Emil Michael, the primary Pentagon official responsible for overseeing military artificial intelligence policy, has sold his stake in the AI search engine company Perplexity, The Guardian reported. Financial records indicate the sale occurred in June and was valued between $5m and $25m. Because federal financial disclosures provide broad dollar ranges rather than exact figures, it remains unclear whether he made a profit on this specific transaction. This divestment follows a series of high-value financial moves by Michael during his time in federal service. Earlier this year, disclosures revealed he profited from his investment in Elon Musk’s xAI, seeing gains between 400% and 4,800% after selling his holdings in January. These transactions have sparked a conversation about the intersection of personal wealth and government oversight in the fast-moving AI sector. Michael’s relationship with Perplexity appears multifaceted based on his 2025 financial disclosures. He previously received a personal loan from the company of between $250,000 and $500,000 at a 4.57% interest rate. Furthermore, he held a position on a Perplexity advisory board, though his filings state he resigned from that role upon beginning his government position. The Pentagon has defended the activities of its officials Perplexity secured a contract with the General Services Administration in November of last year, although there are no records linking the company directly to the Pentagon. Regarding his stock, some shares were vested while others were unvested, and he pledged in his ethics agreement to avoid profiting from the unvested portion. JUST INThe Pentagon's top official for military AI just sold another company's stock for up to $25 million.He oversees AI policy for the US military. Here's what he's been selling: pic.twitter.com/jHJQiFxrap— Insiderwave (@insiderwave) September 1, 2026 A spokesperson stated that Michael and other defense personnel are “in full compliance with ethics laws and regulations. Any claims otherwise are false.” The department emphasized that it maintains a rigorous, multi-layered ethics framework. However, not everyone agrees that these actions meet the standard of public service. Richard Painter, a former White House lawyer under President George W Bush, argued that Michael should have divested his interests before entering his current role. He noted that while holding the stock might not technically violate the law, it creates a difficult appearance for a government official. According to Painter, most administrations would have insisted that an official liquidate such assets before starting a job that directly impacts the industry. Michael’s financial activity extends beyond AI-focused companies. In April, he sold his stake in Brex LLC, a financial software firm, for at least $5m. This move yielded significant gains, as he had reported his Brex holdings were worth a maximum of $750,000 in March 2025. The profit from this sale could range from $4.25m to $24m. Michael previously served as a consultant for the firm, which was acquired by Capital One in April. While Brex does not appear to have direct government contracts, Michael’s public-facing role at the Pentagon has placed him in the spotlight, specifically as the face of the department’s work regarding the AI company Anthropic. Beyond his policy work, Michael has maintained a public profile as a guest on various podcasts. He appeared on a program in December titled “Misunderstood Power: Emil Michael on the Truth about DOW and Defense Tech,” which was sponsored by Brex while he was still an investor. Michael, who served as the chief business officer at Uber from 2014 to 2017, has a history of public scrutiny. In 2014, reports surfaced that he had discussed investigating journalists who were critical of his former employer, though he later stated those comments did not reflect his actual views.