TLDR
- Crypto trader James Wynn lost $99 million in liquidations from highly leveraged Bitcoin positions on HyperLiquid exchange
- Wynn had initially grown $500,000 to $87 million through successful meme coin trades before the Bitcoin losses
- A counter-trader identified as 0x2258 made $17 million by betting against Wynn’s positions over three days
- The liquidation occurred despite Bitcoin trading in a narrow 2% range, with poor trade execution cited as the cause
- Bitcoin long liquidations exceeded $200 million in 24 hours as price volatility increased around $105,000 level
High-leverage crypto trader James Wynn suffered a catastrophic $99 million loss on the HyperLiquid decentralized exchange after his Bitcoin positions were liquidated. The trader, who operates under the handle JamesWynnReal, saw his leveraged bets collapse over a seven-day period ending May 30.
ARKHAM ALERT: JAMES WYNN HAS JUST BEEN LIQUIDATED FOR $100 MILLION DOLLARS pic.twitter.com/dJNCUmbgZO
— Arkham (@arkham) May 30, 2025
Wynn had built a reputation as a successful high-risk trader earlier this year. Between March and May, he transformed $500,000 into $87 million through leveraged positions on meme coins including PEPE, TRUMP, and FARTCOIN. His 10x long position on PEPE alone generated $23.8 million in unrealized profits.
The trader’s Bitcoin strategy began promisingly on May 22 when his $1.14 billion position showed $39 million in unrealized gains. However, the situation deteriorated rapidly over the following week. On May 24, Wynn doubled down with $1.25 billion in Bitcoin longs, resulting in a $13.4 million unrealized loss within hours.
The following day brought another strategic reversal. Wynn switched to $1 billion in Bitcoin shorts, which led to a $15.87 million loss in just 15 hours. The final blow came on May 30 when 949 Bitcoin worth $99.3 million were liquidated as the cryptocurrency dropped below $105,000.
Trading Execution Problems
According to pseudonymous trader Pentoshi, Wynn’s liquidation differed from typical high-leverage failures. Bitcoin remained within a narrow 2% trading range during the liquidation period, suggesting execution issues rather than market volatility caused the losses. “He was super loud on the timeline and yapped a lot, which probably brought a lot of attention he didn’t need,” Pentoshi noted.
Watching this take place, is basically how I've seen almost every leverage trader blow up over time. Well this one is a bit different. But the gist is that you get into a position, a losing one and you are never willing to let it go.
Eventually the market turns against you and… pic.twitter.com/W964hLXreR
— 🐧 Pentoshi (@Pentosh1) May 30, 2025
The HyperLiquid platform showed Wynn’s wallet, beginning with “0x507,” had initially deposited $3 million in stablecoins two months prior. His average Bitcoin entry price reached $108,000 with the position experiencing a $32 million drawdown as prices fluctuated.
Counter-Trader Profits
While Wynn suffered massive losses, another trader capitalized on his misfortune. A trader identified as 0x2258 made $17 million by consistently taking opposite positions to Wynn’s trades. This counter-trading strategy proved highly profitable over the three-day period.
The broader market saw increased liquidation activity during this period. Data from Coinglass showed Bitcoin long liquidations exceeded $200 million in 24 hours as price volatility returned to the cryptocurrency market.
Wynn had previously gained attention for correctly predicting PEPE’s rise to a $4.2 billion market cap in 2023. The meme coin later peaked at over $11 billion in December 2024. He has also promoted the Moonpig meme coin and related gaming project Moonrush, though he denied recent accusations of token dumping.
HyperLiquid operates as a decentralized exchange built on Arbitrum, offering high-speed trading features and transparent wallet activity tracking. The platform has attracted attention from high-leverage traders seeking advanced derivatives trading capabilities.
Bitcoin currently trades at $106,020, down 1.9% over the past 24 hours according to CoinGecko data. The recent price action occurred as market participants monitor ongoing legal developments regarding potential tariff implementations.
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