Approximately $96 million in short-term call options poured into four AI chip stocks 鈥?SanDisk, Micron, Intel, and Marvell 鈥?on Friday, with SanDisk momentarily spiking as much as 11% during the trading session.

Observing this surge of short-dated options activity, CNBC host Jim Cramer took to social media platform X to exclaim, "The way this looks, it's like Leopold is back!"

If you have been tracking investment opportunities in the global AI compute and large language model arena, the name Leopold Aschenbrenner should be familiar to you.

The former key researcher at OpenAI, who later founded the AI-focused hedge fund Situational Awareness with a luminary reputation, is notorious for deploying extreme leverage to aggressively purchase short-dated call options on semiconductor and AI companies. In 2024, his fund launched with roughly $225 million and, through high-leverage AI bets, ballooned to approximately $45 billion.

However, July of this year brought a catastrophic reversal. The fund suffered a 67% crash during the AI sector's correction, forcing it to offload a substantial portion of its holdings to Citadel. The Financial Times ranked this event as one of the largest single losses in hedge fund history. Despite this, the fund still finished the year with a positive return of roughly 80%.

In late July, Aschenbrenner communicated to investors in a letter his intentions to "bide time for another battle" and "learn the necessary lessons," while pledging that public market investments would be managed on a "fully paid basis."

Last week, CNBC reported the fund had re-entered options positions in stocks such as AMD, Bloom Energy, and CoreWeave. This time, however, the focus has shifted back to memory and chips 鈥?the two sectors that were its largest positions before the crash.

Breaking down the near-$100 million call options purchase, intraday trading data aggregated by ZeroHedge reveals the following details for contracts expiring on October 2nd: Micron (MU): strike price of 1000, roughly 10,000 contracts, with premiums around $44 million. SanDisk (SNDK): strike price of 1600, approximately 4,200 contracts, with premiums of about $41 million. Intel (INTC): strike price of 115, nearly 20,000 contracts, with premiums near $7.3 million. Marvell (MRVL): strike price of 250, roughly 3,500 contracts, with premiums around $3.85 million.

SanDisk was trading around its strike price at the time, already above it, while Micron sat at approximately 990, making its strike nearly at-the-money. Intel and Marvell's strike prices were slightly above their current prices. Weekly highs for Micron and SanDisk were recorded at 1255 and $2354 respectively, indicating current prices still have considerable distance from those peaks.

With only two weeks until expiration, time decay and gamma sensitivity are extremely high, leaving almost zero room for error in directional calls.

Cramer pointed out that the October expiration falls after Micron's fiscal fourth-quarter earnings report, an event that historically moves the entire memory sector. He has maintained a bullish view on this sector since August, arguing that AI data center demand and supply discipline are reshaping the traditional boom-bust cycle of the memory industry.

While SEC filings have yet to disclose the buyer's identity, there are solid reasons for market speculation pointing to Aschenbrenner.

The most direct clue lies in the underlying assets. Situational Awareness's regulatory filings from late June showed positions of approximately $5.7 billion in SanDisk and $5.6 billion in Micron, making them its two largest holdings. This batch of nearly $100 million in options premiums is concentrated in those exact same two stocks.

The trading methodology also aligns. The fund was previously known for employing exceptionally high leverage to bet on AI momentum, at times reaching 400% leverage. Short-dated, massively sized call options are its signature tool 鈥?using large purchases to trigger market makers' gamma hedging buys, pushing stock prices to spike in the short term.

The timeline also fits seamlessly. According to a September 11 Financial Times report, Aschenbrenner has rebuilt positions via Flexible Options in assets including AMD, Intel, SK Hynix, SanDisk, and CoreWeave. Nomura strategist Charlie McElligott captured the signal at the time, noting a cumulative $315 million in options premiums flowing into AI and semiconductor names over multiple days, involving $1.1 billion in delta exposure. He also observed that call skew for semiconductor ETFs over the next three months had surged to historic highs.

Although the tools have changed, the underlying logic remains intact. Unlike July when he relied on total return swaps (TRS) from major banks like Goldman Sachs for leverage, Aschenbrenner is now believed to be using fully-paid options, where the maximum loss is limited to the premiums already paid, theoretically eliminating margin calls or forced liquidation risks.

This shift is grounded in practical necessity. Following the crash, JPMorgan terminated its lending relationship with the fund, the SEC has requested information from banks that financed the fund, and a previously partnered broker is under investigation by the U.S. Department of Justice. According to the Financial Times, Aschenbrenner has shifted to Clear Street, a tech-sector-focused broker, to re-establish cooperation.

But the strategic playbook has not fundamentally changed. McElligott observed that this batch of trades exhibits a pattern of "spot rising alongside volatility" 鈥?which is highly reminiscent of the market behavior seen before July's crash. It still involves establishing massive, concentrated exposure in momentum names with limited liquidity, with the intent of igniting a chain reaction of upward price moves. Should momentum reverse, the premiums would go to zero instantly, with no ability to cushion the blow by adjusting leverage.

The fund's 13F filing for the third quarter is due in mid-November. Only then will regulatory documents confirm the true buyer of these trades.