How Wall Street Sussed Out That Situational Awareness Was On the Ropes
From whispers of an Anthropic stake sale to strange options moves, traders sensed trouble and swung into action
- Leopold Aschenbrenner’s hedge fund, Situational Awareness, faced steep losses from tumbling AI stocks and margin calls from lenders in late July.
- The fund lost about 67% in July, which amounted to roughly $30 billion, after its concentrated long and short stock bets moved against it.
- To raise cash, Situational Awareness sold the bulk of its leveraged stock portfolio to Citadel at a discount of about 10% to public market prices.
David Mann was in a taxi heading to LaGuardia Airport when he heard the news: Wall Street’s AI wunderkind was in trouble.
It was the afternoon of Wednesday, July 29, and Mann got a call from someone working on behalf of Leopold Aschenbrenner’s hedge fund, Situational Awareness, asking if he wanted to buy a piece of the fund’s stake in Anthropic, the AI powerhouse. A deal needed to be done overnight, Mann was told.
Mann realized what was happening—nobody sells pre-IPO shares in a company valued at nearly $1 trillion unless they are on the ropes.
“Aschenbrenner was being forced to sell,” said Mann, chief executive of the Mannsion Group, a family office that owns stakes in Anthropic and other private companies. “He needed the money and was sounding people out.”
For two years, Aschenbrenner, a 20-something former OpenAI employee, was on a roll. At his peak, his fund controlled some $100 billion in assets, including the enormous sums he was borrowing from banks to supersize his AI stock bets, from semiconductors to software. Buzz that he was an AI Nostradamus helped the effort.
By late July, the chatter had changed—Aschenbrenner was facing steep losses from tumbling AI stocks, and he was desperate for a way out of his investments, according to people familiar with the situation. Banks were issuing margin calls, or demands for more collateral to back their lending. Elite investors including Steve Cohen and Daniel Loeb heard of the Anthropic sale. Short sellers were targeting Aschenbrenner’s favorite stocks.
“It felt like he was being hunted,” says John Pfeffer, co-founder of Pfeffer Capital, a family office that has invested in Situational since its inception.
The swift unwind of Situational shows how quickly information can spread across Wall Street when a trader is in trouble—and how fast it can lead to an avalanche of selling. It is a brutal lesson, too, in the risks of leverage, or investment bets fueled by borrowing, several years after Archegos Capital’s implosion.
Aschenbrenner built his firm on his reputation as an AI soothsayer. Others pointed to lengthy investing track records when launching hedge funds or venture-capital funds; Aschenbrenner’s stature stemmed from a 165-page essay in 2024, “Situational Awareness: The Decade Ahead,” that foresaw the path of AI’s development.
From the beginning, his firm promised to make concentrated bets on stocks that would benefit from AI’s broad adoption, from chip makers to infrastructure providers, while betting against stocks that would be disrupted by AI, including software makers.
“It wasn’t for conservative pension funds and retired teachers,” Pfeffer said. “It was going to be an aggressive bet on AI, we all knew there was going to be volatility.”
Aschenbrenner got a helping hand from Wall Street. Lending to hedge funds is giving bank earnings a boost, and a number of banks were eager to back a new manager trading the market’s hottest theme.
Goldman Sachs financed Situational’s trades from the outset while featuring the fund at its emerging-manager conference at the Orlando Ritz-Carlton in March 2025.
Aschenbrenner didn’t have the pedigree of some other managers. Still, Goldman executives prized Situational, they told clients, though the bank monitored the fund because its portfolio was so concentrated and levered, according to a person familiar with the matter.
Aschenbrenner made the rounds of other banks alongside David Geffen, a former financing executive at BlackRock and Amaranth Advisors who ran a hedge-fund advisory firm, people familiar with the situation said. JPMorgan, Bank of America and Citigroup also lent money to Situational. Morgan Stanley was in talks to add him as a client in the coming months.
Some banks had concerns, though. While investors often hedge risk by holding “long” positions that certain stocks will rise as well as “short” positions that others will fall, Situational’s longs and shorts amplified a bet on a single theme. That is sometimes called a “Texas hedge.”
Banks including Jefferies and Barclays passed on the fund. One prime brokerage executive who declined to take it on as a client after meeting with Aschenbrenner said his unshakable confidence was a red flag.
As it grew from about $1.5 billion in assets under management last summer to over $45 billion at the start of July, Situational borrowed about $3 for each $1 of capital it held, and sometimes even more, people familiar with the matter said, above the leverage used by funds trading such volatile kinds of shares.
Situational also purchased “flex options,” a customized derivative, to amplify its AI trade.
For a while, it relied on a shoestring team that included two analysts, an economist, a director of research and a risk manager. In recent months, the fund hired more experienced executives to run areas such as compliance, investor relations and finance, including Sven Khatri, a former treasury researcher at Citadel.
