Media Briefing: What The Washington Post’s deal with OpenAI says about the future of AI content licensing

This week’s Media Briefing looks at The Washington Post’s deal with OpenAI to use the news org’s content in its ChatGPT search product, and what it says about the future of licensing deals between AI companies and publishers.

  • Deals between AI companies and publishers are subtly moving toward content for search.
  • Trump’s first 100 days battling the press, news outlets’ shift to podcast videos and more.

The evolution of AI content licensing deals

The Washington Post has become the latest major publisher to strike a licensing deal with OpenAI, joining a growing cohort that now spans more than 20 news organizations. 

It’s part of a familiar pattern: every few months, OpenAI locks in another publisher to bolster its content pipeline. But the terms of these agreements seem to be quietly evolving — subtly shifting away from the explicit language around training data that defined earlier deals, and raising fresh questions about what these partnerships now mean.

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With 600 million users, X’s Linda Yaccarino doubles down on dismissing journalism

Linda Yaccarino continues to cast X as the anti-media media company — a disruptive alternative to what she and Elon Musk believe is the dusty, broke fourth estate.

It’s a contentious claim, especially in an era when President Donald Trump is once again at war with the press. But sitting for a fireside chat with Anthony Pompliano, creator of From the Desk of Anthony Pompliano, on X at Possible this afternoon in Miami, Yaccarino insisted the platform’s (self-reported) numbers back her up.

According to the platform’s CEO, X has nearly amassed 600 million monthly active users (MAUs) globally — a small increase on the 586 million MAUs that were reported in X’s own tools in January, but not a huge increase on the 570 million MAUs X claimed it had reached back in September 2024.

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