Crypto keeps losing to Ken Griffin’s Citadel

Ken Griffin’s Citadel has bought most of Situational Awareness’ AI stock portfolio at a discount, a move that represents another victory for the billionaire villain of the crypto industry.

Indeed, despite years of criticism about Griffin’s traditional finance tactics, the crypto industry keeps giving him more assets.

From a copy of the US Constitution, payment for order flow, equity in a $40 billion crypto holding company, and a new distressed portfolio of cheap AI stocks, crypto traders are far too willing to further enrich the billionaire CEO.

Margin calls gutted former FTX Future Fund member Leopold Aschenbrenner’s AI hedge fund earlier this week, turning the 25-year-old into a forced seller liquidated under a stack of self-imposed leverage to Griffin’s standing bid.

Griffin, unlike most crypto investors, had plenty of cash amid Aschenbrenner’s distress.

The New York Times reported that Citadel won the overnight auction for Situational Awareness’ AI stocks at a “considerable reduction” to market value.

Crypto has watched this movie before.

Cheap share certificates alongside a cheap US Constitution

When the crypto industry’s people, tokens, or trophies land across the negotiating table from Griffin, more often than not, traders often accept his lowball offer. At the eleventh hour, a little cash is better than nothing at all.

Consider what happened in November 2021 when ConstitutionDAO raised over $40 million of ETH to bid on a physical print of the US Constitution. Over 17,000 donors chipped in at a median of $206 apiece.

Their crowdfunded bid carried a fatal flaw, as Protos noted. Its balance sat on-chain in public view, so rival bidders like Griffin knew precisely where their money to bid would run out.

The DAO also reserved millions for fees and costs that it couldn’t spend on bids.

Griffin won the document at $43.2 million. Sotheby’s irrevocable-bid mechanics trimmed roughly $4.2 million off his final bill. This spring, he bought the only other privately owned first print, cornering the market for the immensely valuable collectible, despite crypto’s attempt to decentralize it.

Thanks for the payment for order flow

Payment for order flow is a predictable profit generator for sophisticated market-makers and quantitative trading companies like Citadel.

Whenever a stock brokerage or similar platform offers commission-free or “$0 fee” trades, they often engage in payment for order flow on the backend.

Citadel Securities has accounted for over 40% of all US payment for order flow in some years, and it’s happy to accept order flow from crypto traders who inefficiently smash buy or sell with “market” orders.

Of course, retail crypto traders also buy stocks and options — the same folks who route even more payment for order flow through Citadel.

On crypto trades, for example, Robinhood discloses that market makers pay it $0.95 per $100 of orders routed. Its SEC filings identify B2C2, Wintermute, and Citadel Securities among the companies paying for order flow.

Ripple equity, cheaper than its own tokens

Consider another example of Griffin’s one-sided crypto dealings.

In November 2025, Ripple raised $500 million at a $40 billion valuation. Affiliates of Citadel Securities co-led the round.

Although the valuation seemed impressive, Griffin wasn’t taking much risk. In fact, $XRP was trading near $2.35 the day of the announcement.

That day, Ripple held roughly 37 billion $XRP, a pile worth about $87 billion that day.

In other words, Citadel bought shares in a company valued at less than half its crypto holdings.

In addition to his incredibly discounted valuation, Griffin also received protections from the price risk of $XRP itself.

Bloomberg reported the fine print that benefitted Citadel. Absent an IPO or sale 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.

Citadel’s rights also stand ahead of existing shareholders in the event of any liquidation.

In summary, crypto has gifted Ken Griffin and Citadel a cheap portfolio of AI stocks, a cheap Sotheby’s art piece, cheap payments for order flow, and cheap equity at less than half its balance sheet.

Despite describing crypto in October 2021 as a “jihadist call” against the US dollar, it’s been paying him ever since.