Pentagon’s AI Showdown: The Broligarchs, The Scandals, and The $16 Million Pokémon Card

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The Pentagon’s Private-Sector A-Team

This morning, ahead of a high-stakes meeting between Defense Secretary Pete Hegseth and Anthropic CEO Dario Amodei, we broke the story on the Pentagon’s hardball contract renegotiations with Anthropic. The stakes? Sky-high. The Pentagon is threatening to label Anthropic a “supply-chain risk” unless they bend to demands about their acceptable use policy.

Axios reported that Hegseth brought senior Defense officials to the meeting to signal seriousness. But in Trump’s broligarch-run administration, it’s worth checking who’s in the room:

• Emil Michael (Pentagon CTO): Former Uber exec and Travis Kalanick’s “A-Team” member, ousted in 2017 after a sexual harassment scandal. He once suggested Uber hire “dirt” researchers to target female journalists and was linked to Uber’s “God Mode” surveillance tool.

• Steve Feinberg (Deputy Secretary): Founder of Cerberus Capital, the firm blamed for Chrysler’s collapse. A Trump donor and defense contractor with billions in assets, Feinberg’s Senate confirmation raised red flags over conflicts of interest with Cerberus’ defense investments.

• Sean Parnell (Hegseth’s chief spokesperson): Army veteran and failed Pennsylvania Senate candidate who dropped out in 2021 after his ex-wife alleged severe abuse, winning full custody.

Michael and Feinberg’s presence raises eyebrows—private-sector dealmakers in a government negotiation? Classic broligarch energy.

The Single-Supplier Shuffle

We didn’t dive deep into the “single-supplier vulnerability” issue, but it’s now central to the negotiations.

In 2024, the Biden administration mandated the DoD work with at least two AI labs cleared for classified work to avoid supply-chain risks. But by 2025, the Trump administration scrambled to fix this: Anthropic was the only model cleared when Hegseth unveiled his AI policy in January.

Now the Pentagon faces a dilemma: Cut Anthropic, and they risk non-compliance with their own rules. Even worse, they’d have to force defense contractors to remove Claude from workflows—an arduous process.

So last night, the Pentagon suddenly granted xAI’s Grok access to classified systems, despite it being the least capable model. Meanwhile, Google’s Gemini is close to a deal, but OpenAI won’t deploy ChatGPT on classified networks until safety features improve.

The math is brutal:

1. A company with a good model and flexible morals.
2. The best model, but it won’t let you kill autonomously.
3. A model not secure enough yet.
4. A racist, child-porn-generating model deemed “not advanced or reliable.”

If you can’t work with 2 and 3, you’re stuck with 1 and 4—not optimal for national security. As one official told Axios: “The only reason we’re still talking to these people is we need them and we need them now.”

The Crypto-Influencer Crossover

Last week’s Clarity Act negotiations turned into another episode of “Why is Laura Loomer tweeting about obscure tech as a MAGA loyalty test?”

Coinbase CEO Brian Armstrong was at Mar-a-Lago the day before Loomer’s tweet, attending a World Liberty Financial event. Coinbase, now a Trump booster, donated to his initiatives and even had its logo on last year’s military parade. Loomer’s rants? They barely dent Coinbase’s access.

A Wild Trumpworld Character Has Appeared!

Remember Logan Paul auctioning his Pokémon cards? One sold for a record $16.5 million—bought by AJ Scaramucci, son of Anthony Scaramucci (the “Mooch”). AJ, founder of Solari Capital, invested $100 million in Eric Trump’s Bitcoin mining platform and now owns the Pikachu Illustrator card, one of only 39 in existence.

He’s on a “planetary treasure hunt,” eyeing a T. rex skull and the Declaration of Independence. He plans to display the card in the Nintendo Museum in Kyoto as the “Mona Lisa of Pokémon.”

A Public Service Announcement

We can’t believe a court has to tell you this, much less the Southern District of New York: If you put lawyer-client correspondence into a public AI platform, it’s no longer privileged and can be discovered in court.

Have a great State of the Union watch party (if anyone still does that) and see you next week.

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• Laura Loomer MAGA loyalty tests
• Coinbase Trump booster
• $16.5 million Pokémon card
• AJ Scaramucci planetary treasure hunt
• Single-supplier vulnerability
• Grok classified access
• Attorney-client privilege AI disaster
• State of the Union watch party

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