James Wynn is the millionaire trader who is now infamous for being liquidated of nearly $25 million in Bitcoin after betting $1.25 billion with leverage that the flagship cryptocurrency’s price would rise.
Blockchain analytics platform Lookonchain shared in an X post on June 4 that Wynn lost 240 BTC and had manually closed part of his position to lower the trade’s liquidation price. Data from Hypurrscan shows that the trader is currently sitting on an unrealized loss of nearly $1 million on a 40x Bitcoin long position.
The trader rose to prominence after making a series of large, high-leverage bets on Bitcoin and memecoins through the decentralized trading platform Hyperliquid. The history of his position is publicly available on the platform. Wynn experienced one of the steepest losses in crypto trading. In just a week, he managed to lose more than $60 million.
Let’s take a look at the timeline of his unfortunate Bitcoin bet and the story of the madman who was willing to put his entire wealth on the line to become a billionaire trader.
Who is James Wynn?
James Wynn made his debut in the crypto trading world in early 2022, the final phase of the 2021 bull market that saw Bitcoin and other major cryptocurrencies register their all-time highs. He was reportedly paid $6,000 in Ether (ETH) by Alameda Research, the now-defunct crypto market maker and investment firm tied to Sam Bankman-Fried, which was known at the time for backing emerging traders.
However, his first major move wasn’t until a few years later when he made a $7,000 investment in the Pepe the Frog (PEPE). At the time, the memecoin’s market cap stood at just $600,000, but soon after, its valuation grew to $4.2 million, and Wynn’s aggressive trading methods helped him turn the initial investment into a $25 million profit.
Following his success with memecoins, he shifted his focus to leveraged trading and joined Hyperliquid. Wynn came back into the picture in March 2025, when he began trading on the trading platform with $4.65 million in USD Coin (USDC). Over a two-month period, he executed 38 trades on the exchange, primarily focusing on BTC and memecoins such as PEPE, TRUMP, and FARTCOIN, out of which 17 of them resulted in profits.
In early May, reports showed that the trader had turned his positions into a $46.5 million profit, with the amount peaking at $87 million on May 23.
His long position in PEPE generated $25.19 million, followed by BTC with $16.89 million, a long trade in TRUMP yielding $6.83 million, and a similar position in FARTCOIN that earned him $4.84 million. Hyperliquid also benefited from his activity, with Wynn paying the exchange approximately $2.13 million in trading fees.
James Wynn’s Leverage Trading Playbook
He employs a unique trading strategy, blending high leverage with fast execution and sensitivity to market conditions and investor sentiment. Wynn typically operates with leverage that ranges from 5x to 40x, and builds positions in fast-moving cryptocurrencies that exhibit strong momentum.
Trade size is another defining aspect of his approach, where the bets carry notional values in millions. While it creates significant market exposure, it increases vulnerability tremendously. His liquidation threshold tends to sit within a narrow 2-3% range below the entry price, which means that even a minor drop could result in him suffering massive losses within minutes.
His trading playbook also integrates social media, as he regularly shares his positions and provides real-time updates on X. He uses transparency to build credibility while influencing market psychology. Wynn’s social media presence can potentially amplify trends that are already in motion, adding another layer of strategy to his trading method.
How Does Leveraged Trading in Crypto Work?
Leverage trading allows crypto traders to amplify their positions well beyond their actual capital. The method is often used by high-leverage traders, like James Wynn, to maximize the returns on their initial investments. While leverage trading creates the possibility of making large gains, traders are also at the risk of suffering sharp and fast losses.
Typically, a trader opens a position by depositing a fraction of the total value required, known as the margin. They then borrow the remaining amount needed to reach their desired leverage ratio. The trader then executes the trade, and the borrowed funds are used to amplify the potential gains or losses. If the trade is a loss, then their position may be liquidated, resulting in a loss of the borrowed funds and also the margin.
Let’s take an example to better understand this trading strategy. Assume that a trader wants to buy $100,000 worth of Bitcoin with a 10x leverage ratio, then their margin will be $10,000 (10%) of the total position, with borrowed funds making up 90% of the composition.
If BTC price increases by 10%, then the trader’s profit would be $10,000, representing 10% of the $100,000 position. However, the trader could experience a significant loss of the borrowed funds and potentially the margin if Bitcoin’s price decreased by 10%, pushing their losses to $90,000, amounting to 90% of the total position.
Exchanges like Hyperliquid, Binance, Bitget, and Bybit provide traders with leverage levels ranging from 5x to 100x, depending on the asset they choose and the platform’s policies. While it offers flexibility and capital efficiency, it also has a small margin for error that can result in forced liquidations within minutes.
