James Wynn's Bitcoin trade spirals into a $60M wipeout

James Wynn, a well-known high-leverage crypto trader, recently experienced one of the steepest losses of his career.

What happens when Bitcoin doesn't follow the script, and a trader like James Wynn is already deep into a leveraged bet he can't easily escape?

One of the steepest losses in recent memory has hit high-leverage crypto trader James Wynn, also known as "HYPER,") is known for his massive positions and rapid-fire trades on the Hyperliquid (HYPE) exchange.

Over seven days, Wynn's trades resulted in an estimated $60 million drawdown, largely driven by a series of leveraged Bitcoin (BTC) positions that went sour as the market shifted and triggered liquidations.

The sequence began on May 19 with a 5,520 BTC at $103,302, leveraged 40x and setting his liquidation level at $98,294.

The following day, he expanded the position to 7,764 BTC, raising the notional value to $830 million and setting his new average entry at $105,033 for a closer buffer to the liquidation price of $100,330.

May 21 saw him increase exposure further to 9,371.71 BTC, pushing the position above the $1 billion threshold at an average entry of $108,005 and showing a $10.71 million profit.

Later that day, Wynn closed 2,139 BTC, securing $11.92 million in realized profit, leaving 5,203 BTC still active, valued at $554.6 million.

He followed up with a fresh long of 10,200 BTC at $108,065, which brought the Bitcoin position above $5 billion in notional at its peak as the cryptocurrency touched $111,900, pushing unrealized gains to $39 million.

But momentum reversed quickly. On May 23, a 4% drop brought Bitcoin down to $106,700 following President Trump's announcement of a 50% tariff on European Union imports.

Wynn responded by closing a separate Pepecoin (PEPE) position with a $25.18 million gain and raising his Bitcoin long to 11,588 BTC at $108,243, setting his new liquidation level at $105,180.

That decision proved costly. On May 25, he exited the position at $107,746, booking a $13.39 million loss.

That same morning, he shifted to a short strategy, scaling his Bitcoin position to 7,967.83 BTC, valued at $856 million, with a liquidation price set at $111,280.

HYPER is known for his bold trading style, which involves high leverage and aiming for substantial gains or swift losses.

He later exited over $1 billion worth of BTC short positions on May 26, incurring a loss of approximately $15.87 million over a 15-hour span.

He also closed his Ethereum (ETH) and Sui (SUI) longs during the week, incurring an additional loss of $5.3 million.

The total drawdown over seven days amounted to about $60 million.

Wynn acknowledged the setback in a post on May 26, where he stated that despite the losses, his account still held $25 million in profit from an original base of $3–4 million. The figure represented a sharp drop from his earlier peak of $87 million.

"Lost around $60 mil in the past week for those keeping score. Still up $25 mil from where I started (3-4 mil) and have about 3-4 bil in volume on HYPE in the past 3 months."

What makes James Wynn trader different from the average degen

Wynn began gaining traction in the crypto trading world in 2022, during the final phase of the previous bull market. His early entry into the space was reportedly funded by Alameda Research, a firm known at the time for backing emerging crypto traders.

That year, he invested $7,000 into the memecoin PEPE when its market cap was just $600,000. As the token’s valuation rose to $4.2 million, Wynn employed high-frequency trading methods to eventually turn his position into $25 million.

In March 2025, Wynn began trading on Hyperliquid, starting with a deposit of $4.65 million in USD Coin (USDC). Over the following two months, he executed 38 trades on the platform, focusing primarily on Bitcoin and memecoins such as PEPE, Official Trump (TRUMP),