune lawsuit against Perplexity, along with similar cases from other publishers, could reshape the relationship between AI companies and content creators. Several possible legal outcomes exist, each with different implications for the future of AI-powered information services.
If courts rule that RAG systems constitute copyright infringement when accessing and summarizing copyrighted content without permission, it would fundamentally transform how AI search engines operate. Companies like Perplexity might need to negotiate licenses with every publisher whose content they wish to access, similar to how music streaming services must license songs from rights holders. This outcome would significantly increase operational costs for AI companies but ensure compensation flows to content creators.
Alternatively, courts might find that some uses of RAG technology fall under fair use doctrine while others do not. This nuanced outcome could depend on factors like whether AI responses transform the content substantially, the amount of original material reproduced, the commercial nature of the use, and the market effect on the copyrighted work. Such a ruling would require AI companies to carefully balance their technology to stay within fair use boundaries, potentially limiting the comprehensiveness of AI-generated answers.
Courts could also distinguish between RAG systems that train on copyrighted content and those that only access it for real-time retrieval without incorporating it into model parameters. This distinction might allow some RAG applications while restricting others, depending on the technical details of how different systems operate.
Another possible outcome involves courts clarifying the legal status of paywalls. If courts find that circumventing paywalls to access subscriber-only content constitutes a separate violation beyond copyright concerns, it could provide publishers with additional legal tools to protect premium content. The Computer Fraud and Abuse Act and anti-circumvention provisions of the Digital Millennium Copyright Act might apply to paywall bypassing, creating criminal liability in addition to civil copyright violations.
The trademark claims in several lawsuits, particularly regarding AI hallucinations falsely attributed to publishers, could establish liability even if copyright claims fail. If courts find that AI companies harm publisher brands by associating them with fabricated information, it might require disclosure practices or quality controls that increase AI company costs and reduce the substitution effect for original journalism.
Settlement negotiations might produce industry-wide standards before courts issue definitive rulings. AI companies and publishers could agree on technical standards for content attribution, revenue sharing formulas, or licensing frameworks that satisfy both parties. The Publishers’ Program that Perplexity has already launched, while rejected by major publishers, could evolve into something more acceptable if AI companies agree to more favorable terms.
Regardless of specific legal outcomes, these lawsuits are likely to accelerate the licensing deals between AI companies and content publishers. Even companies confident in their legal position may prefer negotiated agreements to lengthy, expensive litigation. The precedent of Anthropic’s $1.5 billion settlement with authors demonstrates that AI companies face substantial financial risk from copyright litigation.
The Technology Industry’s Response and Perspective
The technology sector has responded to publisher lawsuits with a mixture of legal arguments, philosophical objections, and business initiatives. Understanding these perspectives is important for evaluating the legitimacy of different positions in the AI copyright debate.
Tech companies and AI proponents argue that factual information cannot be copyrighted. While specific expressions receive copyright protection, facts themselves remain in the public domain. When Perplexity synthesizes information from multiple sources and presents it in new language, advocates argue this constitutes transformative use that adds value rather than mere copying. This argument draws parallels to how search engines have long displayed snippets of copyrighted content without liability.
Many technologists view AI-powered search as a natural evolution of information access, no different in principle from previous innovations like search engines, RSS feeds, or aggregation services. They note that publishers initially resisted Google Search, claiming it infringed copyrights by displaying text snippets and cached pages. Courts ultimately found search engines provided fair use, and publishers came to depend on Google for traffic. AI advocates argue that current publisher hostility to AI search will similarly prove short-sighted.
The industry emphasizes the benefits that AI search provides to publishers. Perplexity and similar services cite sources and provide links to original articles, potentially driving traffic to publisher sites. The Wall Street Journal ranked Perplexity as the top-performing chatbot in its “Great AI Challenge” comparison, ahead of ChatGPT, Microsoft Copilot, Google Gemini, and Anthropic’s Claude. This performance could expose publishers to audiences who might not otherwise discover their content.
Some AI researchers and entrepreneurs argue that publisher lawsuits threaten innovation and public access to information. They contend that allowing publishers to control how facts are used would create monopolies on knowledge and force users to pay tolls for accessing publicly reported information. This perspective views journalism as a public good that should remain accessible through new and more efficient technologies.
The venture capital community that funds AI startups has a strong financial interest in preserving current business models. With billions of dollars invested in companies like Perplexity, investors worry that adverse legal rulings could eliminate the value of these investments. This financial pressure encourages aggressive legal defense strategies and public messaging that frames publisher concerns as resistance to progress.
However, some within the technology community recognize the legitimacy of publisher concerns. Reid Hoffman, co-founder of LinkedIn and an investor in several AI companies, has advocated for fair compensation models that support journalism while enabling AI innovation. Various proposals have emerged for micro-licensing systems, revenue-sharing arrangements, and technical standards that could balance the interests of AI companies and content creators.
Lessons from Past Technology Disruptions
The conflict between publishers and AI companies echoes similar disputes from previous technological disruptions. Examining these historical precedents provides context for understanding possible outcomes of current litigation.
