James Wynn is a billionaire trader and is notorious for liquidating nearly $25 million in Bitcoin after betting $1.25 billion on rising leverage of flagship cryptocurrency.
Blockchain analytics platform LookonChain was shared on the X Post on June 4th, with Wynn losing 240 BTC and manually shutting down some of his position to lower the trade liquidation price. Data from Hypurrscan shows traders are currently sitting at an unrealized loss of nearly $1 million in a 40x long position in Bitcoin.
Traders have become prominent after placing a series of large, highly leveraged bets on Bitcoin and Memcoin via the decentralized trading platform hyperliquid. The history of his position is published on the platform. Wynn experienced one of the steepest losses in crypto transactions. In just a week, he managed to lose more than $60 million.
Let’s take a look at his unfortunate Bitcoin bet timeline and the story of a 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 world of crypto trading in early 2022. This is the final stage of the bull market in 2021, when Bitcoin and other major cryptocurrencies hit record highs. He reportedly paid $6,000 from Alameda Research, the now-deprecated crypto market maker and investment company, tied to Sam Bankman Freed, known for supporting emerging traders.
But his first big move wasn’t until a few years later when he invested $7,000 in Pepe the Frog (Pepe). At the time, Memecoin had a market capitalization of just $600,000, but its valuation soon increased to $4.2 million, and Wynn’s aggressive trading methods helped turn the initial investment into a profit of $25 million.
Following his success with Memecoins, he shifted his focus to leveraged trading and joined Hyperliquid. Wynn returned to the photos in March 2025. He began trading on the trading platform for $4.65 million USD coins (USDC). For two months he ran 38 transactions in exchanges, focusing primarily on BTC and Memecoin such as Pepe, Trump and Fartcoin, of which 17 were profitable.
In early May, reports showed that traders changed their positions to $46.5 million in profits, peaking on May 23rd at $87 million.
His long position at Pepe produced $2,519 million, followed by BTC of $16.89 million, Trump’s long trade of $6.83 million, and a similar position at Fartcoin earned $4.84 million. Hyperliquid also benefited from his activities, with Wynn paying an exchange of about $2.13 million in trading fees.
James Wynn’s Leverage Trading Playbook
He employs a unique trading strategy, combining high leverage with market conditions and quick execution and sensitivity to investors’ sentiment. Wynn usually operates with leverage ranging from 5x to 40x, building a rapidly moving cryptocurrency position that exhibits strong momentum.
Trade scale is another critical aspect of his approach, with bets having conceptual value in millions. It exposes you to a large market, but greatly increases vulnerability. His liquidation threshold tends to sit within the 2-3% range, which is narrower than the entry price. This means that even a small reduction can result in a large loss within minutes.
His trading playbook also integrates social media. He regularly shares his position and provides real-time updates for X. He uses transparency to build reliability while impacting market psychology. Wynn’s social media presence could amplify a trend that is already moving, adding another layer of strategy to his trading methods.
How do crypto-levered transactions work?
Leveraged trading allows crypto traders to amplify their positions well beyond their actual capital. This method is often the case that a high leverage trader like James Wynn maximizes the return on his initial investment. Leveraged trading creates the possibility of making big profits, but traders also risk suffering from rapid and fast losses.
Typically, traders open up positions by depositing a portion of the required total amount known as margins. After that, borrow the remaining amount needed to reach the desired leverage ratio. The trader then executes the trade and the borrowed funds are used to amplify potential profits or losses. If trade is a loss, their positions can be liquidated and result in losses of borrowed funds and margins.
To better understand this trading strategy, let’s take an example. Assume that a trader wants to purchase $100,000 worth of Bitcoin at a 10x leverage ratio, and that margin is $10,000 (10%) of the total position, with borrowed funds accounting for 90% of the composition.
If the price of BTC rises by 10%, the trader’s profits will be $10,000, accounting for 10% of the $100,000 position. However, if the price of Bitcoin falls by 10%, traders could experience significant losses and potential margins in borrowed funds, pushing the losses to $90,000, reaching 90% of their total position.
