Look at the Wall Street game of the old-timers in the crypto circle.

Written by: Azuma

Do you remember "AI Stock God" Leopold Aschenbrenner?

Leopold and his fund Situational Awareness were once the most sought-after new investment myth on Wall Street just a few months ago. However, at the end of July, due to a significant pullback in AI-related stocks and high leverage, the fund faced major losses, forcing it to massively close public market positions and sell off most of its stock portfolio at a discount to Citadel, owned by Ken Griffin.

A magnificent AI investment myth seemed to come to an end, but to the market's surprise, the wingless Leopold did not remain silent. Just over a month after the disastrous defeat, this former "AI Stock God" made a comeback in the public market. Moreover, it's still familiar AI stocks, but this time, he seems to be ready to try a different approach.

"AI Stock God," who is he? (Familiar readers can skip)

In March of this year, we first introduced Leopold in the article “SBF’s Little Brother, turning $225 million into $5.5 billion in a year.”

Leopold worked for Future Fund under FTX in 2022 and remained with the team until FTX's downfall. In 2024, he wrote a 165-page super paper titled "Situational Awareness: The Decade Ahead" and founded the eponymous fund Situational Awareness, serving as Chief Investment Officer.

Situational Awareness focuses on investment opportunities in the AI supply chain. As of Q4 2024, the fund's public holdings were "only" $225 million. However, in the Q4 2025 holdings disclosure announced in February of this year, this number rapidly grew to $5.5 billion; by the Q1 holdings disclosed in May, the figure had risen to $13.7 billion... Although these numbers no longer hold significance today, the nominal total value of the fund’s holdings in the Q2 report just released has reached $20.2 billion.

Odaily Note: It is important to note that the statistics in the U.S. 13F filings reflect the market value of the put options as their corresponding underlying stocks' "Notional Value," rather than the actual premium cost paid by the fund for the options.

With explosive investment returns, Leopold and Situational Awareness gained immense popularity, becoming one of the most discussed AI investment trends on the internet, and Leopold was dubbed the "AI Stock God" by a market eager to idolize him.

A Comeback

The rumors of the "AI Stock God" returning began on September 10, when a set of unusually concentrated AI stock options trades renewed the market's awareness of Leopold.

On that day, U.S. stock analyst Paradis disclosed on X that since last Friday, there had been a series of highly concentrated large customized AI-related option orders (FLEX Options), with a total premium paid of approximately $315 million, corresponding to a Delta exposure of about $1.1 billion and a Vega exposure of about $5.8 million.

• SNDK: January expiration 2040/2200 call options - $57 million premium, $198 million Delta, $1.04 million Vega.
• BE: January expiration 250/310 call options - $48 million premium, $140 million Delta, $565,000 Vega.
• INTC: January expiration 105/115 call options - $48 million premium, $185 million Delta, $870,000 Vega.
• CRWV: January expiration 105/115 call options - $43 million premium, $160 million Delta, $770,000 Vega.
• DRAM: January expiration 65/70 call options - $43 million premium, $173 million Delta, $855,000 Vega.
• SKHY: January expiration 190/210 call options - $39 million premium, $148 million Delta, $710,000 Vega.
• AMD: January expiration 540/580 call options - $36 million premium, $193 million Delta, $1.08 million Vega.

Paradis did not confirm at that time that this was Leopold’s operation but suspected from the structure of the positions (the specific targets highly overlapping with Situational Awareness's previously disclosed public market holdings) that Leopold had indeed returned to the market, emphasizing that Nomura (NMR) and Goldman Sachs (GS) trading desks both believed that these options trades had a "single mysterious buyer" behind them.

Then, CNBC quoted sources confirming that Leopold really was back!

Insiders told CNBC that Situational Awareness has indeed become active again in the options market and has recently re-purchased options related to AMD (AMD), Bloom Energy (BE), CoreWeave (CREV), SK Hynix (SKHY), SanDisk (SNDK), and DRAM ETF (DRAM), with trading activities taking place late last week and early this week.

Clearly, Leopold has not completely changed his judgment on AI investments due to the disaster in July. On the contrary, based on the positions exposed so far, he is still betting on the same main line – AI computing power and infrastructure.

This is also the most noteworthy aspect of Leopold's comeback. The disaster in July does not simply prove that Leopold's judgment on AI was wrong; the truly fatal factors were the combination of directional judgment, concentrated positions, and leverage. It is evident that the returning Leopold is aware of this.

The Core Change: Leverage!

While looking at the currently exposed positions, Leopold's investment direction has hardly changed, but compared to the strategies used before July, he has clearly pulled back significantly this time.

According to a Financial Times report on September 11, Situational Awareness is reconstructing its public market portfolio and has begun cooperating with a new broker, Clear Street. Leopold has indicated to this broker that the fund will use significantly lower leverage than before.

This may be the most direct lesson left by the disaster in July. The previous Situational Awareness had high positions and high leverage in AI stocks; once the market fluctuated against them, losses would quickly transmit to the financing side, forcing them to handle positions at the worst timing.

Instead, this time, he clearly does not dare to do it like that again. In the letter he addressed to investors after the July disaster, Leopold stated that future public market investments would more often adopt a "fully paid-for" approach, which means holding stocks with their own funds or buying options for which the premiums have been fully paid to reduce financing and forced liquidation risks.

This also explains why FLEX Calls occupy a significant position in this time of re-establishing positions. The cost of buying call options is just the premium paid; even if the underlying's ultimate movement is completely opposite, losses are usually locked within this premium. For Leopold, this approach still allows for significant upside exposure but, unlike the previous leveraged positions, does not force liquidation due to margin pressure.

Of course, there’s actually a more pragmatic, even somewhat awkward reason – this time's low leverage is not entirely a result of Leopold's proactive choice.

On September 11, Reuters reported citing insiders that JPMorgan Chase has ended its lending relationship with Situational Awareness, while previously JPMorgan had been one of the major lenders for Situational Awareness... Therefore, Leopold’s reduction of leverage this time has elements of both proactively shrinking risk and responding to changes in financing conditions.

The Second Act of the "AI Stock God"

From $225 million to over $20 billion in public attention, to the crash in July, and now making a comeback in the market, Leopold’s journey is no longer easily summarized by the phrase "AI Stock God." But at least so far, the disaster in July has not made him abandon his judgment on the AI supply chain; rather, it has prompted him to re-examine his positions and leverage.

Of course, lowering leverage does not mean the disappearance of risk. AMD, Intel, SanDisk, CoreWeave, SK Hynix... these are still highly volatile AI trades, and the path Leopold is betting on remains crowded and expensive.

Last time, he lost because he did not wait for the market to fulfill his judgment; this time, whether he can survive to that day might truly be the highlight of the "AI Stock God" second act.