Crypto Trader Faces $100 Million Loss on Bitcoin Bet

James Wynn, a trader once hailed for his wild wins during the memecoin frenzy, just hit a painful milestone — nearly $100 million erased in a matter of days.

Known for turning heads with his risky plays, Wynn’s latest gamble was a massive leveraged long position on Bitcoin. He bet big — reportedly using up to 40x leverage — expecting the cryptocurrency to climb. Instead, Bitcoin slipped below $105,000 on May 30, triggering one of the most brutal liquidations seen on the Hyperliquid platform.

On-chain trackers like Hypurrscan reveal the scale of the damage: more than 940 BTC across multiple trades, gone. Two positions alone — valued at over $99 million combined — were forcefully closed as the market dipped near $104,000. The losses weren’t isolated either. A smaller $10 million trade had already been wiped out the previous day.

The fallout followed Wynn’s bold decision to scale his position to an astonishing $1.25 billion on May 24, a move that left him dangerously exposed to market swings. Just days later, news of potential U.S. tariffs triggered fresh volatility — and the collapse of Wynn’s bet.

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Rather than issue a detailed response, Wynn posted a cryptic scene from The Matrix to X, showing Neo stopping bullets mid-air — perhaps a nod to surviving chaos, or hoping to. Despite the massive loss, he still holds an open long, currently running at a significant unrealized loss.

Wynn first rose to prominence with huge returns from early bets on tokens like Pepe (PEPE), riding the memecoin wave to multi-million dollar profits. But his own words had always foreshadowed a potential downfall. In a post just before the liquidation, he described himself as “an extreme degenerate,” admitting his trades were more gambling than strategy.

“I don’t follow risk management,” he wrote. “I could lose everything — and I advise others not to do what I do.”

Alexander Stefanov

With over 8 years of experience in the cryptocurrency and blockchain industry, Alexander is a seasoned content creator and market analyst dedicated to making digital assets more accessible and understandable. He specializes in breaking down complex crypto trends, analyzing market movements, and producing insightful content aimed at educating both newcomers and seasoned investors. Alexander has built a reputation for delivering timely and accurate analysis, while keeping a close eye on regulatory developments, emerging technologies, and macroeconomic trends that shape the future of digital finance. His work is rooted in a passion for innovation and a firm belief that widespread education is key to accelerating global crypto adoption.