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Pentagon AI Official Sold Millions in Perplexity Stock

Created at 2 Sep · 8:51 PM1 source↑ Market-relevant
IN SHORT

Emil Michael, the Pentagon's undersecretary of defense for research and engineering, sold his Perplexity AI stake in June for between $5 million and $25 million. This marks his third AI-adjacent stock exit this year, following gains on xAI and Brex.

Key Numbers

$5 million to $25 millionPerplexity AI stake sale value
$5 million to $25 millionxAI stake sale value
4,800%xAI stake sale gain
$250,000 to $500,000Perplexity personal loan amount
4.57%Perplexity loan interest rate
$20 billionPerplexity valuation in September 2025
50%Perplexity valuation increase
$30 billionPerplexity's potential new valuation

Who's Involved

Emil Michael
Pentagon's undersecretary of defense for research and engineering
Perplexity AI
AI company whose stock was sold by Emil Michael
xAI
AI company whose stock was sold by Emil Michael
Brex
Company whose stock was sold by Emil Michael
Anthropic
AI company blacklisted by the Pentagon
Rita Lin
U.S. District Judge who ruled on Anthropic's designation
Richard Painter
Former White House ethics lawyer
Donald Trump
President who ordered federal agencies to stop using Anthropic's technology
Pentagon AI Official Sold Millions in Perplexity Stock

↳ Why This Matters

The sales raise questions about potential conflicts of interest for a high-ranking Pentagon official involved in AI procurement and policy, particularly concerning companies that compete for government contracts.

Key facts

  • Emil Michael, Pentagon undersecretary of defense for research and engineering, sold his Perplexity AI stake in June.
  • The sale generated between $5 million and $25 million.
  • This is Michael's third AI-related stock sale this year, following exits from xAI and Brex.
  • Michael previously served on Perplexity's advisory board.
  • The Pentagon had previously blacklisted Anthropic, a competitor to Perplexity and xAI, but a judge vacated the designation.

Emil Michael, the Pentagon's undersecretary of defense for research and engineering, sold his stake in Perplexity AI in June for between $5 million and $25 million, according to financial disclosures. This marks his third significant AI-adjacent stock exit this year, following a substantial gain on his xAI stake and a sale of Brex stock.

Michael previously sat on Perplexity's advisory board and stepped down before joining the Trump administration. His disclosures reveal he also held a stake in Elon Musk's xAI, which he sold in January for between $5 million and $25 million, representing a gain of up to 4,800%. The timing of the xAI sale occurred shortly after the Pentagon signed a new agreement to deploy xAI's Grok on its classified networks, despite Michael receiving a divestiture certificate for the holdings days earlier.

Before entering government service, Michael received a personal loan from Perplexity. Ethics specialists have raised concerns about the timing of these sales. Richard Painter, a former White House ethics lawyer, stated that Michael should have divested his interests before joining the government. A Pentagon spokesperson, however, asserted that Michael and other defense officials are in full compliance with ethics laws and regulations.

The disclosures come as Michael has been a prominent figure in the Pentagon's efforts to blacklist Anthropic, a competitor to Perplexity and xAI. The Pentagon had barred military contractors from doing business with Anthropic, citing it as a 'supply chain risk.' However, a federal judge recently vacated this designation, ruling it was an illegal retaliation. OpenAI has since taken over a Pentagon contract that was initially intended for Anthropic.

Frequently asked questions

Emil Michael is the Pentagon's undersecretary of defense for research and engineering and its chief technology officer.

Emil Michael has sold stakes in Perplexity AI, xAI, and Brex this year.

The Pentagon blacklisted Anthropic, a competitor to Perplexity and xAI, but a federal judge vacated the designation, ruling it was illegal retaliation.

Perplexity AI is in talks for a funding round that would value it above $30 billion, up from $20 billion in September 2025.

What Happens Next

01Perplexity AI is reportedly in talks with Nvidia for a new funding round.
02The Pentagon continues to sign classified-network deals with other AI companies.

How It Developed

Emil Michael sold his Perplexity AI stake in June for $5 million to $25 million.
Michael previously sat on Perplexity's advisory board.
He sold a stake in xAI in January for $5 million to $25 million.
The Pentagon signed a deal to deploy xAI's Grok on classified networks days after Michael received a divestiture certificate for xAI holdings.
Michael took a personal loan from Perplexity before joining the government.
Michael has been involved in the Pentagon's efforts to blacklist Anthropic.
A federal judge vacated the Pentagon's designation of Anthropic as a supply chain risk.
OpenAI took over a Pentagon contract previously intended for Anthropic.

Sources

T1
Top Pentagon AI Official Sold Millions in Perplexity Stock, Disclosures ShowDecrypt

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