Crypto Trader James Wynn Loses $99M in Bitcoin Bets, This Counter Trader Wins

Crypto trader James Wynn, who’s been in the news for his high-leverage bets, has lost a staggering $99 million in the past two days with his Bitcoin bets falling flat on his face. With BTC price taking a dip under $105K, Wynn was forced to close all his positions, leading to huge liquidations. On the other hand, a smart crypto trader, betting against Wynn, managed to mint $17 million in the same time.

How Did James Wynn Lose $99 Million in Bitcoin Bets?

Crypto trader Wynn gained popularity in the crypto circle while taking his profits from just $500K capital to a massive $87 million in just two months, through his high-leverage bets on PEPE, TRUMP, and FARTCOIN. However, he continued with the same huge leverage bets on BTC, putting all the profits at stake, and losing a massive $99 million in just a week’s time.

Timeline of Wynn’s Crypto Trades

Wynn stunned the crypto world by turning $500K into $87 million through bold leveraged trading across multiple positions. Below is the timeline of his most successful bets in the period between March 20 to May 23.

• 10x long on $PEPE, amassing $23.8 million in unrealized profit.
• 10x long on $TRUMP, yielding $6.83 million in realized gains.
• 5x long on FARTCOIN, netting $4.48 million in realized profit.

On May 22, Wynn’s high-profile $1.14 billion Bitcoin position was up $39 million, showcasing his extraordinary success.

This is how the crypto trader lost all of his fortune in just a matter of 7 days. 

• May 24: Wynn doubled down on $1.25 billion BTC longs, resulted in a $13.4 million unrealized loss within hours.
• May 25: Switching to $1 billion BTC shorts led to a staggering $15.87 million loss in 15 hours.
• May 30: Wynn faced liquidation of 949 BTC ($99.3 million) as Bitcoin dropped below $105,000.

The volatility in Bitcoin price has revived as US courts go back and forth on Trump tariffs. Coinglass data shows that the 24-hour BTC long liquidations have surged past $200 million.

Crypto Trader Mints $17 Million Betting Against Wynn

Some 17 hours ago from the press time, James Wynn stated that the “comeback will be forcious”. However, it only turns out that the crypto trader was liquidated for 949 BTC. On the other hand, the trader who took BTC bets against Wynn made a multi-million-dollar fortune.

The comeback will be ferocious pic.twitter.com/6954peGIYX

— James Wynn 🐳 (@JamesWynnReal) May 29, 2025

In a surprising twist, a trader with crypto address 0x2258 has found success by consistently counter-trading James Wynn’s positions. By shorting when Wynn goes long and going long when Wynn shorts, 0x2258 has raked in an impressive $17 million in profits, reported LookonChain.