Leopold Aschenbrenner is back to losing money in AI stocks

Leopold Aschenbrenner of hedge fund Situational Awareness has returned after losing billions of dollars in July — and he’s already losing money again. 

CNBC broke the news Friday morning, six weeks after Aschenbrenner’s historic blow-up, that Situational Awareness was re-buying AI stocks and leveraged options on tech stocks.

By Monday’s open, every one of the six tickers tied to his fund had already collapsed, down as much as 8% from Friday’s close.

Situational Awareness is the fund Aschenbrenner still runs after a July collapse in AI valuations erased billions of assets from his portfolio. 

Despite one of the most spectacular and well-publicized implosions of any fund manager in history, Situational Awareness quietly bought options tied to AMD, Bloom Energy, and CoreWeave this month. It also bought leveraged exposure to other AI names like SK Hynix, SanDisk, and the Roundhill Memory ETF. 

CNBC sources dated those purchases between September 2-10. 

The day after that news broke, those six names opened to negative returns of 5-8% amid a broad AI sell-off this morning.

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Leopold Aschenbrenner is losing money in AI again

Those six tickers didn’t fall because of Aschenbrenner but rather a viral, apocalyptic essay from Anthropic CEO Dario Amodei who believes that AI will take over the internet within 6-12 months.

Elon Musk said he agreed with it, and Sam Altman also backed the idea. 

Broad Monday market coverage framed the resulting sell-off as a rotation out of crowded AI trades. Even Donald Trump weighed in on the debate.

The world found out Aschenbrenner was re-buying Friday, and all of his stocks were down by Monday.

• AMD closed for trading at $516.13 the day CNBC’s story ran; it opened Monday around $486, down roughly 6%. 
• Bloom Energy fell 7%.
• CoreWeave and SanDisk each fell roughly 7%.
• SK Hynix and the Roundhill Memory ETF each fell about 8%.

Aschenbrenner, a former OpenAI researcher, launched Situational Awareness in 2024 with about $225 million.

Backers included Stripe co-founders Patrick and John Collison, former GitHub chief exec Nat Friedman, and investor Daniel Gross. 

Using leverage as high as 400%, Aschenbrenner grew his portfolio and attracted follow-on financing to manage more than $45 billion by the start of July. 

Then he suddenly lost the majority within weeks. 

In July, AI stocks retraced a substantial amount of the price appreciation they had enjoyed during the first half of 2026. 

Shares of Nebius, SanDisk, Micron, and CoreWeave each fell by more than one-third that month, forcing margin calls and an unwind across tech funds. 

Liquidated in a fire sale, moved prime brokers

Ken Griffin’s Citadel bought the bulk of Situational Awareness’ portfolio at a substantial discount — reportedly after its holdings had sunk to roughly $10 billion, in what the Financial Times called the largest dollar loss in hedge fund history. 

JPMorgan Chase, which had financed the fund’s leverage, cut the fund off afterward. Aschenbrenner moved his prime brokerage relationship to another boutique, Clear Street.

The comeback trade this month was supposed to look different. Rather than traditional margin, the fund has reportedly been using “flex options,” i.e. fully paid contracts that cap losses at the premium paid. 

The shift in those instruments is tied to Aschenbrenner’s promise of a more conservative risk model that doesn’t seem to be particularly well-timed, given this weekend’s sell-off, regardless of its leverage ratio.

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