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Situational Awareness retains Anthropic stake despite public portfolio sell-off

Ex-OpenAI researcher Leopold Aschenbrenner's hedge fund faces losses but keeps key private investments.

16 August 2026 · 5 min read

Situational Awareness retains Anthropic stake despite public portfolio sell-off

Situational Awareness, a hedge fund founded by former OpenAI researcher Leopold Aschenbrenner, has made headlines recently following its sale of the majority of its public stock portfolio. This strategic shift comes amid considerable losses in the hedge fund’s technology/">investments. However, it appears that Aschenbrenner is still holding onto some valuable private stakes, including a significant investment in the AI company Anthropic.

The rise and fall of a hedge fund star

Aschenbrenner launched Situational Awareness in 2024, quickly gaining attention with his ambitious investment strategy that focused on the burgeoning AI sector. The 25-year-old German-born former valedictorian of Columbia University found initial success thanks to his innovative approach to AI infrastructure. His early thesis asserted that scaling AI technology would require extensive investment in critical areas such as semiconductors, computing power, memory, and energy resources.

Before founding the fund, Aschenbrenner was part of OpenAI’s “superalignment” team, where he was recognized for his intelligence and vision. However, his tenure at OpenAI was short-lived; he was dismissed due to issues related to improper disclosures of internal information. Following this, he pivoted, establishing Situational Awareness and drawing significant backing from notable investors and firms.

As reported by the Financial Times, the fund had an explosive return of 439% through June 2023, with assets peaking at approximately $45 billion. This meteoric rise, however, was quickly eclipsed by a substantial decline in the value of AI infrastructure stocks. The valuation woes of the tech sector contributed directly to the hedge fund's struggles, compelling it to unwind many of its public equity stakes.

The impact of market dynamics

According to sources, such as a recent report by the Wall Street Journal, Situational Awareness suffered from significant losses due to several factors. The fund’s leveraged investments—a common strategy in hedge funds—amplified the impact of the downturn. Stocks in which Situational Awareness had invested, including renowned companies such as SK Hynix and Sandisk, saw declines exceeding 30%. This drop prompted Aschenbrenner to take decisive action.

In July, he reached out to investors with a letter that characterized the sell-off as an ideal buying opportunity. Despite his optimistic message aimed at urging clients to inject fresh capital into the fund starting August 1, the response was lukewarm, and the hoped-for influx failed to materialize.

Citadel's involvement in the sell-off

As Situational Awareness unwound its public investments, Citadel, led by Ken Griffin, emerged as a key player in acquiring these assets. Citadel is known for capitalizing on distressed sales and swooping in to purchase quality assets when other hedge funds are forced to divest. Following Citadel's acquisition of most of Situational Awareness’s public equity positions, the fund’s overall assets reportedly decreased to around $10 billion.

Despite the struggles faced by the fund’s public investments, it has maintained its position within various private ventures, most notably its stake in Anthropic. Reports indicate that the hedge fund’s investment in Anthropic is valued around $5 billion, a substantial asset considering the growth trajectory of this AI company. Anthropic was recently valued as high as $965 billion during its latest funding round, and forecasts suggest it could go public imminently, potentially at an even higher valuation.

Future outlook for Situational Awareness

The retention of private investments seems strategic, particularly as Aschenbrenner's exposure to the more volatile public markets diminishes. His ongoing stake in Anthropic symbolizes a commitment to the core tenets of his investment thesis, emphasizing the transformative potential of AI technologies.

Additionally, Situational Awareness's portfolio still includes promising firms within the AI ecosystem, such as MatX, a chipmaker, and Fluidstack, an AI data center startup. Fluidstack, in particular, is reported to have been discussing new funding at a staggering $18 billion valuation earlier this year.

As Aschenbrenner navigates through this tumultuous period, the outcome of his decisions remains to be seen. His adeptness at recognizing and managing potential risks will be crucial as he determines how best to leverage Situational Awareness's remaining assets. While the losses experienced in the public markets represent a serious challenge, the sustained growth of investments in private companies may yet provide the cushion needed to support Situational Awareness through its current crisis.

Looking ahead

Leopold Aschenbrenner’s journey reflects the volatile nature of hedge funds in today’s market landscape. Although the recent sell-off has posed considerable challenges, his focus on retaining the hedge fund’s private investments could prove to be a wise long-term strategy as the AI sector continues to evolve. With a potential initial public offering for Anthropic looming on the horizon, there is a possibility that the hedge fund could recover its footing rapidly, particularly if it capitalizes on its remaining key assets effectively.

The road ahead for Situational Awareness is undoubtedly fraught with challenges, but Aschenbrenner’s skillset, combined with the value of the private investments held, may position the fund for future success in the AI-driven investment landscape.

Frequently asked questions

What is Situational Awareness hedge fund?

Situational Awareness is a hedge fund founded by ex-OpenAI researcher Leopold Aschenbrenner, primarily focused on investing in AI technologies and related infrastructure.

Why did Situational Awareness sell its public portfolio?

The hedge fund faced significant losses in its public investments due to a decline in AI infrastructure stocks and leveraged trading strategies, prompting it to divest from public equities.

What private investments does Situational Awareness hold?

The hedge fund retains key stakes in private companies, including a substantial investment in Anthropic, valued at approximately $5 billion, along with interests in other technology firms such as MatX and Fluidstack.