Defense leaders Steve Feinberg, the creator of Cerberus Capital Management, and Emil Michael, previously the No. 2 at Uber, were said to have been involved in a tense meeting at the Pentagon with Anthropic.
Defense leaders Steve Feinberg, the creator of Cerberus Capital Management, and Emil Michael, previously the No. 2 at Uber, were said to have been involved in a tense meeting at the Pentagon with Anthropic.
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The Pentagon’s private-sector A-Team
Earlier today, ahead of a meeting between Defense Secretary Pete Hegseth and Anthropic CEO Dario Amodei, my colleague Hayden Field and I released a report on the Pentagon’s aggressive contract renegotiations with Anthropic. The stakes are elevated beyond what seems reasonable, with the Pentagon still classifying Anthropic as a “supply-chain risk” unless the firm adheres to their conditions regarding their acceptable use policy.
In a meeting summary, Axios stated that Hegseth brought along several other high-ranking Defense officials to convey that the Pentagon was addressing the conflict “earnestly.” However, in a post-DOGE Trump administration led by oligarchs, it’s wise to examine the backgrounds of those attending. Some were regular senior officials who’d dedicated their careers to public service and military roles, but others held somewhat atypical histories:
- Pentagon CTO Emil Michael, who we’ve reported has been leading talks with Anthropic. Michael may ring a bell to longtime Verge readers and fans of Silicon Valley corporate drama as he was formerly the second-in-command at Uber during Travis Kalanick’s tenure as CEO. Michael exited in 2017 following an investigation that found he and several other top executives who dubbed themselves the “A-Team,” fostered a culture of sexual harassment within the company.
- For those inquisitive about his surveillance background: At a 2014 dinner with various journalists, Michael suggested that Uber employ opposition researchers to collect personal “dirt” on reporters writing negative stories, indicating his intent to target a female journalist who had recently criticized the firm for its misogynistic culture. This was also around the time Uber faced scrutiny for an internal tool named “God Mode,” used by employees to monitor user activity, including one BuzzFeed journalist covering an Uber executive.
- Deputy Secretary Steve Feinberg, the founder of the private equity firm Cerberus Capital Management, which manages approximately $65 billion in assets with a focus on “troubled properties.” Feinberg is widely blamed for the demise of Chrysler, and was an early supporter of Donald Trump, contributing to his 2016 presidential campaign and serving on the president’s intelligence advisory board in 2018. During his 2025 Senate confirmation hearing, Feinberg highlighted Cerberus’ investments in firms involved in national security, claiming he had “extensive experience with the Pentagon as a contractor and comprehend[s] its structure and operations.”
- At the time, Democrats expressed concerns that Feinberg might face conflicts of interest due to Cerberus’ investments in defense firms such as DynCorp. (During that year, DynCorp settled a lawsuit with the Department of Justice over allegations of “willfully inflating subcontractor charges under a State Department contract to train Iraqi police forces.”)
- In 2023, while Feinberg was still with Cerberus, the firm initiated Cerberus Ventures, a venture capital division focusing on investing in early-stage companies that tackle national security challenges in critical infrastructure.
- Hegseth’s chief spokesperson, Sean Parnell, an Army veteran who, in 2021, sought to compete for an open Senate seat in Pennsylvania. Despite winning Trump’s endorsement in the fiercely contested Republican primary, he had to withdraw in November after his ex-wife made serious allegations of physical and psychological abuse during a custody hearing, resulting in her being granted full legal custody. (Dr. Mehmet Oz, currently in the Trump administration, eventually clinched the nomination.)
The presence of Feinberg and Michael is noteworthy. Certainly, they possess some defense sector experience: Michael was a White House fellow during the Obama administration and served two years as a special assistant to Defense Secretary Robert Gates at the Pentagon, which is significant. Feinberg has undoubtedly spent time involved with defense contracts. Yet, one must recognize the aggressive business mentality that private sector individuals tend to introduce into government — especially regarding high-stakes negotiations like these. Parnell’s involvement makes sense in the scope of “acting as Hegseth’s spokesperson.”
The single-supplier shuffle
One subject Hayden and I did not have the opportunity to delve into further was the “single-supplier vulnerability” debate, but it has become a pivotal element in negotiations.
