Trader makes $17M by betting against James Wynn’s high-risk strategy

While James Wynn lost nearly $100 million, another trader made a fortune by consistently taking the opposite side of his trades. One crypto trader earned more than $17 million by betting against controversial crypto fund manager James Wynn. On Friday, May 30, Lookonchain reported that the trader behind wallet address 0x2258 repeatedly mirrored the opposite of Wynn’s positions. The trader shorted when Wynn went long and went long when Wynn shorted. The approach paid off, resulting in $17 million in profits while Wynn racked up $98 million in losses. The winning strategy lately? Do the opposite of James Wynn. 0x2258 has been counter-trading James Wynn—shorting when James Wynn goes long, and going long when James Wynn shorts. In the past week, 0x2258 has made ~$17M, while James Wynn has lost ~$98M. https://t.co/NhOE1YD4QN pic.twitter.com/aO13boYza2 — Lookonchain (@lookonchain) May 30, 2025 This strategy started drew attention on May 24, when 0x2258 shorted both Bitcoin and Ethereum, contrary to Wynn’s long positions. The next day, after Wynn closed his trades, 0x2258 followed suit, locking in a $1.36 million gain. You might also like: From PEPE to Billions: meet crypto’s boldest whale James Wynn Wynn then flipped to shorting BTC and ETH, while 0x2258 went long. When Wynn exited, the counter-trade earned 0x2258 another $2.54 million. This continued until May 26, when Wynn went long again and 0x2258 profited $1.7 million by shorting. Wynn’s risky bets cost him $98 million James Wynn is a well-known high-leverage trader whose risky trades on Hyperliquid have led him to the biggest losses yet, now amounting to about $100 million. Still, the trader stated that he had no regrets over the “casino.” “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,” James Wynn said . While being well-known for his leveraged trades, Wynn is also a controversial figure due to his involvement in memecoins. He was accused by several crypto investigators, including ZachXBT, of pumping and dumping memecoins to his followers. You might also like: James Wynn longs PEPE with 10x leverage as PEPE price eyes potential 20% – 40% leg up

Source: crypto.news