Trader Makes $17M by Betting Against James Wynn’s High-Risk Strategy

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When Betting Against the House Pays Off: A Tale of Two Traders

In the grand theater of crypto, where fortunes are made and lost faster than a tumbleweed in a dust storm, one man’s folly became another’s fortune. James Wynn, a name that echoes through the halls of high-risk trading, found himself down nearly $100 million, while a certain trader, let’s call him 0x2258, danced merrily on the other side of the ledger, pocketing a cool $17 million. Talk about a plot twist! 🎭

Picture this: while Wynn was throwing his chips on the table, betting long on the wild ride of crypto, our hero 0x2258 was playing the opposite game. Shorting when Wynn went long and going long when Wynn shorted—this was not just a strategy; it was a masterclass in counter-intuition. The result? A staggering $17 million in profits for 0x2258, while Wynn was left holding the bag of $98 million in losses. Ouch! 😬

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.

— Lookonchain (@lookonchain) May 30, 2025

This curious tale began on May 24, when 0x2258 decided to short both Bitcoin and Ethereum, much to the chagrin of Wynn, who was riding the bullish wave. The very next day, after Wynn closed his trades, 0x2258 followed suit, locking in a tidy $1.36 million gain. It’s almost like watching a game of chess where one player is always a move ahead. 🕵️‍♂️

But the drama didn’t stop there! Wynn, ever the gambler, flipped to shorting BTC and ETH, while 0x2258, with a grin, went long. When Wynn exited, our clever trader raked in another $2.54 million. This back-and-forth continued until May 26, when Wynn went long again, and 0x2258, ever the opportunist, profited $1.7 million by shorting. It’s like a dance, and 0x2258 had the rhythm! 💃

Wynn’s Risky Bets Cost Him $98 Million

James Wynn, the high-leverage trader with a penchant for risky bets on Hyperliquid, has now amassed losses that would make even the most seasoned gambler weep—about $100 million. Yet, in a twist of irony, he claims to have no regrets about his “casino” adventures. 🎰

“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.

Wynn, notorious for his leveraged trades, has also found himself in hot water due to his involvement with memecoins. Accusations of pumping and dumping these digital tokens have been hurled at him by crypto sleuths, including the infamous ZachXBT. It seems the crypto world is as much about drama as it is about dollars! 💸

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2025-05-30 22:43