By betting against James Wynn, this trader made $17 million in under a week
A crypto trader has quietly earned over $17 million by consistently betting against one of Hyperliquid’s most-watched figures, James Wynn, whose high-risk strategy backfired with nearly $100 million losses.
On May 30, blockchain analysis platform Lookonchain reported that a trader using the wallet address 0x2258 has been tracking Wynn’s activity and executing reverse trades.
This means the unnamed trader consistently shorted when Wynn took long positions and went long when Wynn turned bearish.
The trading strategy
The trading activity began to draw attention on May 24, when 0x2258 shorted Bitcoin and Ethereum while Wynn maintained a long position on BTC. By May 25, after Wynn closed his long position, 0x2258 exited his shorts with a $1.36 million profit.
Later that same day, Wynn switched to shorting Bitcoin. In response, the whale flipped long on both BTC and ETH. When Wynn closed his short the next day, 0x2258 exited his long positions with an additional $2.54 million in gains.

The pattern continued on May 26 when Wynn went long again. This prompted 0x2258 to short BTC and ETH, resulting in an unrealized profit of $1.7 million.
The series of calculated counter-trades has helped the anonymous trader amass more than $17 million in profit while Wynn’s own positions sank further.
Wynn’s losses
On the other hand, Wynn saw his fortunes collapse after a massive liquidation triggered by Bitcoin’s drop to nearly $105,000. This resulted in the high-profile trader losing around $98 million.

Despite the setback, Wynn’s remains unfazed, saying:
“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.”
Over the past week, Wynn has drawn attention for his risky, high-leverage plays on Bitcoin on the decentralized trading platform, Hyperliquid.
As of press time, Wynn has reopened a $47 million long on Bitcoin and a $8.4 million PEPE long, both using 10x leverage.
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