Exchanges such as Hyperliquid, Binance, Bitet, Bybit will provide traders with leverage levels of 5x to 100x, depending on the policy of the assets and platform of choice. It offers flexibility and capital efficiency, but also has a slight margin of errors that can result in forced liquidation within minutes.
In many cases, trading platforms apply an additional buffer called maintenance margins. This can trigger a clearing slightly before the full margin is lost. This is to ensure the solvency of the system and protect the insurance fund.
James Wynn’s $1.25 billion Bitcoin Leveraged Trading Sequence
Wynn began betting on May 19 by opening a long position of 5,520 BTC with 40x leverage. At the time, Bitcoin was priced at $103,302, bringing its liquidation level to $98,294. The next day he raised his position to 7,764 BTC, increasing his position’s expected value to $830 million. This brought his average entry point to $105,033, bringing the liquidation to $100,330, further narrowing the buffer between market price and liquidation.
On May 21, Bitcoin prices gained momentum, with Winn increasing his position to 9,371.71 BTC. This pushed the bet over $1 billion, making it the biggest ever. At that point, his deal was profitable, showing an unrealized profit of $10.71 million with an entry average of $108,005.
Boasted by the prospect of Bitcoin targeting the new ATH, Winn closed its short position of 2,138 BTC. He followed that up on May 22nd, opening a new long at a price of $108,065 at 10,200 BTC. Traders’ unrealized profits were $39 million when Bitcoin recorded a new peak of nearly $112,000.
However, the positive momentum did not last long. On May 23, Bitcoin fell 4% to $106,700 after US President Donald Trump threatened a 50% tariff on European imports. Winn responded by closing out another position he had at Pepe, earning $25.18 million. On May 24, he used his earnings to raise Bitcoin to $108,243 to $11,588 BTC, with 40x leverage worth $1.25 billion, and set the liquidation level at $105,180.
However, the decision was costly the next day, and he ended at $107,746 and booked a loss of $13.39 million. On the same day, he increased his short Bitcoin position to 7,967.83 BTC, valued at $856 million, and the liquidation price was set at $111,280. However, 15 hours later, on May 26, he ended his BTC short position of over $1 billion, resulting in a loss of about $15.87 million.
Wynn also closed long positions at ETH and SUI. He also lost $976,635 in long Bitcoin trading and a long position that was 10 times leveraged at Pepe, resulting in a loss of $858,580. The total drawdown over the seven days reached $60 million.
In a post on May 26th, he finally admitted the set-off, but noted that despite the loss, he still holds a profit of $25 million from his original base position of $3-4 million. However, the figure showed a sharp drop from his previous $87 million peak.
On May 29, Lookonchain and Arkham Intelligence reported that Wynn suffered a loss of $100 million a week. Boasted by his drive to lose money and earn $1 billion, the trader launched his second $100 million leverage position in Bitcoin. However, things didn’t last long as he was liquidated for the remaining 770 BTC and set at $104,035 with a liquidation price worth around $80.5 million. This left Wynn losing the $25 million profit he originally held.
Data also showed traders suffered nearly $1 million unrealized losses in a 40x long Bitcoin position. After the liquidation, Wynn took over X, claiming that the market had been manipulated against him and sought a donation to expose the plot.
Accusations against Wynn
Traders have faced heavy criticism of his promotional activities, particularly those that include low-cap cryptocurrencies. Wynn was promoting tokens like Elon and Wynn. He was also said to have received 2% of the supply of Baby Pepe tokens from his team as part of his marketing efforts, but he will only sell all his tokens quickly and make a profit.
He was also involved in the controversy over Solana-based MoonPig Memecoin. He later sold the shares.
Despite these accusations, he denied fraud and claimed he was only an investor and not involved in the market production of cryptocurrency projects.
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Final thoughts
Following Wynn’s $100 million liquidation, Binance co-founder and former CEO Changpeng “CZ” Zhao has proposed the idea of a permanent swap distributed exchange (DEX) for Dark Pool, which he claims could counter market manipulation tactics.
Once celebrated as a visionary, the whale is now facing serious questions about how he trades and decisions in a market that does not allow for failure. As the crypto market moves ahead, enthusiasts are watching Winn’s next move closely.
