Bitcoin Slips, Wynn Crashes: A $99M Loss and the Crypto Trader Who Beat Him

TLDR:

• Bitcoin dropped below $105K, triggering massive liquidations across crypto markets
• James Wynn lost $99M after flipping from long to short positions during market dips
• Trader 0x2258 earned $17M by betting against Wynn’s high-leverage positions
• Wynn still holds $178M in BTC, with liquidation near $104,610 if prices fall again

Bitcoin slid below $105,000 early Thursday, triggering widespread liquidations and heavy losses for high-leverage crypto traders. 

Among the hardest hit was James Wynn, a crypto figure who recently gained fame for turning zero into millions within weeks. His rapid rise ended abruptly with a seven-day collapse that erased $99 million. 

As the market retraced, another trader quietly profited by taking the opposite side of Wynn’s bets. The contrasting outcomes reveal the high stakes and volatility now defining the crypto price action.

Crypto Trader James Wynn’s $83 Million Rise Ends in Collapse

Between March 20 and May 23, James Wynn transformed a starting balance of $0 into $83 million. 

Spot On Chain reported that he gained from leveraged long positions across several tokens, including PEPE and TRUMP. At the height of his run, Wynn held a $1.14 billion long position in Bitcoin, which showed a $39 million unrealized profit on May 22.

James Wynn (@JamesWynnReal) went from a record-breaking +$83M profit to a crushing -$12M loss in just 7 days. Here’s his journey. (1/4 🧵👇) pic.twitter.com/nfHzJ1H8dF

— Spot On Chain (@spotonchain) May 30, 2025

However, the winning streak reversed sharply. By May 24, Wynn had increased his Bitcoin exposure to $1.25 billion, only to see it dip into a $13.4 million loss within hours. A day later, he flipped bearish, placing $1 billion in shorts; this move backfired, resulting in a $15.87 million loss in less than 24 hours.

On May 30, Wynn’s positions were again hit as Bitcoin slipped under $105,000. He was liquidated for 949 BTC, amounting to $99.3 million in losses. 

According to Spot On Chain, Wynn currently holds 1,687.33 BTC in a long position, valued at roughly $178 million. The position risks liquidation at $104,610 if Bitcoin continues to decline.

Market data from CoinCodex shows Bitcoin now trades at $105,286 following a 2.9% drop. The total crypto market cap stands at $3.34 trillion, with Bitcoin dominating 62.75% of the space.

Trader 0x2258 Profits by Countering Wynn’s Moves

As Wynn’s losses mounted, another trader, using the address 0x2258, reportedly gained by betting against his trades. 

According to Lookonchain, this address made $17 million by going long when Wynn shorted and shorting when Wynn went long. The strategy proved effective as the market moved in the opposite direction of Wynn’s positions.

This approach highlights how certain traders capitalize on patterns and sentiment shifts, especially during periods of high volatility. With Wynn’s trades becoming public, they provided signals others could act on.

Bitcoin’s price volatility remains intense, with over $402 billion traded across crypto markets in the past 24 hours. 

Although the Crypto Fear & Greed Index indicates a greed level of 60, 89% of assets have lost value. Wynn’s decline underscores the risks of over-leveraging in the crypto market.

Meanwhile, traders like 0x2258 demonstrate that strategic positioning and timing remain key to navigating crypto price swings. As sentiment fluctuates, traders continue adjusting their positions with caution.