Emil Michael, the top Pentagon official overseeing military artificial intelligence policy, sold his holdings in AI-powered search engine company Perplexity in June 2026 for between $5 million and $25 million, according to federal financial records seen by the Guardian. ^[1] Emil Michael, the Pentagon's undersecretary of defense for research and engineering and chief technology officer, sold his stake in Perplexity AI in June 2026 for between $5 million and $25 million, according to financial disclosures reviewed by The Guardian. ^[2] U.S. District Judge Rita Lin ruled in 2026 that the Pentagon's blacklist of Anthropic illegally retaliated against the company for refusing to let its models be used for mass surveillance and autonomous lethal operations, vacating the designation and issuing a permanent injunction. ^[3] Ethics expert Richard Painter, a former White House lawyer under George W. Bush, said Michael should have sold all interest in Perplexity before starting his job, and that most administrations would have required that. ^[4] In January 2026, Emil Michael sold his private investment in Elon Musk's AI company xAI, reaping gains of between 400% and 4,800% and profits of up to $24 million, according to federal financial disclosures previously reported by the Guardian. ^[5] Michael received a personal loan from Perplexity in 2024 of between $250,000 and $500,000 at a 4.57% interest rate, and joined the company's advisory board, from which he stepped down when entering federal service, according to his financial disclosure filings. ^[6] Michael also sold his stake in Elon Musk's xAI on 2026-01-09 for between $5 million and $25 million, a gain of up to 4,800% compared with the $500,000 to $1 million value reported when he entered government, according to IBTimes UK. ^[7] U.S. President Donald Trump ordered federal agencies to stop using Anthropic's technology on 2026-02-27, and the Pentagon subsequently branded the company a 'supply chain risk', barring military contractors from doing business with it. ^[8]