Citadel buys most of Situational Awareness’ AI stock book at a discount
Ken Griffin’s Citadel has bought most of Situational Awareness’ AI stock portfolio at a discount, according to Protos, which framed the deal as another instance of Griffin ending up on the favorable side of transactions connected to the crypto sector.
The report says margin calls hit the AI hedge fund linked to former FTX Future Fund member Leopold Aschenbrenner earlier this week. Aschenbrenner, 25, was described as a forced seller after being liquidated under what Protos called a stack of self-imposed leverage, while Griffin had cash available during the distress.
According to The New York Times, Citadel won the overnight auction for Situational Awareness’ AI stocks at a “considerable reduction” to market value.
The article also cites a July 30, 2026 post on X from threadguy, which claimed that two days earlier Ken Griffin or Citadel had publicly declared that the Federal Reserve would raise rates, pressuring semiconductors and AI shares and adding strain on Leopold and Situational Awareness before the firm liquidated its entire public equities book through a transaction. That statement appears in the embedded post referenced by Protos.
ConstitutionDAO’s 2021 auction loss
Protos argues that crypto participants have been in this position before. It points back to November 2021, when ConstitutionDAO raised more than $40 million in ETH to bid on a physical print of the US Constitution.
More than 17,000 donors contributed, with a median contribution of $206. Protos says the crowdfunded effort had a fatal flaw: its balance was visible on-chain, allowing rival bidders, including Griffin, to see exactly where its bidding capacity would run out. The DAO had also reserved millions for fees and related costs that could not be used in the auction itself.
Griffin won the document at $43.2 million. Protos says Sotheby’s irrevocable-bid mechanics reduced his final bill by roughly $4.2 million. This spring, he bought the only other privately owned first print, giving him control of that collectible market despite crypto’s attempt to decentralize ownership.
Payment for order flow remains a profit engine
The report also points to payment for order flow as a recurring source of profit for Citadel. Protos says market makers and quantitative trading firms such as Citadel can generate predictable returns from the model.
When brokerages or similar platforms advertise commission-free or “$0 fee” trades, they often rely on payment for order flow behind the scenes. In some years, Citadel Securities accounted for more than 40% of all US payment for order flow, the article says, and it benefits from crypto traders who place market orders to buy or sell inefficiently.
Retail crypto traders also trade stocks and options, sending more order flow into that system. On crypto trades, Robinhood discloses that market makers pay it $0.95 per $100 of routed orders. Its filings with the US Securities and Exchange Commission name B2C2, Wintermute, and Citadel Securities among the firms paying for order flow.
Protos also references its earlier pieces titled “Short squeeze target Citadel wants to be a cryptocurrency market maker” and “Ken Griffin wants the SEC to follow Citadel’s advice about DeFi.”
Ripple equity bought below the value of its token holdings
Another example in the article concerns Ripple. Protos says that in November 2025, Ripple raised $500 million at a $40 billion valuation, with affiliates of Citadel Securities co-leading the round.
Protos argues that Griffin was taking limited risk in that deal. On the day of the announcement, XRP was trading near $2.35, the report says. Ripple held roughly 37 billion XRP at the time, which would have been worth about $87 billion at that price.
On that basis, Citadel bought shares in a company valued at less than half of its crypto holdings. Protos adds that Griffin also received protections against XRP price risk through the deal terms.
According to Bloomberg, if no IPO or sale took place within a few years, those Ripple investors would have the right to put their shares back to the company at a positive annual rate of return. In a liquidation, the article says, Citadel’s rights would also rank ahead of existing shareholders.
How Protos sums it up
Protos concludes that crypto has handed Ken Griffin and Citadel a discounted AI stock portfolio, a cheaper Sotheby’s collectible, payment for order flow, and equity priced below half of the value of the issuer’s balance-sheet crypto holdings.
The article closes by noting that Griffin described crypto in October 2021 as a “jihadist call” against the US dollar, yet, in Protos’ telling, the sector has continued to enrich him through subsequent deals.