Plus: How DoorDash became an $85 billion behemoth and won the delivery wars.
Fortune 500 Digest with Alyson Shontell
Saturday, December 6, 2025
Foreword
Alyson Shontell
Editor-in-Chief

It’s “code red” inside OpenAI this week, as the longtime leader in the generative AI race feels its lead slipping away. Google (owned by Alphabet, No. 7) is mercilessly showing its AI strength under Sergey Brin, who has returned to the company he cofounded to make sure his team crushes the competition. The success of Google’s latest Gemini model and the intense competition for business customers are igniting concern among even Sam Altman’s most ardent supporters.

But anyone who did not see this coming has not been paying close enough attention. In January 2023, when Fortune’s Jeremy Kahn wrote our cover story on ChatGPT’s viral launch, he cautioned:

“Google and other titans are hard at work on their own A.I. platforms; and future, more polished software could make ChatGPT look like child’s play. OpenAI may someday find that, much like Netscape’s short-lived browser reign, its breakthrough has opened a door to a future it isn’t part of.”

What’s more, other well-funded startups are beginning to eat into OpenAI’s market share. Some reports show its $183 billion rival Anthropic earning a larger share of enterprise customers. For our latest cover story, Kahn sat down with cofounders Dario and Daniela Amodei (who are siblings and former OpenAI employees). And they were not shy about the do-or-die moment in AI.

“Business should care about bringing in cash, not setting cash on fire, right?” Dario Amodei told Kahn, before swiping at OpenAI: “Can you buy so many data centers that you over-leverage yourself?”

For Altman, the stakes couldn’t be higher. But no one should be rooting against OpenAI either. As our Jim Edwards recently wrote, the global markets are so reliant on AI—and specifically on Altman—to succeed that any serious shortcomings by the most-funded private company in history could lead to a financial reckoning.

Check out Kahn’s story on Anthropic here, and Fortune’s Sharon Goldman on the code-red situation at OpenAI here.

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Catch Up
Fortune 500 C-suite Power Moves
Kohl’s (No. 261) appointed Michael Bender CEO on a permanent basis, effective Nov. 23. Dell Technologies (No. 44) appointed David Kennedy CFO on a permanent basis. Nike (No. 90) appointed Venkatesh Alagirisamy to the newly created role of EVP, COO, effective Dec. 8. Nucor (No. 140) promoted Stephen D. Laxton to President and COO, effective Jan. 1.
And more in this week's Fortune 500 Power Moves.
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Deals & Developments
  • Amazon (No. 2) is considering ending its partnership with the U.S. Postal Service and expanding its own delivery operations as discussions over shipping rates and delivery volumes have stalled, according to the Washington Post. Amazon is the largest customer of the USPS, representing billions in revenue annually.
  • The European Union has opened an investigation into Meta Platforms (No. 22) over a policy restricting AI companies from interacting with users on WhatsApp, a messaging platform owned by Meta. In a press release announcing the investigation, EU regulators stated that they are “concerned that such new policy may prevent third-party AI providers from offering their services through WhatsApp.”
  • Netflix (No. 116) won the bidding war for the studio and streaming businesses of Warner Bros. Discovery (No. 114) in a cash and stock deal worth roughly $72 billion. If approved by regulators, the acquisition would strengthen Netflix’s dominance in the media and entertainment industry. In a letter to Warner Bros. CEO David Zaslav earlier in the week, rival bidder Paramount (No. 147) accused Warner Bros. of favoring Netflix during negotiations, Bloomberg reported. Read more: Top analyst says Netflix’s $72 billion bet on Warner Bros. isn’t about the ‘Death of Hollywood’ at all. It’s really about Google
  • Micron Technology (No. 170) is discontinuing its Crucial consumer business to free up resources for its memory and storage business amid surging demand from data centers and artificial intelligence. The company also announced a $9.6 billion investment to expand its operations in Hiroshima, Japan with a new memory chip plant, per Nikkei Asia.
  • The U.S. Department of Justice approved a $16.4 billion deal for Constellation Energy (No. 186) to acquire Calpine, expanding the energy giant’s existing portfolio. Constellation Energy agreed to sell four power plants, and stakes in other facilities, as part of the approval process.
Overheard
“You didn’t have to teach a kid how to scroll, right?”
—Yulie Kwon Kim, VP of product at Google Workspace, sharing findings with Fortune from her organization’s new study that concluded many Gen Zers consider AI to be a native part of working
In interviews with Fortune 500 CEOs:
  • When Chris Boerner became CEO of Bristol-Myers Squibb (No. 94) two years ago, he arrived amid a looming “patent cliff,” with three key drugs (which accounted for almost half of the company’s revenue last year) close to losing exclusivity, and the loss of patent protection threatening to cost the company billions a year. But today, Boerner tells Fortune’s Diane Brady he’s optimistic about the pipeline of innovation, his team, and the opportunities to create a more equitable landscape for patients. “You have to have a great team of leaders,” Boerner says. “It’s also being able to inspire people and know how to manage the complexities that we face.” Read the full conversation