James Wynn, the high-profile trader who recently went viral for placing a $1 billion Bitcoin long on decentralized exchange Hyperliquid, has suffered a catastrophic $99.3 million loss after Bitcoin’s price unexpectedly dipped below $105,000. The liquidation is one of the largest ever recorded on the platform and underscores the harsh risks of leveraged trading in volatile markets.
According to Hypurrscan data, Wynn opened two massive long positions—527.29 BTC and 421.8 BTC—wagering on continued Bitcoin momentum. Both positions were forcibly liquidated as BTC fell to $104,950 and $104,150, respectively. A third position—94 BTC—was already wiped out the previous day at $106,330, bringing Wynn’s total loss over a 48-hour period to 949 BTC, worth nearly $100 million.
Analytics platforms including Arkham Intelligence and Lookonchain confirmed the scale of the loss, calling it a major cautionary tale in a market that’s increasingly populated by risk-tolerant traders betting on extreme price swings.
Wynn’s $1.25B Bitcoin Bet Collapses Amid Market Jitters
Bitcoin’s early morning slide on May 30 set off a wave of liquidations across derivatives markets, dragging down some of the largest open positions—including Wynn’s billion-dollar bet. While Bitcoin touched $104,630 on Coinbase, lower quotes on other exchanges exacerbated margin calls and left overleveraged traders scrambling.
Wynn had dramatically increased his exposure just six days earlier, upping his leverage to 40x and bringing the size of his position to $1.25 billion as Bitcoin hovered near $108,000. That confidence was short-lived. A sudden shift in macro sentiment—fueled by Donald Trump’s renewed tariff threats—triggered a broader sell-off that quickly flipped Wynn’s positions underwater.
Despite the massive realized losses, Wynn’s trading saga isn’t over. Hypurrscan data shows he still holds an active 40x long perpetual contract, entered at $107,993. That position is now nursing an unrealized loss of approximately $3.4 million.
In response to the chaos, Wynn broke his silence with a cryptic post on X, featuring an image of Neo from The Matrix stopping bullets mid-air—possibly signaling mental resilience or stubborn defiance in the face of ruin.
From Memecoin Fame to Margin Mayhem
James Wynn isn’t new to risk—or fame. His trading reputation was built on early wins in the memecoin market, particularly a legendary flip on PEPE, the frog-themed token that earned him millions and a loyal following on Crypto X. His fearless style attracted both admiration and concern, with many labeling him a “degen” for his refusal to follow traditional strategies.
But Wynn wasn’t pretending to be a disciplined investor. Just a day before his liquidation, he openly admitted to his reckless approach in a now-viral X post:
“I do not follow proper risk management. I’m effectively gambling. And I stand to lose everything. I strongly advise people against what I’m doing.”
Those words, once brushed off as bravado, now read as a sobering prophecy. Wynn’s losses are not just financial—they may reshape his identity in the trading world, from crypto icon to cautionary example.
Quick Facts
- James Wynn, a prominent Hyperliquid trader, has lost $99.3 million due to a major Bitcoin price dip.
- His positions—totaling 949 BTC—were liquidated after BTC dropped below $105,000.
- Wynn still holds a 40x leveraged long position initiated at $107,993, currently $3.4 million underwater.
- A self-proclaimed “degenerate,” Wynn previously warned followers that he ignored all risk management strategies.
- The downturn follows Trump’s tariff comments, which triggered broad market volatility.
