A 24-year-old former OpenAI researcher just became Wall Street’s most expensive cautionary tale. Leopold Aschenbrenner’s Situational Awareness LP hedge fund sold its entire public equity portfolio, roughly $16 billion worth of AI stocks, to Citadel in a single block trade this month after its leveraged bets cratered.
From moonshot to meltdown
Situational Awareness launched in late 2024 with approximately $225 million in initial capital. By the end of June 2026, the fund had posted net returns of roughly 439% year-to-date, ballooning its assets under management north of $20 billion.
The fund was running leverage of nearly four times its equity base. Key AI positions in the portfolio fell 40-50% during the recent period before the unwind.
The portfolio included AI infrastructure plays: Bloom Energy, Nebius (formerly SanDisk), CoreWeave, IREN, and Core Scientific. The book also included Bitcoin miners who had pivoted to data center operations: Riot, CleanSpark, HIVE, and Bitdeer.