When video cassette recorders emerged in the 1970s, movie studios sued Sony, arguing that enabling home recording of television broadcasts violated copyright law. The Supreme Court’s 1984 decision in Sony Corp. v. Universal City Studios (the “Betamax case”) established the principle that technology enabling copyright infringement could be legal if it also has substantial non-infringing uses. This precedent has protected technology companies from liability for user actions ever since, though its applicability to AI systems remains uncertain.
The music industry’s battle against file-sharing services in the 2000s offers another instructive example. Services like Napster initially argued they merely facilitated user file sharing and bore no responsibility for copyright infringement. Courts rejected this argument, finding that services designed primarily for infringement shared liability. However, this enforcement action did not restore the music industry’s previous business model. Instead, legal pressure combined with new technologies eventually produced legitimate streaming services like Spotify that compensate rights holders while providing user-friendly access.
Google News faced similar objections from publishers when it launched in 2002. Many publishers argued that displaying headlines and snippets constituted copyright infringement and would reduce traffic to their sites. Some publishers demanded payment for inclusion in Google News, leading to temporary removals and ongoing tensions. However, most publishers eventually recognized that Google News drove significant traffic to their sites and negotiated mutually beneficial arrangements.
The key difference between these precedents and current AI disputes lies in the substitution effect. Video recorders, file-sharing services, and Google News all made content more accessible but generally drove users toward copyrighted works rather than replacing them. AI-powered summarization services potentially eliminate the need to access original works, creating a different economic dynamic that courts may view less favorably under fair use analysis.
International Dimensions and Global Implications
The copyright disputes between publishers and AI companies extend far beyond U.S. courts, with different jurisdictions approaching these questions from varying legal and cultural perspectives.
The European Union has taken a more proactive regulatory approach than the United States through its AI Act, which established comprehensive requirements for AI system development and deployment. The EU regulations include specific provisions for copyright protection and transparency in AI training data. European publishers may have stronger legal protections against unauthorized content use than their American counterparts.
The lawsuit filed by Italian media companies owned by the Berlusconi family represents the first AI copyright case in Italy specifically targeting training data use. Italian copyright law, rooted in author’s rights traditions rather than American copyright’s utilitarian framework, may provide different protections for content creators. The outcome of this case could influence how European courts interpret EU AI regulations and existing copyright directives.
The United Kingdom has considered implementing copyright exceptions that would allow AI companies to use copyrighted material for training without permission unless rights holders opt out. This approach differs significantly from both U.S. fair use doctrine and EU regulations, potentially creating a more permissive environment for AI development. However, strong pushback from creative industries has delayed implementation of these exceptions.
China’s approach to AI regulation emphasizes content control and algorithmic accountability rather than copyright protection. Chinese AI companies face extensive government oversight of output content but may have more flexibility in accessing training data. This could create competitive advantages for Chinese AI companies in terms of data access, though restrictions on content output limit their global appeal.
These varying international approaches create complexity for global AI companies like Perplexity. A system that operates legally in the United States might violate European or Asian regulations, requiring different technical implementations for different markets. This regulatory fragmentation could disadvantage smaller AI companies that lack resources to comply with multiple legal regimes while benefiting larger companies with extensive legal and engineering resources.
What This Means for Content Creators and AI Users
The ongoing legal battles between publishers and AI companies will affect everyone who creates or consumes content online. Understanding the implications for different stakeholders helps clarify what’s at stake in these disputes.
For content creators, the outcome of lawsuits like the Tribune’s action against Perplexity will determine whether they can control how their work is used and receive compensation for that use. If publishers lose these cases, it could accelerate the migration of content creation to walled platforms with technical protections that prevent AI access. Conversely, if publishers prevail, it could establish compensation mechanisms that help sustain journalism and other professional content creation.
Individual journalists and writers face particular uncertainty. Many produce content for platforms they don’t control, leaving them dependent on their employers to negotiate fair terms with AI companies. Freelance creators have even less ability to monitor or control AI use of their work. The possibility of receiving direct compensation through licensing arrangements could provide new revenue streams, but only if legal frameworks require AI companies to track and pay for individual content use.
AI users who have come to depend on services like Perplexity for information access could face reduced functionality or increased costs depending on how legal disputes resolve. If courts require comprehensive licensing arrangements, AI companies might pass these costs to users through higher subscription fees. Alternatively, AI services might become more limited in the content they can access, reducing their usefulness for research and information gathering.
Educational institutions and researchers represent another affected constituency. Many have embraced AI tools for literature reviews, research assistance, and teaching. If AI services become more restricted or expensive, it could limit educational access to these powerful technologies. Conversely, if legal clarity emerges around appropriate AI use, institutions could more confidently integrate these tools into educational and research workflows.
The general public’s access to information hangs in the balance. AI-powered search could democratize knowledge access by making complex information more understandable and accessible. However, if AI companies undermine the economic foundation of journalism by using content without compensation, the long-term result could be less information for everyone. Finding the right balance between AI capabilities and sustainable journalism remains the core challenge these lawsuits must address.
