James Wynn, a high-profile cryptocurrency trader known for extreme leverage plays, was liquidated Friday on a $50 million Bitcoin (BTC) long position mere hours after reentering the market, according to blockchain analytics firm Arkham Intelligence.
Wynn, who had previously claimed he would step away from high-risk trading, opened the leveraged position on the decentralized perpetual futures platform Hyperliquid at 14:26 UTC. Bitcoin was trading near $109,146 at the time, leaving his position at break-even, according to Arkham’s shared candlestick data.
But within two hours, Bitcoin prices fell sharply. By 16:46 UTC, BTC dropped to $104,771—triggering the liquidation of Wynn’s entire position. The swift 4% drop wiped out his $50 million bet and reignited scrutiny of his aggressive trading style.
The loss quickly sparked reaction across crypto social media platform X. “Revenge trade gone wrong,” posted user @TiffanyEngr, while @CryptoVikings07 expressed disbelief. Arkham’s data also showed Wynn’s wallet, tagged “JamesWynnReal,” recording $90,000 in USDC inflows and outflows via the Hyperliquid Bridge earlier in the day, reflecting ongoing aggressive strategy despite past warnings.
This is not the first time Wynn has faced major setbacks. On May 26 that Wynn lost over $60 million in a single week. On May 19, he opened a 40x BTC long at $103,302 with a liquidation price of $98,294. After that, he pivoted to a massive short position on May 25, holding nearly 8,000 BTC valued at $856 million. That trade, too, was liquidated after a modest price reversal, underscoring the razor-thin margins of his high-leverage strategy.
Hyperliquid itself has been a hub for leveraged crypto activity. The platform surpassed $1 billion in USDC net inflows following the launch of its native token, Hype. Open interest reached a record $4.3 billion, highlighting growing participation—but also elevated systemic risk—on the platform.
While Wynn’s latest bet was focused on Bitcoin, the broader crypto market provided little support. Although Changelly issued a bullish short-term outlook for Bitcoin Cash (BCH) on May 29, Bitcoin exhibited pronounced volatility, with the sudden price decline likely exacerbated by options expiration timing, according to traders on X.
One user, @PiP_Quant, noted that the final Friday of the month—coinciding with options expiry—often results in erratic price action, making it a “terrible time” to place directional leveraged trades. Meanwhile, @Cryptorizz_ reported that Wynn had accused Arkham of misrepresenting his trades, though blockchain records appear to confirm Arkham’s timeline.
Wynn’s repeated losses highlight the risks of extreme leverage in crypto markets. While such strategies offer the potential for rapid gains, they often result in devastating drawdowns amid high volatility. For now, Wynn’s next move remains unclear—but his continued presence in the market will be closely watched.
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