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OpenAI has offered some media firms as little as between $1 million and $5 million annually to license their news articles for use in training its large language models, according to two executives who have recently negotiated with the tech company. That’s a tiny amount even for small publishers, which could make it difficult for OpenAI to strike deals.

Meanwhile, Apple, which is trying to catch up to OpenAI and Google in the generative artificial intelligence sector, is also trying to strike deals with publishers for use of their content, said one executive. Apple is offering more money but also wants the right to use content more widely than what OpenAI is seeking, according to a person familiar with the matter. Apple wants to be able to use content for future AI products in any way the company deems necessary, this person said.

For some in the industry, the efforts by OpenAI and Apple to negotiate AI licensing deals recall deals struck in the past decade by tech firms such as Facebook, now known as Meta Platforms, and Google to license news content for use on social media and in search. Those deals have left some publishers feeling burned, particularly as Facebook has reduced the importance it puts on news and has cut back on what it pays, hurting media businesses that had come to depend on the payments and traffic. That experience has prompted publishers to approach recent negotiations cautiously, ensuring they get good value for their content.

Last week The New York Times Co. sued OpenAI and its partner, Microsoft, which uses OpenAI’s tech in its products, for copyright infringement. The Times said in the lawsuit that it had tried to negotiate an agreement to “ensure it received fair value for the use of its content,” but the negotiations hadn’t led to a resolution. More such lawsuits are likely, predicted one executive this week.

OpenAI said in a statement that it respected "the rights of content creators and owners and are committed to working with them to ensure they benefit from AI technology and new revenue models." The company said it was "surprised and disappointed" by the Times' lawsuit and are "hopeful that we will find a mutually beneficial way to work together, as we are doing with many other publishers.”

OpenAI is holding talks with as many as a dozen publishers, executives say, hoping to strike deals similar to those it has already done with Axel Springer, publisher of Politico and Business Insider, and the Associated Press. The owner of ChatGPT has concentrated most recently on negotiating deals with owners of global news publications rather than firms that publish other types of content on subjects such as entertainment and lifestyle, said one executive. Details of the Axel Springer and AP deals couldn’t be learned, but Axel Springer is receiving tens of millions of dollars over several years, according to industry executives. Axel Springer declined to comment and the AP didn't respond to a request for comment.

Publishers may be able to pressure OpenAI to improve its terms by striking deals with rivals such as Apple. In recent weeks, Apple executives have told industry executives they are nearing AI deals with about a dozen media companies, this person said. Apple had offered multiyear deals worth at least $50 million to news organizations including NBC News, Condé Nast, which owns The New Yorker, and IAC, parent company of The Daily Beast, The New York Times reported. Apple didn't respond to a request for comment.

Then there’s Google. The search giant has developed its own LLMs it is rolling out to consumers and corporate customers, but it has fallen behind OpenAI and Apple in negotiating licensing agreements with publishers, a person familiar with the matter said. But Google has deeper ties than OpenAI and Microsoft to publishers through existing products like Google News, a major source of traffic for news sites. It also has bespoke agreements with some publishers, like The New York Times, under which the companies collaborate on distribution and advertising. A Google spokesperson didn’t comment.

AI developers use news content to help power question-and-answer chatbots or handle other information requests. Some of the large AI developers, as well as startups, have trained their LLMs on copyrighted works, AI practitioners say.

The Times is not the only publisher to sue LLM developers over copyright infringement. Comedian Sarah Silverman and other authors in July filed a lawsuit against Meta Platforms, alleging it had ripped off their intellectual property in its development of open-source LLMs. In November, a federal judge dismissed most of their claims, saying it was “nonsensical” to argue that Meta’s models couldn’t function without the information from the authors’ books.

The Times has a more compelling case than the other plaintiffs suing OpenAI because of the verbatim examples the publisher filed with the court, said Geoffrey Manne, president and founder of the International Center for Law and Economics, a think tank that advocates for policies promoting economic growth.

Because The New York Times registers all its printed articles with the U.S. Copyright Office, it’s entitled to higher penalties, or statutory damages, from copyright violators than an online publisher. With millions of registered articles, The Times could force OpenAI to pay it more than $750 million in damages.