New York Times Signs AI Deal With Amazon While Suing OpenAI

There's something beautifully absurd about The New York Times announcing its first AI licensing deal with Amazon on the same day their lawyers are presumably billing hours for their ongoing copyright lawsuit against OpenAI. It's like watching someone sell lemonade to one neighbor while calling the police on another for stealing lemons from the same tree.

The Gray Lady just inked a multi-year agreement to license editorial content from The New York Times, NYT Cooking, and The Athletic to Amazon for "AI-related uses." This includes real-time summaries within Amazon products like Alexa and training Amazon's proprietary foundation models. Meanwhile, their legal team continues pursuing OpenAI and Microsoft for allegedly using their content without permission to train competing AI systems.

Welcome to the media industry's schizophrenic approach to artificial intelligence—simultaneously embracing and rejecting the same technology depending on who's writing the checks.

The Great AI Copyright Casino

The Times deal crystallizes the fundamental tension plaguing every content creator in 2025: Do you fight the AI revolution or profit from it? The answer, apparently, is both.

Under the Amazon agreement, The New York Times will make their journalism "more accessible to customers across Amazon products and services," with direct links back to Times products. It's a controlled, compensated distribution model that theoretically benefits both parties—Amazon gets high-quality training data and real-time content, while the Times gets paid and maintains attribution.

Compare that to their OpenAI lawsuit, where they're arguing that using their content without permission or compensation violates copyright law. The legal complaint specifically targets the unauthorized use of Times articles to train ChatGPT and other models that could potentially compete with their journalism.

The distinction matters, but it also reveals how arbitrary these partnerships have become. OpenAI's crime wasn't necessarily using Times content—it was using it without paying for the privilege.

The Licensing Lottery

This deal represents a seismic shift in how legacy media approaches AI partnerships. For years, publishers watched helplessly as tech giants scraped their content for free, using it to train models that could potentially replace human journalism. Now they're discovering they can monetize what was previously being stolen.

The Times isn't alone in this strategy. Publishers across the industry are taking "different tacks," as the article notes—some signing licensing deals, others heading to court. What we're witnessing is the emergence of a two-tier system: companies that pay for content access, and those that face legal consequences for taking it without permission.

But here's the uncomfortable reality: The same Times content that Amazon is now paying to license was likely already used to train competing AI models years ago. OpenAI, Google, and others built their foundational systems by ingesting massive amounts of web content, including news articles, without explicit permission. The legal battles happening now are essentially about retroactive compensation and future access rights.

The Fair Use Fiction

At the heart of this mess lies the concept of "fair use"—a legal doctrine that allows limited use of copyrighted material for purposes like criticism, comment, or research. AI companies have argued that training models constitutes fair use, while content creators insist it's wholesale theft.

The stakes couldn't be higher. AI companies want "looser restrictions on copyright rules in order to grow and compete globally," while copyright owners including "the Hollywood creative community have pushed back, insisting that the laws be upheld."

The Times-Amazon deal essentially sidesteps this entire debate by creating a commercial framework that makes fair use irrelevant. Why argue about legal doctrines when you can just pay for access?

The Revenue Reality Check

What's fascinating about the Times strategy is how it reveals the economic pressures facing traditional media. They're not licensing content to Amazon out of altruism—they're doing it because AI companies represent a new revenue stream in an industry that's been hemorrhaging money for decades.

The deal brings "additional value to Amazon customers and brings Times journalism to wider audiences," but let's be honest about what's really happening: The Times is monetizing their content archive in ways that were impossible before AI. Every training cycle, every real-time summary, every Alexa response powered by Times content potentially generates revenue.

This is particularly shrewd given the media industry's ongoing struggles with digital advertising and subscription models. If AI companies are going to use journalism to train their models anyway, publishers might as well get paid for it.

The Copyright Office Chaos

Adding another layer of complexity, the article mentions "turmoil at the U.S. Copyright Office" with Trump administration potentially firing the register of copyrights. This institutional uncertainty makes private licensing deals even more attractive—why wait for regulatory clarity when you can negotiate terms directly?

The timing isn't coincidental. As copyright law struggles to keep pace with AI development, forward-thinking publishers are creating their own frameworks for content licensing. The Times-Amazon deal could become a template for how other media companies approach AI partnerships.

The Competitive Contradiction

Perhaps the most delicious irony is that Amazon's Alexa will now provide Times-powered responses while the Times simultaneously argues that OpenAI's similar use constitutes copyright violation. The difference is purely transactional—Amazon paid, OpenAI didn't.

This creates a weird competitive dynamic where the quality of AI responses increasingly depends on licensing deals rather than technological innovation. Amazon's foundation models get access to premium Times content, while competitors face potential legal challenges for using similar material.

We're essentially watching the emergence of an AI content aristocracy, where the best training data goes to the highest bidders.

The Future of Information

The broader implications extend far beyond media economics. If high-quality journalism becomes exclusively available to AI companies that can afford licensing deals, we risk creating information inequality at a foundational level. Some AI systems will be trained on premium, fact-checked content, while others rely on whatever they can scrape for free.

This could exacerbate existing concerns about AI accuracy and bias. When foundation models are trained on different quality datasets based on commercial relationships rather than informational value, the resulting AI systems may reflect those disparities.

The Bottom Line

The New York Times isn't being hypocritical—they're being pragmatic. In a world where AI companies are going to use their content regardless, they're choosing to profit from controlled partnerships while fighting unauthorized use through the courts.

It's a smart strategy that acknowledges the reality of AI development while protecting their economic interests. But it also reveals how quickly the information economy is being restructured around AI training needs rather than public benefit.

The Times-Amazon deal isn't just about content licensing—it's about establishing the economic framework for how knowledge gets monetized in the age of artificial intelligence. Every publisher is watching to see if this becomes the template for survival or just another way to delay the inevitable disruption.

Either way, we're witnessing the transformation of journalism from a public service to a private commodity in the AI training economy. The Gray Lady just became a data vendor, and everyone's taking notes.

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