News 
May 30, 2025 
4 min. 
While crypto fund manager James Wynn reportedly lost close to $100 million through a series of high-stakes trades, one savvy trader quietly amassed a fortune by consistently taking the opposite side.
According to on-chain analytics platform Lookonchain, the wallet identified as 0x2258 netted over $17 million in profits by systematically mirroring and countering Wynn’s moves. The data, published on Friday, May 30, shows the trader built this windfall by shorting when Wynn went long, and going long when Wynn shorted.
This strategic opposition first caught attention on May 24, when 0x2258 shorted both Bitcoin and Ethereum as Wynn opened long positions. By the next day, after Wynn closed out, 0x2258 exited as well—securing a $1.36 million gain.
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Wynn then shifted to shorting BTC and ETH. Once again, 0x2258 did the opposite and went long. When Wynn closed his trades, the counter-trader walked away with another $2.54 million in profit. The pattern repeated until May 26, with 0x2258 bagging an additional $1.7 million by shorting while Wynn returned to long positions.
Wynn’s losses reportedly reached $98 million, making this one of the most high-profile examples of successful counter-trading in recent crypto history.
James Wynn’s High-Stakes Trades Result in $98M Loss Amid Memecoin Controversy
Crypto trader James Wynn, known for his aggressive use of leverage on platforms like Hyperliquid, has now recorded losses nearing $100 million. This marks his most significant setback to date. Despite the staggering figure, Wynn remains unapologetic.
“Zero regrets. Flipping $4 million to $100 million and back down to -$13 million is one hell of a thrill. Hope many of you enjoyed it as much as I did,” Wynn remarked, referring to the volatile trading spree that has drawn both attention and criticism from the crypto community.
Wynn, who rose to prominence through high-risk trades, is no stranger to controversy. Beyond his leverage-heavy strategy, he has faced allegations of participating in pump-and-dump schemes involving memecoins. Notably, crypto sleuth ZachXBT and other on-chain investigators have accused him of promoting tokens to followers before selling his own holdings for profit.
Despite the losses and scrutiny, Wynn remains a polarizing figure in the space. Some view him as a fearless trader, while others see him as a cautionary tale of speculative excess.
