After $100M Liquidation, James Wynn’s New Bitcoin Position Turns Heads on Hyperliquid

Key Insights:

• Wynn’s $99M BTC long was liquidated on May 30.
• He sold $4.1M in HYPE tokens for USDC, gaining $1M.
• Reentered with a new 40× BTC long, now down 73%.
• Known for high-leverage trades and extreme risk.

After losing nearly $100 million on a high-leverage Bitcoin trade, crypto trader James Wynn returned to the market with another aggressive bet—this time following a $4.1 million stablecoin cash-out from Hyperliquid’s governance token, HYPE.

$100 Million Bitcoin Long Liquidated on Hyperliquid

James Wynn’s BTC long position, worth approximately 949 BTC (about $99.3 million) on Hyperliquid, was fully liquidated on May 30, as Bitcoin dipped below $105,000. The trades were placed using 40× leverage, leaving almost no room for error.

According to Arkham Intelligence, Wynn held 527.3 BTC and 421.8 BTC long at the time of liquidation. The collapse represented one of the largest losses in the perpetual futures market this year. Analysts noted the liquidation as a significant event, citing the extremely tight margin on such large positions.

HyperDash, a blockchain analytics tool, tracked a nearly $81.45 million drop in Wynn’s account equity over the final week of May.

Shortly after the liquidation, Wynn moved to cash out his HYPE token holdings. On-chain data from Spot On Chain confirmed that he unstaked and sold 126,116 HYPE tokens, converting them into $4.12 million USDC at an average price of $32.70.

He had previously accumulated the tokens at $24.40, netting an estimated $1.05 million profit on the trade. He then withdrew the USDC to his personal wallet, a move widely interpreted as taking stablecoin risk off the table—briefly.

Arkham flagged the transaction in real-time, noting, “James Wynn unstacked and sold $4.1M of HYPE for USDC, then went straight back to the casino.”

James Wynn Re-Entry: Another 40× BTC Long

Wynn’s withdrawal didn’t last long. He re-entered the market with another 40× leveraged BTC long, reportedly worth approximately 945 BTC. Within minutes, the position showed a –$1.18 million unrealized loss.

By late May, his Hyperliquid account was down 12 million overall, with return-on-equity (ROE) plunging –70%, based on analytics from HyperDash. Arkham stated Wynn was “currently down 73%” on the new position.

Wynn is no stranger to volatility. In 2022, he turned $7,000 into $25 million trading meme tokens like PEPE. This year, he returned to active trading on Hyperliquid, starting with $4.65 million USDC in March.

He quickly grew that balance to $46.5 million by mid-May through high-leverage bets, mostly on Bitcoin and meme coins like PEPE, FARTCOIN, and Official Trump.

His trading style favors extreme leverage (5–40×) with narrow liquidation margins. The risk is often binary. In one tweet on May 31, Wynn commented: “Flipping $4m to $100m and back down to -$13m is one hell of a thrill.”

Traders Watch—and Counter—His Moves

Some traders have started shadowing Wynn’s trades—but in reverse. Lookonchain reported one wallet earning $17 million by consistently taking the opposite side of Wynn’s positions.

Market watchers have also raised concerns over potential manipulation. On May 30, a rapid BTC price drop appeared to coincide precisely with Wynn’s liquidation. The sentiment of the moment: “This looks like manipulation!” some traders wrote, suspecting bot-driven triggers.

James Wynn’s rapid-fire trades remain a spectacle in crypto circles. He’s a case study in high-risk, high-volatility strategy—willing to ride extreme positions up or down.

The real-time visibility of his trades, enabled by Arkham and HyperDash, ensures the crypto world keeps watching—whether to learn, bet, or countertrade.

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