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James Wynn Returns to High-Stakes Crypto Trading After Major Losses
James Wynn, a prominent figure in the cryptocurrency trading community, has made headlines once again after taking a daring $100 million, 40x-leveraged long position on Bitcoin—just days after incurring nearly $100 million in losses. Wynn continues to demonstrate his high-risk, high-reward trading approach, captivating the attention of blockchain enthusiasts and crypto investors worldwide.
Profitable HYPE Trade Sets the Stage
According to data from Lookonchain, Wynn recently unstaked and sold 126,116 Hyperliquid (HYPE) tokens, valued at approximately $4.12 million. He acquired these tokens earlier in May at an average price of $24.4 and sold them at $32.7, netting an impressive profit of over $1 million. While this trade marks a notable win, it is substantially outweighed by the significant losses Wynn experienced last week.
From Massive Gains to a Near $100 Million Wipeout
On-chain analytics provided by Spot On Chain reveal that Wynn’s tumultuous week followed a period of remarkable success. Between March 20 and May 23, Wynn accumulated $83 million in profits through leveraged trades, making headlines with positions such as a 10x long on PEPE with $23.8 million in unrealized gains, a 10x long on Trump (TRUMP) for $6.83 million realized, and a 5x long on Fartcoin (FARTCOIN) yielding $4.48 million.
His boldest play came on May 22, when Wynn’s $1.14 billion long position on Bitcoin (BTC) soared to a $39 million open gain. However, the tides quickly turned: Wynn doubled down, increasing his BTC long to $1.25 billion, but faced a $13.4 million loss within hours. The next day, a switch to a $1 billion short position ended with an additional $15.87 million loss in less than a day. The downfall culminated on May 30, as BTC dipped below $105,000, liquidating Wynn’s 949 BTC position worth $99.3 million. His net performance swung from $83 million in profits to approximately $12 million in total losses over just one week.
Reentering the Market with Aggressive Leverage
Undeterred, Wynn quickly reentered the arena, this time betting on a 945 BTC long position—equivalent to $99.7 million—on the Hyperliquid platform, using 40x leverage. His initial margin was $2,177,955.53 with a liquidation price set at $104,577. An additional $400,000 deposit slightly lowered his liquidation price to $104,151, putting his position less than 1% from current Bitcoin market levels.
Wynn Rallies Community Support Amid Whale Activity Concerns
After placing his high-stakes bet, Wynn took to X (formerly Twitter), urging his followers to support him by buying Bitcoin. He speculates that both he and other retail traders using high leverage on Hyperliquid are being targeted by large crypto whales seeking to trigger liquidations.
'As soon as I entered my long position, it felt like immediate hunting,' Wynn shared online, suggesting, 'There is an agenda here, and I don’t quite know what it is. Maybe it’s because I’m a small trader in a whales’ game, or perhaps it’s because I’m drawing attention to Hyperliquid.'
The crypto community continues to watch Wynn’s actions closely, as his high-profile trades offer a thrilling look into the volatility and opportunity in the cryptocurrency markets.

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