While high-profile crypto trader James Wynn suffered nearly $100 million in losses from his high-leverage positions, another savvy trader capitalized by consistently taking the opposite side of Wynn’s bets earning over $17 million in the process.
According to Lookonchain’s report on May 30, the trader controlling wallet address 0x2258 carefully mirrored the inverse of Wynn’s trades. Whenever Wynn went long, 0x2258 shorted, and whenever Wynn shorted, the trader went long. This contrarian strategy proved remarkably profitable, generating $17 million in gains while Wynn’s aggressive bets resulted in losses nearing $98 million.
The pattern first attracted attention on May 24 when 0x2258 shorted both Bitcoin and Ethereum, directly opposing Wynn’s long positions. The following day, after Wynn closed out his trades, 0x2258 locked in a $1.36 million profit. Wynn then switched to shorting BTC and ETH, prompting 0x2258 to go long, resulting in an additional $2.54 million gain once Wynn exited those trades. The back-and-forth continued through May 26, with Wynn returning to long positions and 0x2258 profiting $1.7 million by shorting.
James Wynn is widely recognized as a high-leverage trader on Hyperliquid, known for taking aggressive, risky positions. Despite his significant losses, Wynn expressed no regrets about the rollercoaster ride. “Zero regrets. Flipping $4 million to $100 million and back down to -$13 million is one hell of a thrill,” he tweeted, adding that he hoped others found the spectacle entertaining.
Beyond leveraged trading, Wynn is a controversial figure in the crypto community. Several crypto investigators, including well-known analyst ZachXBT, have accused him of manipulating memecoin markets through pump-and-dump schemes targeting his followers.
This episode serves as a cautionary tale about the dangers of excessive leverage in crypto trading, while highlighting how observant traders can profit by countering high-risk strategies.
