Situational Awareness retains its prized Anthropic stake as Citadel swoops in to buy distressed AI portfolio

Leopold Aschenbrenner's AI-focused hedge fund Situational Awareness sold the majority of its leveraged public equity holdings to Ken Griffin's Citadel in a deal that closed around July 30, 2026, while retaining its prized stake in Anthropic, which accounts for about 20% of the fund's $20 billion in assets. The fund's Anthropic position, first invested when the company was valued at roughly $60 billion in February 2025, has surged to approximately $965 billion by May 2026, driving reported returns of around 270% after fees, though those gains remain largely unrealized paper profits on a private company.

Via penlink.com Situational Awareness retains its prized Anthropic stake as Citadel swoops in to buy distressed AI portfolio Leopold Aschenbrenner's AI-focused hedge fund offloaded leveraged public equity positions to Ken Griffin's firm while holding onto its most valuable private bet Leopold Aschenbrenner’s hedge fund Situational Awareness just did the financial equivalent of selling the furniture to keep the house. The AI-centric fund unloaded the majority of its leveraged public equity holdings to Citadel, Ken Griffin’s trading powerhouse, in a deal that closed on or around July 30, 2026. The fund kept its crown jewel: a significant stake in Anthropic, the AI safety company whose valuation has ballooned to roughly $965 billion. That position alone accounts for approximately 20% of the fund’s total assets, or about $4 billion. What happened and why it matters Situational Awareness manages approximately $20 billion in assets. The fund had built up substantial leveraged positions in publicly traded AI stocks, a strategy that works beautifully on the way up and rather less beautifully on the way down. Citadel stepped in after what’s described as a brief bidding process. The deal allowed Situational Awareness to shed its most vulnerable positions, the leveraged public equity holdings, while retaining two categories of assets: its unlevered client-funded public positions and its private investments. The Anthropic position is the big one. Situational Awareness first invested when Anthropic was valued at approximately $60 to $61.5 billion back in February 2025. By May 2026, that valuation had surged to around $965 billion. That’s roughly a 15x appreciation in just over a year, which helps explain why the fund has reported returns of around 270% after fees through May 2026. Here’s the thing: those returns are almost entirely a paper gain on a private company. You can’t sell a chunk of Anthropic on a Tuesday afternoon the way you can dump Tesla shares. The illiquidity of that position is both its greatest strength no daily mark-to-market panic and its greatest vulnerability good luck raising cash from it quickly . The leverage problem in AI investing Aschenbrenner, who previously worked at OpenAI before departing under contentious circumstances, built Situational Awareness around the thesis that artificial intelligence would transform the global economy faster than most people anticipated. Leveraged positions amplify gains on the way up and losses on the way down. When AI stocks pulled back broadly, the fund’s borrowed-money bets started generating margin pressure. Rather than face a forced liquidation at distressed prices, the fund chose to sell proactively to Citadel, which has the balance sheet and risk appetite to absorb a large portfolio of discounted AI equities. What this means for investors The gap between private market valuations where Anthropic sits near $965 billion and public market sentiment where leveraged AI stock positions are blowing up is telling. One notable detail from this entire saga: no cryptocurrencies or digital assets were involved in the transaction or reported anywhere in the fund’s holdings. For a fund managing $20 billion with a technology-forward thesis, the complete absence of crypto exposure is a deliberate choice. The risk to watch now is concentration. Situational Awareness has shed its diversified public equity portfolio and is left holding a more concentrated book anchored by a single massive private position in Anthropic. If Anthropic’s valuation compresses, or if the company faces competitive headwinds from OpenAI, Google DeepMind, or emerging Chinese labs, the fund’s 270% return could erode significantly before it ever crystallizes into actual realized gains. Disclosure: This article was edited by Editorial Team. For more information on how we create and review content, see our Editorial Policy https://cryptobriefing.com/editorial-policy/ .