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Pete Hegseth’s Pentagon AI bro squad includes a former Uber executive and a private equity billionaire

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The Pentagon’s private-sector A-Team

This morning, in advance of a meeting between Defense Secretary Pete Hegseth and Anthropic CEO Dario Amodei, my colleague Hayden Field and I published a story about the Pentagon’s hardball contract renegotiations with Anthropic. The stakes are higher than it should reasonably be, with the Pentagon continuing to designate Anthropic a “supply-chain risk” if the company doesn’t comply with their demands about their acceptable use policy.

In a post-meeting readout, Axios reported that Hegseth brought several other senior Defense officials to the meeting in an attempt to show that the Pentagon was taking the dispute “seriously.” But in a post-DOGE Trump administration run by broligarchs, it’s always worthwhile to check the attendees’ bios. Some of them were normal senior officials who’d spent their careers in government and military work, but the others have somewhat unusual backgrounds:

Feinberg and Michael’s presence should draw eyeballs. Yes, they both have some amount of defense industry experience: Michael was a White House fellow during the Obama administration, and spent two years as a special assistant to Defense Secretary Robert Gates at the Pentagon, which isn’t nothing. Feinberg has clearly spent time with defense contracts. But one must fully appreciate the rapacious business mindset that private sector types love to bring into the government — especially with high-stakes negotiations such as this. Parnell’s presence, meanwhile, makes sense within the context of “being the spokesman for Pete Hegseth.”

The single-supplier shuffle

One topic Hayden and I didn’t get to explore more was the “single-supplier vulnerability” issue, but it’s turning into a crucial factor in negotiations.

In 2024, the Biden administration released a national security memorandum on the use of artificial intelligence, which laid out several directives regarding the protection of the supply chain. Among them was a directive for the Department of Defense to maintain contracts with at least two frontier AI labs that were cleared to handle classified information, in order to prevent a scenario where one compromised vendor could take down an entire IT system. But as early as the summer of 2025, I’m told, the Trump administration was trying to address that vulnerability. While they had signed separate contracts with Anthropic, Google, xAI, and OpenAI, only Anthropic’s model was cleared for classified use when Hegseth published his memo outlining his new AI policy in January.

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