James Wynn Faces Massive Loss as Bold Bitcoin Bet Backfires
Bitcoin Dip Wipes out James Wynn’s fortune as the prominent figure on the Hyperliquid platform suffers devastating losses nearing $100 million after Bitcoin’s price tumbled beneath the $105,000 mark. His bold approach to trading, which involved heavy leverage, left him exposed when the market turned against him.
Image 1: Bitcoin and Pepe (Source: NewsBTC)
Leveraged Gamble Backfires
Wynn placed long positions on Bitcoin, speculating that its price would continue climbing. He used 40 times leverage, a method that allows traders to control a large amount of value with a relatively small deposit. While this can lead to big profits, it also magnifies losses when the market goes in the opposite direction.
On 24 May, Wynn increased his leverage significantly, pushing his total position to approximately $1.25 billion at a Bitcoin price of around $107,993. Just days later, on 29 May, his first loss hit—94 BTC, worth around $10 million, was liquidated when Bitcoin dropped to $106,330. The following day, the downturn intensified. Bitcoin’s price fell even further, and two more major positions were closed.
According to Hypurrscan, a blockchain tracking tool, one of Wynn’s trades—527.29 BTC worth about $55.3 million—was liquidated when Bitcoin hit $104,950. Another position of 421.8 BTC, valued at $43.9 million, was cleared out after the asset fell to $104,150. These transactions resulted in a combined liquidation of 949 BTC. Analysis from Arkham Intelligence and Lookonchain suggests that Wynn lost close to $100 million in total during this week of trading.
Market data from TradingView revealed that Bitcoin fell to as low as $104,630 on Coinbase during early trading hours on 30 May. However, prices were even lower on some other exchanges. The fall in value followed renewed concerns over possible trade tariffs raised by US President Donald Trump, which appeared to rattle investor confidence and push crypto prices downward.
Still Holding a Risky Position
Despite the enormous loss, Wynn has not completely withdrawn from the market. Hypurrscan data indicates that his leveraged position remains open. The trade was entered when Bitcoin was trading near $107,993 and has already chalked up an unrealised loss of about $3.4 million. Though the position has not yet been liquidated, further price drops could trigger additional losses.
Wynn did not release a formal statement in response to the liquidation. Instead, he posted a symbolic image from The Matrix, featuring the main character in a moment of resistance. His social media activity during the episode has drawn attention for its emotional tone, with repeated calls for support and expressions of frustration.
Known for Risk, Not Caution
Wynn rose to popularity within the crypto community due to his early success with memecoins, particularly PEPE, which had brought him significant gains. However, his recent behaviour suggests a trading style that borders more on gambling than calculated investing.
On 29 May, prior to the worst of the losses, Wynn shared on social media that he engages in highly risky trades and admitted he does not follow standard risk management practices. He described his approach as relying more on luck than skill, and openly stated that his trading is extremely high-risk and could result in losing everything.
He also made it clear that his online activity was never intended as financial guidance. Instead, he framed his actions as entertainment and warned others not to attempt similar trades.
That same day, his posts became more emotional. In multiple updates, he appeared to express frustration with the outcome of his trades and possibly asked others in the crypto community for help. His tone was a mix of desperation and defiance, adding a dramatic flair to an already intense financial situation.
He wrote:
“TWO TIMES AND FAILED.
GIVE A MAN A FIGHTING CHANCE.
I’AM NOT YOUR ENEMY!
ENOUGH TO GO AROUND!”
Image 2: Hyperliquid whale loses $100 million (Source: TokenPost)
A Stark Reminder for Crypto Traders
Wynn’s story is a striking example of what can happen when high leverage is used without proper safeguards. Though the potential rewards may be tempting, the risks are just as large, if not greater. In this case, one of the most well-known traders on Hyperliquid saw his fortune drop nearly overnight.
Read Also: Analyst Predicts Bitcoin May Still Surge Past $300K This Cycle
While some may admire his daring, others in the industry have pointed out that his actions could mislead less experienced traders into believing such strategies are sustainable. With markets that move as quickly and unpredictably as crypto, even one bad week can erase years of gains.
For now, Wynn remains active in the market, but he is deeply in the red. Whether he will bounce back or face further losses remains to be seen. What is clear, however, is that the consequences of overleveraged trading can be both swift and severe, even for those who have previously enjoyed success.
