James Wynn has returned to long bets of $23 million on ETH and PEPE despite losing $100 million in Bitcoin trades earlier this year.
Wynn's risky bet on PEPE is nearing liquidation with high financing costs, yet he continues to double down on extreme leverage.
Stable ETH funding rates show bullish trader sentiment, but Wynn's moves reflect the risks of chasing gains without risk limits.
James Wynn, the controversial cryptocurrency trader known for his high-risk positions, has returned to the spotlight with new multimillion-dollar bets. According to Lookonchain, Wynn recently deposited $536,573 in USDC into Hyperliquid. He then opened new buy positions - 3,269 Ethereum worth $12.12 million and 812.16 million of kPEPE worth $11.28 million. Wynn's trading moves have sparked new interest, especially after he lost a previous position on Bitcoin worth $100 million in May 2025.
Throughout the period from April to July, Ethereum funding rates remained mostly positive, ranging from 0% to 0.015%. These rates reflect the amount traders pay to maintain leveraged positions. Typically, high rates indicate a bullish market.
Source: Coinglass
However, analysts warn that this could also indicate excessive activity. Notably, financing spikes peaked in mid-May and July during sharp price volatility. Ethereum prices ranged between $2,000 and $3,500 during this period. These patterns confirm strong bullish activity with short periods of slowdown.
Wynn doubles down despite previous losses
Despite his previous failures, Wynn continues to make bold trades. He built a concentrated PEPE position, starting with 18,153 tokens, which then surged to over 6 million in 95 minutes. Entry prices ranged between $0.011999 and $0.012015.
Trading values ranged from a few hundred to over $72,000. At one point, his PEPE contract achieved an unrealized profit of $1,708.16. However, his risks remain high. His funding rate is -7.22%, with a liquidation price of $0.00001137.
Furthermore, PEPE was recently trading at $0.00001213, down 3.7% over 24 hours. The day's lows approached Wynn's liquidation threshold at $0.00001175. Thus, his bet is unstable. Wynn's history exacerbates the situation. In May 2025, he lost 949 Bitcoin, which was then valued at $100 million, after a sharp price drop.
Trader or Gambler
Wynn once admitted on X that he was "actually gambling." He denied being a professional and warned others not to imitate him. Days later, he bet $100 million on Bitcoin again.
He even accused market makers of manipulating his positions. As a result, he sought help from the cryptocurrency community. He received funds from at least 24 wallets. He later liquidated 240 Bitcoin worth $25 million to stabilize his deals.
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