Situational Awareness Tipped Its Hand Shopping Anthropic Stake

On the afternoon of Wednesday, July 29, a broker rang David Mann to ask if he wanted a slice of Situational Awareness's Anthropic stake, with a deal that had to close by morning. As The Wall Street Journal reported, Mann was in a taxi to LaGuardia when the call came, and "Wall Street's AI wunderkind was in trouble." Pre-IPO paper in a company valued near $1 trillion does not move overnight unless the seller is on the ropes.

Leopold Aschenbrenner's AI-focused fund, launched in 2024 at age 23 with no prior trading experience, had returned 439% through June and swelled toward $45 billion at its peak. July undid a large piece of it. Concentrated AI holdings plummeted more than 30% over the month, and the fund shed 67% of its value before selling the bulk of its public book to Ken Griffin's Citadel. Assets landed at roughly $10 billion, down from around $20 billion in recent months, TechCrunch reported, citing Bloomberg on the roughly $5 billion Anthropic position that came out the other side intact.

Aschenbrenner told investors the dynamic looked like a bank run, each sign of vulnerability creating more vulnerability. The fund said rapidly falling positions and fading market liquidity made the portfolio harder to keep inside its risk limits. Five days earlier, a July 24 letter had called the selloff "one of the best buying opportunities since early last year."

The exact haircut Citadel paid is not in the public reporting, and neither is a per-name breakdown of the July losses or the price attached to the Anthropic slice shopped overnight. What is public is the tell itself. Once counterparties saw pre-IPO Anthropic shares moving on an overnight timeline, the fund's leveraged public book stopped trading as an ordinary drawdown and started trading as a forced seller. Anthropic private-market activity now sits at the center of that read, and it is one of the more heavily tracked names in our coverage.