High-Stakes Leverage Trader Who Made and Lost $100M Is Back and He’s Long on These 3 Cryptos

Key Takeaways

• James Wynn previously made nearly $100 million trading perpetual futures, only to lose it all.

• After taking a hiatus, Wynn returned to Hyperliquid on Wednesday with a $197,000 USDC.

• True to form, he immediately placed a series of high-leverage long bets on three cryptocurrencies.

Earlier this year, James Wynn, a crypto trader known for high-risk, high-reward leverage trades, announced that he was quitting perpetual futures after a string of multi-million dollar liquidations.

But on Wednesday, Oct. 15, Wynn deposited around $197,000 USDC on Hyperliquid and was immediately back to his old ways, opening long positions with 10–40x leverage on BTC, ETH, and PEPE.

Wynn first rose to prominence in 2023, when he turned a $7,600 PEPE investment into $25 million.

He subsequently built a following on X by posting about memecoins and sharing his high-stakes leverage trades, characterized by multimillion-dollar positions and nail-biting swings between profit and loss.

After he started trading perpetual futures on Hyperliquid in March 2025, followers could watch Wynn’s rollercoaster crypto bets play out in real time. He opened the account with just a few million dollars and quickly racked up $87 million in profit making bold bets with up to 40x leverage.

At one point during this period, Wynn held long positions on Bitcoin worth $1.25 billion. But his luck ran out when the crypto market turned bearish, and a cascade of liquidations erased his gains.

By his own account, Wynn’s Hyperliquid adventure ended with $13 million in losses. Announcing his intention to retire from perp trading at the end of May, he said “the perps casino was fun,” and that he had “zero regrets.”

Despite indicating that he was done with perpetual futures, Wynn continued to make small trades, including some on the Hyperliquid rival, Aster.

On Oct.15, Wynn announced he was “back with a vengeance, coming to get what’s rightly mine.”

Shortly after depositing nearly $200,000 of Hyperliquid, Wynn had opened positions including 40x cross-margin Bitcoin longs valued at $3.8 million. Other bets include long ETH and PEPE contract with cross-margin leverage of 25x and 10x respectively.

At the time of writing, all three are in red, but there is still ample room for the market to drop further before they are liquidated.

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