Citadel’s pattern of discounted crypto deals exposes market-structure gaps
From ConstitutionDAO to Ripple equity and a forced AI-stock sale, Citadel keeps extracting value crypto's opaque structures failed to protect.
Ken Griffin’s Citadel has again emerged on the favourable side of a distressed crypto-adjacent transaction, buying the liquidated AI-stock portfolio of Leopold Aschenbrenner’s Situational Awareness Fund at what the New York Times described as a “considerable reduction” to market value. The forced sale, triggered by margin calls this week, is the latest in a series of deals in which sophisticated market-making infrastructure has captured value from crypto-linked counterparties operating with thinner cash buffers and less transparent risk controls.
Aschenbrenner’s fund, which had built leveraged exposure to semiconductor and AI equities, was liquidated into Citadel’s standing bid after margin pressure left it with no alternative buyer offering comparable liquidity at short notice. The episode follows PoundToken’s earlier reporting on Citadel’s rescue financing tied to the same fund’s unwind, and on the broader leverage risk building up at bitcoin miners repositioning as data-centre operators.
A recurring pattern since ConstitutionDAO
The dynamic is not new. In November 2021, ConstitutionDAO raised more than $40 million in ether from over 17,000 contributors, at a median pledge of $206, to bid for a rare printed copy of the US Constitution. Because the DAO’s treasury balance sat visibly on-chain, rival bidders — including Citadel’s Griffin — could see precisely how much capital remained available before the crowdfunded campaign ran out of firepower.
Griffin ultimately won the document for $43.2 million, with Sotheby’s irrevocable-bid arrangements reducing his final outlay by roughly $4.2 million. Earlier this year he also acquired the only other privately held first print of the same document, consolidating control of a collectible that crypto enthusiasts had explicitly tried to keep decentralised.
Payment for order flow and a discounted Ripple stake
Citadel Securities has separately built a durable revenue stream from payment for order flow, reportedly accounting for more than 40% of all US order flow payments in some years. Retail brokerages that route crypto and equity orders to market makers, including Robinhood, disclose paying $0.95 per $100 of order value to firms such as B2C2, Wintermute and Citadel Securities — meaning inefficiently executed retail crypto trades continue to subsidise the same market-making apparatus.
The most striking recent example concerns Ripple. In November 2025, the company raised $500 million at a $40 billion valuation, with Citadel Securities affiliates co-leading the round. On the day of the announcement, XRP traded near $2.35, meaning Ripple’s own treasury of roughly 37 billion XRP was worth approximately $87 billion — more than double the valuation at which new investors, including Citadel, bought in.
Bloomberg reported that the round also carried downside protection for investors: absent an IPO or sale within a set number of years, participants could put their shares back to Ripple at a guaranteed positive annual return, with claims ranking ahead of existing shareholders in any liquidation.
What it means for market structure
Taken together, the pattern points less to any single misjudgement by crypto participants than to structural weaknesses that recur across the sector: publicly visible treasury balances that telegraph bid ceilings, thin liquidity buffers that force distressed sellers to accept below-market prices, and private-placement terms that let sophisticated counterparties price in protection crypto holders typically lack. Griffin, who once described crypto as a “jihadist call” against the dollar, has nonetheless profited from each iteration of these gaps.
For regulators weighing disclosure standards for digital-asset treasuries and private crypto-company funding rounds, the episodes offer a concrete illustration of why transparency without matching liquidity protection can leave retail-aligned entities structurally disadvantaged against established market makers.
Read more: Citadel’s $5.5bn rescue of Aschenbrenner’s AI fund exposes bitcoin miner leverage
