Bitcoin Trader Loses Nearly $100 Million in Hyperliquid Long Bet Liquidation

James Wynn, a high-stakes trader on Hyperliquid, has suffered a near-$100 million loss after a series of leveraged long positions on Bitcoin were liquidated during a sudden market dip. Wynn, known for his aggressive trading strategies, saw his bold bets collapse on May 30 as Bitcoin’s price fell sharply below $105,000.

Nearly 1,000 BTC Liquidated in Hours

According to on-chain data from analytics platform Hypurrscan, two of Wynn’s largest positions were closed in quick succession. The first, a 527.29 BTC long valued at $55.3 million, was liquidated when Bitcoin dropped to $104,950. Moments later, another 421.8 BTC worth $43.9 million was wiped out as Bitcoin slid further to $104,150.

These losses came on the heels of another 94 BTC ($10 million) liquidation on May 29 at $106,330. In total, Wynn lost 949 BTC — equating to approximately $99.3 million. Data from Lookonchain confirmed Wynn’s total losses over the past week hover just below the $100 million mark.

Bitcoin reached to $105,000 on May 30, with some platforms reporting even deeper lows. Wynn’s positions were exposed to massive downside risk, as he had increased his 40x leveraged bet to $1.25 billion just days earlier, on May 24. 

That gamble backfired when the market reacted to geopolitical uncertainty and renewed tariff rhetoric from U.S. presidential candidate Donald Trump.

Wynn: “I Stand to Lose Everything”

Following the dramatic liquidations, Wynn responded on X with a cryptic screenshot from The Matrix showing Neo stopping bullets — a subtle nod to the pressure he faced. Despite the losses, one of Wynn’s massive positions remains open: a 40x leveraged long contract entered at $107,993. According to Hypurrscan, it is currently showing an unrealized loss of $3.4 million.

Wynn, who rose to fame after turning memecoin investments — particularly Pepe — into multi-million-dollar wins, appears unfazed by the volatility. A day before the liquidation, he described himself as an “extreme degenerate” and admitted to ignoring risk management.

“I do not follow proper risk management… I’m effectively gambling. And I stand to lose everything,” Wynn warned — a candid reflection of the high-risk world of crypto leverage trading.