Hyperliquid Whale James Wynn Suffers Nearly $100M Loss After Bitcoin Slips Below $105K

A prominent trader on the Hyperliquid exchange, James Wynn, has taken massive losses totaling nearly $100 million after Bitcoin’s price dipped below the critical $105,000 mark.

Wynn, known for his high-risk leveraged bets, saw his 949 Bitcoin long positions liquidated on May 30, marking one of the largest individual wipeouts in recent memory.

Massive Long Positions Liquidated

According to data from Hyperliquid’s analytics platform Hypurrscan, Wynn had two major leveraged long positions open:

• 527.29 BTC ($55.3 million), liquidated when Bitcoin hit $104,950

• 421.8 BTC ($43.9 million), liquidated as Bitcoin dropped further to $104,150

These liquidations came after an earlier hit on May 29, when Wynn’s 94 BTC ($10 million) position was wiped out at $106,330.

In total, across these three positions, Wynn lost 949 BTC, translating to a staggering $99.3 million in liquidations over just a few days.

James Wynn liquidation transactions. Source: Arkham Intelligence

Bitcoin Price Dip Sparks Cascade

Bitcoin’s price wicked down to $104,630 on Coinbase during early trading hours on May 30, according to TradingView. On other exchanges, the drop was even steeper. This sudden dip, partially driven by renewed tariff talk from U.S. President Donald Trump, set off a cascade of liquidations for high-leverage traders like Wynn.

Notably, Wynn had amplified his exposure on May 24 by increasing his 40x leveraged Bitcoin long position to a jaw-dropping $1.25 billion — a massive bet that the market would continue rising.

Wynn’s Response: A Cryptic Message

In response to the wipeout, Wynn posted a cryptic image on X (formerly Twitter): a still from the 1999 sci-fi classic The Matrix, showing Keanu Reeves’ character Neo stopping bullets in midair — perhaps signaling defiance or hope for recovery.

Interestingly, Wynn still maintains his 40x leveraged long position via a perpetual contract, opened when Bitcoin was at $107,993. As of now, this position is sitting on an unrealized loss of $3.4 million, according to Hypurrscan.

Source: Hypurrsan

“Extreme Degenerate” Trading Style

Wynn first gained notoriety for his memecoin plays, particularly his investments in Pepe (PEPE), where he reportedly made millions.

However, Wynn himself admits to being a high-risk gambler rather than a disciplined trader. In a statement on May 29, before the large liquidations hit, he described himself as an “extreme degenerate” engaging in reckless leverage:

“I do not follow proper risk management, nor do I claim to be a professional; if anything, I claim to be lucky. I’m effectively gambling. And I stand to lose everything. I strongly advise people against what I’m doing!”

The Bigger Picture

Wynn’s story is a cautionary tale in the crypto space, where high leverage can lead to rapid gains but equally rapid destruction. As Bitcoin’s price continues to fluctuate wildly near all-time highs, traders — especially retail participants — would do well to remember the brutal lessons of risk management.

Whether Wynn can recover from these eye-watering losses or if this marks the end of his legendary run remains to be seen.