James Wynn Crypto Trader Lost $99M in Bitcoin Bet: Affect Market?

Will James Wynn Crypto Trader’s $99M Bitcoin Loss Affect Market?

James Wynn, a well-known figure from the 2022 bull run, just suffered one of the biggest losses in recent trading history. He lost over $99 million in a single week due to a wrong bet on Bitcoin’s direction. While he went all in using high leverage, another smart trader called “0x2258” made the opposite moves and walked away with a $17 million profit. Lookonchain shared the details over Twitter.

Source: Lookonchain

Back in the 2022 crypto boom, James gained attention for his bold trading style. He even had backing from Alameda Research at one point. But his latest trade turned into a disaster. He was using up to 40x leverage, meaning even a small price drop had massive impact.

Trader 0x2258 Made Millions Doing the Exact Opposite

The key twist? Every time Wynn opened a trade, 0x2258 did the opposite.

• On May 24, Wynn went long on BTC and ETH. At the same time, another trader went short.
  

• On May 25, Wynn closed his long positions, while 0x2258 exited his shorts with a $1.36M profit.
  

• Later that day, Wynn flipped short. Another trader then went long and exited on May 26 with a $2.54M gain.
  

• On May 26 again, Wynn went long—so other one shorted Bitcoin and ETH. That position now has an unrealized profit of $1.7M.

This smart reverse strategy helped 0x2258 earn over $5.6M in 3 days, and $17M in total during the week he was losing big. His major liquidation came when Bitcoin price dropped under $105,000, liquidating 949 BTC, worth $99.3 million.

What Actually Happened: What Does Wynn Think Now?

Bitcoin price had hit an all-time high of $111,970 on May 22, 2025, just around Bitcoin Pizza Day. This sudden rise gave him the confidence to trade big. But BTC soon started falling—dropping nearly 6% this week, and now sits at $105,101.18, down from $107.97K in just 24 hours.

Source: CoinMarketCap

Wynn took to Twitter after his loss, accusing the crypto market of being “corrupt.” He said:

“One thing for sure is that I have exposed just how corrupt these markets are. Guess it’s better to just buy and hold BTC on spot / cold storage it.”

Despite losing millions, he still has mixed views. He warned investors not to expect an altcoin rally unless BTC breaks above its previous highs again.

Source: Twitter

“Most degens are 80% alts. You should be 99% bitcoin and 1% meme because memes outperform everything.”

Will This Loss Shake Investor Confidence?

For many in the market, James's loss is a cautionary tale. It shows how risky leveraged trading can be, even for experienced players. While some may panic, others like 0x2258 prove there’s always another strategy in play. This story may not scare serious investors, but it could push them toward more careful trades and longer-term plans.

In the end, the market keeps moving. Traders win or lose, but smart timing and strong risk control always make the real difference.

Disclaimer: This article is for informational purposes only and not financial advice. Always do your own research before investing in any coin or market strategy.