Trading platforms often apply additional buffers, known as maintenance margins, which may trigger liquidation slightly before the full margin is lost. This is to ensure system solvency and protect insurance funds.
James Wynn’s $1.25 Billion Bitcoin Leveraged Trading Sequence
Wynn began his bet on May 19 by opening a 5,520 BTC long position with a 40x leverage. At the time, Bitcoin was priced at $103,302, placing its liquidation level at $98,294. The very next day, he raised his position to 7,764 BTC, increasing the notional value of his position to $830 million. This moved his average entry point to $105,033, setting the liquidation at $100,330, further narrowing the buffer between market price and liquidation.
On May 21, Bitcoin’s price gained momentum, which led to Wynn increasing his position to 9,371.71 BTC. This pushed the bet above the $1 billion mark, making it the largest ever. At that point, his trade was in profit, showing unrealized gains of $10.71 million at an average entry of $108,005.
Fueled by the prospect of Bitcoin targeting a new ATH, Wynn closed a short position of 2,138 BTC, which secured him $11.92 million in realized profit, but left 5,203 BTC worth nearly $555 million still active. He followed it up by opening a new long on May 22 with 10,200 BTC, priced at $108,065. When Bitcoin recorded its new peak close to $112,000, the trader’s unrealized profits stood at $39 million.
However, the positive momentum didn’t last long. On May 23, Bitcoin suffered a 4% drop to $106,700 after US President Donald Trump threatened a 50% tariff on European imports. Wynn responded by closing a separate position he had with PEPE, which made him a $25.18 million profit. On May 24, he used the proceeds to raise his Bitcoin long to 11,588 BTC at $108,243, worth $1.25 billion, with 40x leverage, setting the liquidation level at $105,180.
But this decision proved costly as the following day, he exited at $107,746, booking a $13.39 million loss. That same day, he increased his Bitcoin short position to 7,967.83 BTC, valued at $856 million, with a liquidation price set at $111,280. However, 15 hours later, on May 26, he exited over $1 billion worth of BTC short positions, suffering a loss of approximately $15.87 million.
Wynn also closed his long positions in ETH and SUI, which cost him an additional $5.3 million in losses. He also lost $976,635 on a long Bitcoin trade and a 10x leveraged long position in PEPE that resulted in a loss of $858,580. The total drawdown over the seven days reached $60 million.
In a May 26 post, he finally acknowledged the setback, but noted that despite the losses, he still held a $25 million profit from an original base position of $3-4 million. But this figure marked a sharp drop from his earlier peak of $87 million.
On May 29, Lookonchain and Arkham Intelligence reported that Wynn suffered a loss of $100 million over the course of the week. Unfazed by the losses and fueled by his drive to make a billion dollars in profit, the trader initiated a second $100 million leveraged position on Bitcoin. But things didn’t last long, as he was liquidated for the remaining 770 BTC, worth around $80.5 million, at a liquidation price set at $104,035. This led to Wynn losing the $25 million profit he was originally holding.
Data also showed that the trader suffered an unrealized loss of nearly $1 million on his 40x Bitcoin long position. Following the liquidation, Wynn took to X, alleging that the market was manipulated against him, seeking donations to expose the conspiracy.
Accusations Against Wynn
The trader has faced heavy criticism over his promotional activities, particularly involving low-cap cryptocurrencies. Wynn had promoted tokens like ELON and WYNN, which collapsed quickly upon launch. He was also alleged to have received 2% of the Baby Pepe token supply from the team as part of his marketing efforts, only to quickly sell all his tokens and take profit.
He was also tied to the controversy surrounding the Solana-based MOONPIG memecoin, for which he is accused of buying 3% of the total supply to pump its price to an all-time high. He later sold off his shares, which some claim caused MOONPIG’s price to collapse dramatically.
Despite these accusations, he denies any wrongdoing and claims to be only an investor and not involved in the development of market-making for any cryptocurrency project.
Also Read: Andreas Antonopoulos: The Veteran In Blockchain Technologies
Final Thoughts
Following Wynn’s $100 million liquidation, Binance co-founder and former CEO Changpeng “CZ” Zhao proposed the idea of a dark pool perpetual swap decentralized exchange (DEX) that he claims could potentially counter market manipulation tactics.
The whale, who was once celebrated as a visionary, now faces serious questions about his trading methods and decisions in a market that does not forgive missteps. As the crypto market moves ahead, enthusiasts are closely watching Wynn’s next moves.
