Prominent cryptocurrency trader James Wynn has announced his departure from perpetual contracts after leveraging an initial investment of $4 million to amass a staggering $100 million, only to ultimately face a collapse resulting in a $17.5 million deficit. However, blockchain data indicates that his trading activity is far from over.
Shortly after Wynn’s public exit from perpetual trading, on-chain analytics revealed he had initiated a new $100 million long position on Bitcoin, entering at $105,890.30 with a massive 40x leverage.
Source: Hypurrscan
$100M High, $117.5M Swing, and a Brutal Exit: James Wynn’s Wild BTC Ride
Wynn, known for his transparency in the cryptocurrency arena, attracted significant attention in May with a series of high-stakes Bitcoin trades.
Trader James Wynn is down millions, live on-chain. His trades shook crypto, but Hyperliquid is winning. Here’s what it all means. #JamesWynn #Hyperliquid #Bitcoin https://t.co/0zaR5Z0VyQ
— Finance Newso.com (@Finance Newso) May 28, 2025
On May 21, he opened a staggering $830 million long position on Bitcoin, later increasing it by another $1.1 billion as the cryptocurrency surpassed $111,000, leading to unrealized profits nearing $40 million. This position was set with a liquidation threshold of $107,975.
Despite initial success, complications arose when Bitcoin prices plummeted following former President Trump’s announcement regarding tariffs.
In an attempt to shield his investments, Wynn executed a $856 million short position on May 25, also at 40x leverage, but exited just 15 hours later incurring a loss of $15.5 million.
His final successful trade occurred on May 24, producing a profit of $18.4 million as part of his risk management strategy.
Unfortunately, on that same day, he liquidated a $1.25 billion long position on Hyperliquid, closing it at a $13.4 million loss despite having briefly observed $40 million in paper profits. He simultaneously concluded a sale of 540 BTC, securing a $1.5 million profit.
Overall, Wynn’s trading endeavors culminated in staggering swings totaling $117.5 million. One of his most significant exits came after Bitcoin fell to $107,431, narrowly avoiding his $104,000 liquidation level. He confirmed this exit on X, expressing that he had “cut his losses.” Previously, he had accrued $25.19 million from a PEPE long position.
The downturn marked the conclusion of an extraordinary journey, rising from $4 million to a portfolio peak of $100 million. Reflecting on the experience in a thread on X, Wynn described his final trading hours as “surreal,” admitting he had posted cryptic warnings as the market approached critical liquidation points.
I’ve decided to give perp trading a break.
Thank you @HyperliquidX for your hospitality. Your service, impeccable. Your platform exquisite.
It’s been a fun ride. Approx $4 million into $100 million and then back down to a total account loss of $17,500,000.
The time has come for me to…
— James Wynn (@JamesWynnReal) June 2, 2025
Wynn attributed his financial struggles to real-time funding costs incurred on Hyperliquid, stating that the toll was “not just emotional” but also had a tangible impact: “bleeding by the second.”
Despite claiming he would take a step back, blockchain evidence from Hypurrscan showed he reopened with a new $100 million Bitcoin long on Hyperliquid just hours later, again leveraging 40x and entering at $105,890.30.
As of the latest updates, his new position has already experienced a downturn of $1.7 million, and Wynn seems to be adding to it to stave off liquidation.
Source: Hypurrscan
Community Split as Whales Fade, Retail Follows
Wynn’s rapid return to the market with another large 40x leveraged long position has polarized the cryptocurrency community. His current position, now the largest on Hyperliquid, has reignited discussions surrounding decentralized exchanges (DEXs). While some view his transparency favorably, others criticize it as reckless.
An AI crypto assistant on X characterized Wynn’s actions as “textbook degen,” highlighting that certain whales are actively shorting against his trades while retail investors appear to be following his lead.
Furthermore, analyst Alva raised alarms over troubling technical indicators, such as a CRSI above 92 and a bearish MACD cross, suggesting further potential declines. “Wynn’s straight back in with size,” Alva cautioned.
Wynn’s latest BTC actions are textbook degen: after catastrophic losses, he’s straight back in with another massive long, drawing both copiers and contrarians.
On-chain data shows major whales fading his entries, while retail piles in—social sentiment is split, with fear of…
— Alva (@AlvaApp) June 2, 2025
In the midst of Wynn’s tumultuous trades, some unexpected beneficiaries have emerged. A trader utilizing the wallet address 0x2258 reportedly garnered $5.6 million in just three days by strategically counter-trading Wynn’s public positions.
A trader has racked up $5.6 million in profits in just three days by systematically betting against the trades of prominent crypto figure @JamesWynnReal. #Trader #Bitcoin https://t.co/r2KVFOSy4Y
— Finance Newso.com (@Finance Newso) May 27, 2025
Beginning on May 24, 0x2258 initiated short positions on BTC and ETH as Wynn entered a long position. When Wynn subsequently exited his position the following day, this trader closed their short for a profit of $1.36 million, showcasing a pattern of well-timed trading that has caught attention throughout the cryptocurrency markets.
The post Crypto Trader James Wynn Quits Perps After $100M Rollercoaster—Now Bets $100M on BTC: Can He Rebound? appeared first on Finance Newso.
