Situational Awareness holds $5B stake in Anthropic, signaling where smart money is actually flowing

Leopold Aschenbrenner’s hedge fund, Situational Awareness LP, holds a $5 billion stake in Anthropic, according to a report from the Financial Times. The position represents roughly one-fifth of the fund’s total assets under management, which have ballooned to approximately $20 billion since launch. From OpenAI exile to billion-dollar bets Aschenbrenner departed OpenAI in April 2024 and promptly did what any self-respecting AI researcher would do: wrote a pivotal essay about AI’s trajectory, then started a hedge fund to put his money where his thesis was. The fund’s strategy has been unapologetically concentrated. Rather than spreading bets across the AI landscape, Situational Awareness LP went heavy on Anthropic, the Claude-maker founded by former OpenAI researchers Dario and Daniela Amodei. The Anthropic stake was initially acquired when the company was valued at around $60 billion back in February 2025. The company’s Series H funding round, which closed on May 28, 2026, raised $65 billion and pegged Anthropic’s post-money valuation at $965 billion. Returns that read like a typo The fund has reportedly generated approximately 270% net returns after fees as of May 2026. Since incep...