Emil Michael, the Pentagon’s undersecretary of defense for research and engineering and chief technology officer, sold his Perplexity AI stake in June for between $5 million and $25 million, according to financial disclosures reviewed by The Guardian. The sale was his third AI-adjacent exit this year, following a reported gain of up to $24 million on xAI in January and at least $5 million from a Brex stake in April. Michael previously served on Perplexity’s advisory board and left at the start of 2025 before joining the Donald Trump administration in May. His disclosures also show a prior personal loan from Perplexity worth between $250,000 and $500,000 at 4.57% interest. The transactions have drawn scrutiny because Michael became the public face of the Pentagon’s campaign against Anthropic, a rival to Perplexity and xAI, while the department awarded classified-network work to competing AI companies. A federal judge later vacated Anthropic’s designation as a supply chain risk, ruling that it unlawfully retaliated against the company.