In 2024, the Biden administration issued a national security memorandum pertaining to the use of artificial intelligence, which outlined several directives about safeguarding the supply chain. Among these was a directive mandating the Department of Defense to uphold contracts with at least two leading AI labs authorized to handle classified information, in order to avert a situation where one compromised vendor could jeopardize an entire IT infrastructure. As early as summer 2025, it’s understood that the Trump administration was addressing that vulnerability. Though they had signed distinct contracts with Anthropic, Google, xAI, and OpenAI, only the Anthropic model was approved for classified use when Hegseth distributed his memo specifying the new AI guidelines in January.
This conundrum has left the Pentagon in a precarious position: Even if they manage to exclude Anthropic and navigate the complex process of requiring all defense contractors to remove Claude from their operations, they run the risk of falling short of the Department’s own specifications, not to mention basic logic. (Avoiding single-supplier vulnerability is a fundamental practice in the tech field.)
This indeed adds more context to the Pentagon’s decision last night to swiftly provide xAI’s Grok access to classified systems, despite Grok being widely regarded as the least capable among the available models. While The New York Times reported that Google is nearing a deal that would allow the Pentagon to utilize Gemini for classified operations, defense insiders view Gemini as a quality competitor to Claude, whereas xAi’s Grok “is not considered as advanced or reliable as Anthropic’s.” OpenAI is not close to finalizing a deal, as the company has indicated it must enhance ChatGPT’s safety protocols prior to deploying it within classified networks.
Thus, let’s assess the situation. With four AI models at your disposal, you need to collaborate with two of them. Your options are:
1) A company offering a decent AI model and increasingly flexible ethics
2) A company with the top AI model, yet unwilling to allow its use for autonomous lethal actions without human oversight
3) A company whose AI model remains insecure for deployment
4) A company using AI that has racist biases and creates inappropriate content, and which you do not regard as “advanced or reliable”
If you cannot engage with companies 2 and 3, you are left with companies 1 and 4, which even defense officials acknowledge is not ideal from a national security standpoint. “The only reason we’re still in communication with these folks [Anthropic] is due to our necessity for them, and we need them urgently. The challenge for these guys is their competency,” a Defense official conveyed to Axios prior to the meeting.
Loomering the dip
The recent negotiations of the Clarity Act between the finance and crypto sectors last week accidentally morphed into the latest installment of the recurring theme I am now referring to as: “Why is Laura Loomer tweeting about niche tech topics as if they are tests of loyalty to MAGA?”
Last Thursday, a small assembly of influential crypto and finance figures gathered at the White House to further negotiate draft language regarding stablecoin yields. Coinbase, which initiated these discussions after withdrawing support from Clarity over stablecoin yields, was present. However, prior to the meeting, Loomer sent out a classic tweet showcasing her strategies for exerting influence over Trump: Portray the target as someone who previously aligned with Trump’s adversaries and thus is disloyal.
Ironically, Coinbase has evolved into one of the largest overt supporters of the Trump administration, contributing to his favored initiatives and even having their branding prominently displayed in last year’s military parade.
Although Loomer expressed a similar opinion about Coinbase last June, it appears to have not affected Coinbase’s access to Trump, and likely won’t for the foreseeable future: I have been informed that CEO Brian Armstrong was at Mar-a-Lago the day before Loomer tweeted, attending a World Liberty Financial event.
A wild Trumpworld character has appeared!
If you have been following the story of Logan Paul selling his Pokémon card collection, you may know that one of those cards was sold for a staggering $16.5 million last week. But who was the buyer of that Pokémon? It’s AJ Scaramucci, the son of the notable Anthony Scaramucci, the New York financier and former Trump associate who notoriously served as Trump’s White House Communications Director for 10 days in 2017.
AJ is the founder of Solari Capital, which invested $100 million into a Bitcoin mining operation managed by Eric Trump. He has also acquired the Pikachu Illustrator card, one of merely 39 cards that exist and in Grade 10 condition, along with the diamond necklace and case that Paul wore to showcase the card during his appearance at WrestleMania 38. Scaramucci indicated to reporters that he bought the card as part of his forthcoming “global treasure hunt,” adding that he also aimed to acquire a T. rex skull and the Declaration of Independence. (He later shared on X that he hopes to display the card in the Nintendo Museum in Kyoto and establish it as “the ‘Mona Lisa’ of the Pokemon collection.”)
And now, Recess.
It’s hard to believe a court had to spell this out for you, let alone the Southern District of New York: If you input correspondence between you and your attorney into a public AI platform, it loses its attorney-client privilege and becomes subject to discovery!!!!
In any event, enjoy your State of the Union viewing party (if that’s still a thing) and we’ll see you next week.
