The truth about trading with leverage
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Who is James Wynn? Before his headline-making trades, James Wynn was already experimenting with high-leverage strategies on memecoins, an approach that later pushed him into the spotlight. James Wynn is a pseudonymous crypto trader who came to prominence in 2022-2023 via memecoins. One of his earliest public breakout moves was turning a modest investment into a multimillion-dollar return via Pepe (PEPE) when its market capitalization was tiny. That PEPE trade established several hallmarks of his style: high leverage, aggressive risk-taking and a strong “narrative” component with calls on social media and predictions. In early 2025, Wynn moved heavily into perpetual futures on decentralized derivatives platforms, most notably Hyperliquid. These are instruments that allow a trader to open a position with borrowed capital, magnify gains (and losses) and hold indefinitely, subject to funding rates, without expiration. Wynn began running positions with leverage of up to 40x on billion-dollar notional sizes. This transition made him a so-called “main character” in crypto-trading lore: His positions were large, transparent and risky. He became a symbol of what was possible when combining capital, leverage, social visibility and conviction — but also of what could go very wrong. James Wynn’s early PEPE trade and initial profits By early 2025, Wynn was already gaining attention in trading circles after he turned bold bets on Hyperliquid into positions showing tens of millions in unrealized profit. Wynn had significant successes before his more dramatic losses. Inspired by the well-known internet meme, he invested around $7,000 in the PEPE memecoin in 2023, when its market valuation was reportedly under $600,000. The token went viral, helped in part by Wynn’s early entry and promotion through various channels. By mid-2025, PEPE’s market capitalization had climbed to around $10 billion. This matched Wynn’s early forecast of a $4.2 billion market cap, made when…