Investors flocked to the fund, thanks to its outsize returns. By the middle of July, though, investor sentiment around the AI trade had shifted, as advances in cheaper, open-source Chinese models spooked traders. Situational’s lenders began examining their exposure to the firm and its swings in performance. Rival traders said they paid attention to what Aschenbrenner owned, so when those stocks took a dive they surmised that he was in trouble.
Situational had discussed a “crash put” program inspired by Jane Street’s similar program meant to protect against a violent market decline, one person briefed on the program said. One way to achieve that could be to purchase a high volume of puts against a semiconductor index, giving the fund the right to sell at a set price, said market participants.
But stocks that Situational owned as of its most recent filings, including fuel-cell maker Bloom Energy, memory chip maker Sandisk and AI cloud company Nebius, dropped throughout July, then went into free fall starting on Friday, July 24. Software stocks that Situational had bet against, including Adobe, AppLovin and Figma, started to rally, exacerbating losses, people familiar with the situation said. Traders noticed unusually high volumes of put options related to companies meant to protect against the fund’s declines.
That day, Situational sent a second-quarter update to clients telling them it had suffered losses in July but that it was a good time to invest new money in the fund. Rumors spread that the fund was under severe stress, prompting nervous clients to call its office with urgent questions. One investor was told by a fund executive that it was reducing its risk.
As the week of July 27 began, Situational was selling shares to raise cash to meet margin calls from lenders, said people familiar with the matter. Nebius, Bloom Energy, Sandisk and Core Scientific fell between 9% and 24% between Friday, July 24 and Tuesday, July 28.
By Wednesday, July 29, it was an open secret on Wall Street that at least one major fund was “degrossing,” or selling a massive amount of shares to reduce leverage and risk. Each day, prime brokers share reports with their customers with the aggregate details of the portfolios of their hedge-fund customers. That month, the reports pointed to a decrease in leverage in the tech sector, tipping traders off that someone focused on those stocks was likely in trouble.
Scrambling for cash, Aschenbrenner and his team began emergency talks to sell at least part of its $5 billion Anthropic stake. But Situational was constricted: Anthropic had the right to approve of any transfer of its privately held shares, so the fund could only pitch those with existing stakes in Anthropic.
That same Wednesday, Situational approached firms including Sequoia, Greenoaks, Michael Dell’s family office DFO Management, and New York investment firm XN about buying its Anthropic stake, people familiar with the talks said. Situational offered a 20% discount and gave a 12-hour deadline.
The Greenoaks group worked through the night to get the deal done. It was scheduled to close at 8 a.m. the next morning. Anthropic signed off on a sale of the stake.
The investors bidding on the Anthropic stake didn’t realize it, but Situational simultaneously was negotiating a very different deal with hedge funds Citadel and Millennium Management: the sale of the bulk of its stock portfolio.
A Citadel executive reached out to Khatri at Situational on July 28. Talks between the two firms the following day progressed from Citadel purchasing the entirety of Situational’s liquid stock portfolio for cash to the firm only buying Situational’s positions that were financed with leverage, according to people familiar with the discussions.
Ken Griffin joined the conversations from London. Aschenbrenner, sensing there could be upside after his crisis subsided, wanted to keep as much of his stock portfolio as possible.
Citadel won that deal in the early hours of Thursday, July 30, paying a 10% or so discount to public market prices at the time.
That morning, Aschenbrenner reached out to investors who had been expecting to close shortly on the Anthropic stake, saying he had reached a better deal with Citadel, people familiar with those conversations said. Some investors were angry.
Situational and Citadel finished signing documents and trade confirmations around 9:10 a.m., leaving only about 20 minutes before U.S. markets opened.
Situational gave its investors the bad news: The fund lost about 67% so far that month—roughly $30 billion—though it remained up 80% for the year. Its investors are tallying their own losses. Jane Street, the powerhouse Wall Street trading firm that is one of Situational’s investors, lost about $15 billion in July, much of it due to Situational’s troubles.
That weekend, Aschenbrenner wed Avital Balwit, chief of staff to Anthropic founder Dario Amodei, in a seaside ceremony in Carmel, Calif. One reference in a toast, made half in jest, was to Griffin and Citadel for making the day possible, according to an attendee.
Aschenbrenner and his leadership team are in the process of meeting clients to explain how the fund lost so much, so quickly, people familiar with the matter said. The executives said they were doing a postmortem on what had happened, and that the fund was reassessing how much risk it would embrace in the future.
Aschenbrenner’s fund—now managing about $15 billion—is also rebuilding its portfolio. Situational recently invested $400 million in startup Source Foundry and has been buying shares of SharonAI.