Looking Ahead: The Future of AI Search and Journalism
As the Chicago Tribune lawsuit against Perplexity proceeds through the courts, several scenarios could emerge for how AI search and journalism coexist in the future.
One possible future involves comprehensive licensing arrangements becoming standard practice. Just as music streaming services pay rights holders, AI search engines might negotiate blanket licenses with publishers, paying for access to content based on usage metrics. This would ensure revenue flows to content creators while allowing AI companies to operate without legal uncertainty. The technical infrastructure for tracking content use and distributing royalties exists, though implementing it at scale presents challenges.
Another scenario involves technical solutions that satisfy both parties. AI companies could develop attribution systems that make original sources more prominent, potentially driving traffic back to publishers. Enhanced citation practices, prominent source linking, and compensation tied to user engagement with sources could create a symbiotic rather than parasitic relationship between AI systems and publishers.
The emergence of new business models might resolve current tensions. Publishers could embrace AI-powered distribution as a new channel, developing content specifically optimized for AI presentation alongside traditional articles. Subscription services might evolve to include both direct access to publisher sites and AI-mediated access through services like Perplexity, with revenue sharing arrangements that satisfy all parties.
Regulation could provide the framework for coexistence if market solutions fail. Governments might establish compulsory licensing systems similar to those in music, requiring AI companies to pay for content use based on prescribed formulas. Regulatory bodies could oversee fair compensation while ensuring AI services remain viable. However, the slow pace of regulatory processes means market developments and legal rulings will likely establish norms before comprehensive regulation emerges.
The worst-case scenario involves a breakdown of cooperation that harms both journalism and AI development. If extensive litigation drains resources from both sides without producing clear legal standards, it could delay innovation and accelerate journalism’s decline. Publishers might retreat behind technical barriers that prevent AI access while limiting their audience reach. AI companies might focus on generating synthetic content rather than aggregating human journalism, potentially reducing information quality and diversity.
The most likely outcome involves elements of all these scenarios, with different solutions emerging for different contexts. Major publishers with strong legal resources will negotiate favorable licensing terms, while smaller publications might depend on collective licensing schemes or industry-wide standards. AI companies will adapt their technologies to reduce copyright risk while maintaining functionality, and users will gradually adjust to new ways of accessing information that balance creator compensation with user convenience.
Conclusion: A Defining Moment for Digital Information
The Chicago Tribune’s lawsuit against Perplexity AI represents far more than a single copyright dispute. It poses fundamental questions about knowledge ownership, technological progress, journalism sustainability, and public information access in the AI age. How courts answer these questions will shape the digital information landscape for decades.
The case highlights the tension between two legitimate interests. Publishers like the Chicago Tribune invest enormous resources in producing journalism that serves the public interest. They deserve compensation for their work and protection against technologies that undermine their business models without providing alternatives. Simultaneously, AI technologies like Perplexity offer genuine improvements in how people access and understand information, potentially democratizing knowledge and making complex topics more comprehensible.
The challenge lies in finding frameworks that honor both interests. Copyright law provides some guidance, but RAG technology presents novel questions that existing precedents may not adequately address. The distinction between copying for training and retrieving for real-time generation, the role of paywalls, the impact of AI hallucinations on brand reputation, and the appropriate scope of fair use in AI contexts all require careful judicial or legislative consideration.
Whatever the outcome, the relationship between AI and journalism will inevitably evolve. The question is whether this evolution happens through thoughtful negotiation that sustains both industries or through destructive conflict that diminishes both. The Chicago Tribune lawsuit, along with similar actions by the New York Times, Dow Jones, and others, represents an attempt to force this conversation before market dynamics irreversibly damage journalism.
For Perplexity, the legal challenges threaten a business model that has attracted $1.5 billion in investment and achieved a $20 billion valuation. If courts determine that RAG systems must license content, the company faces either substantially higher costs or significant limitations on functionality. However, if Perplexity prevails or reaches favorable settlements, it could validate an approach to information access that transforms how people interact with knowledge.
The coming months and years will reveal whether litigation produces clarity or further confusion, whether negotiation yields sustainable business models or temporary truces, and whether technology and journalism can coexist productively or only antagonistically. The Chicago Tribune’s decision to sue Perplexity has helped ensure these critical questions receive the attention they deserve. The answers will determine not just the fate of specific companies but the future of journalism, AI development, and public information access in the digital age.
As this landmark case proceeds through the judicial system, it serves as a reminder that technological progress does not happen in a vacuum. New capabilities must be reconciled with existing rights, established industries must adapt without being destroyed, and society must ensure that innovation serves rather than undermines fundamental needs like trustworthy journalism and accessible information. The Chicago Tribune vs. Perplexity lawsuit represents a crucial test of whether these reconciliations can be achieved through legal processes or require alternative solutions.
Sources
This article was researched and compiled using information from the following sources:
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