The investment fund once dubbed the "AI stock guru" is staging a comeback, just one month after experiencing one of the largest single-fund losses in hedge fund history. Situational Awareness fund founder Leopold Aschenbrenner has begun rebuilding substantial trading positions in technology stocks including AMD, Intel, SK Hynix, SanDisk, and AI startup CoreWeave, according to people familiar with the matter.

After his previous brokerage relationships were almost entirely severed, Aschenbrenner has turned to Clear Street, a lesser-known specialist broker focused on the technology sector within hedge fund circles. The move has captured significant market attention because his trading approach closely mirrors the aggressive strategy that triggered massive losses in July. Strategists at Nomura have detected unusual market signals, noting a series of large flexible call option trades concentrated in multiple AI and semiconductor-related stocks last Friday and Tuesday following the Labor Day holiday, with total option premiums reaching $315 million. The linked pattern of rising spot prices accompanied by rising volatility closely resembles market characteristics observed before the July downturn.

The newly established positions are being executed through flexible options using fully-paid structures, covering the same core holdings that previously caused the fund's collapse. Detailed option activity reported from the Nomura trading desk showed substantial AMD call options purchased across two trading sessions, while clean energy company Bloom Energy saw option premium expenditures of approximately $48.2 million with shares climbing 17.5% over two days. CoreWeave rose 18% over the same period with corresponding option premiums exceeding $43 million. Similar large deep-out-of-the-money call option purchases were recorded for SK Hynix, SanDisk, DRAM-related entities, and Intel. These contracts are strategically designed to trigger large-scale gamma squeezes and drive price momentum.

The collapse this summer resulted from the significant downturn in the AI sector, which caused losses running into the tens of billions of dollars for the fund. To survive the crisis, Situational Awareness sold most of its public market positions to Citadel, which allowed the fund to continue operating but signaled a temporary end to its aggressive strategy. In late July correspondence to investors, Aschenbrenner indicated he would wait for another opportunity to act, promising to apply the necessary lessons learned. He stated the fund would continue operating in a hybrid public-private capacity, with public market investments managed on a fully-paid basis. The catastrophic July events have left a deep impression on Wall Street, with previous brokerage partners facing Department of Justice inquiries, effectively blacklisting Aschenbrenner from mainstream financial institutions.

Unlike July's approach that utilized total return swaps with large investment banks to obtain substantial leverage, the current strategy employs flexible options as the primary instrument. Using fully-paid options theoretically limits maximum losses to the premiums already paid, eliminating the risk of margin calls or forced liquidation. However, this structural adjustment does not fundamentally change the strategy's logic — it still involves building large-scale exposure in momentum-driven targets with relatively limited liquidity, aiming to guide market following and trigger chain-reaction price increases. The correlation between spot price advances and rising volatility is becoming a positive return driver for dispersion strategies after recent dramatic fluctuations in select technology stocks.

The central market question is whether this approach will prove successful once again or repeat July's collapse trajectory. This time, Aschenbrenner's gains and losses are entirely his own responsibility, without sharing exposure with brokers through total return swaps. If momentum reverses, option premiums would decline to zero with no leverage adjustment to cushion the impact. The valuation logic for AI storage-related stocks is itself facing challenges, with volatility structures remaining highly sensitive after the summer's sharp correction — any interruption in momentum could trigger rapid deleveraging. Historically, strategies attempting to trigger gamma squeezes through deep out-of-the-money options depend heavily on sustained market participation. Once market participants recognize the position concentration and choose to hedge or sell short, outcomes often run directly counter to initial expectations.