Legendary Trader James Wynn: From PEPE Millionaire to Bitcoin Billionaire Player

The cryptocurrency market was rocked last week as Bitcoin surged to a record high of $112,000, with prominent trader James Wynn, a self-proclaimed “high-risk leverage enthusiast,” at the center of the storm. Wynn’s dramatic shift from a $12 billion Bitcoin long to a $10 billion short position has sent shockwaves through the market. Today, Wynn posted a cryptic message claiming to “leave the casino” with $25 million in profits, sparking debates about whether he truly intends to exit trading.

The PEPE Success That Made Him a Legend

James Wynn’s crypto journey began with a meteoric rise through the memecoin PEPE. In April 2023, Wynn invested just $7,600 in PEPE when its market cap was a modest $4.2 million. He boldly predicted a rise to $4.2 billion, rallying community support via social media.

He also used multiple wallets to invest in other memecoins such as ELON and promoted tokens like BIAO, ANDY, and WOLF, earning profits from these ventures. The PEPE trades, along with his activities in other memecoins, established Wynn as a notable “memecoin hunter” and provided the capital and visibility that later supported his billion-dollar trades.

A Week of High-Stakes Maneuvers

On May 19, as Bitcoin neared $105,000, Wynn showcased a $5.7 billion long position with 40x leverage (5,520 BTC) on X, with an entry price of $103,302 and a liquidation price of $98,294. He predicted a rise to $118,000, citing a bullish weekly MACD and $100,000 as key support.

On May 20, Wynn trimmed $1.6 billion from his position, locking in profits while holding $3.72 billion in longs and a 10x-leveraged PEPE position (floating profit of $10.88 million).

As Bitcoin hit $112,000 on May 21-22, Wynn scaled his long to $12.5 billion (11,588 BTC), strategically reducing positions to secure over $40 million in combined profits.

On May 24, fears over U.S. President Trump’s tariff proposals triggered a 4% Bitcoin drop below $107,000. Wynn’s position faced a $29 million floating loss, but he closed PEPE ($25.2 million profit), ETH, and SUI ($5.3 million loss) positions, redirecting funds to Bitcoin, pushing his long to $11.9 billion.

By May 25, his 22x-leveraged position held a $20 million floating loss, with a liquidation price of $104,820.

On May 26, Wynn stunned the market by closing his $12 billion long and opening a $10 billion short (9,402 BTC), with a liquidation price of $110,450. Citing low trading volume, an oversold 4-hour chart, and macroeconomic concerns, he signaled a bearish short-term outlook on X, sparking theories of a “shakeout” to re-enter at lower prices.

Retirement Claim or Market Mind Game?

On May 26, Wynn posted a bombshell on X, declaring he’s “decided to leave the casino” with $25 million in profits, stating, “It’s time for me to walk away a wynner.” The accompanying screenshot showed a total equity of $33.88 million, with $25.06 million in profits, though a staggering 84.34% max drawdown highlighted his risky approach.

Yet, just 7 hours later, Wynn shared another post, stating, “It’s time to go all in again,” accompanied by a screenshot of a new $5 million long position on Bitcoin at 40x leverage, with an entry price of $108,800 and a liquidation price of $103,800.

This rapid change in stance—shifting from an apparent exit to diving back into high-stakes trading—makes it difficult for his fans and followers to discern his true intentions, likely leading them to approach his statements with greater caution. This unpredictability may be a hallmark of a “memecoin hunter” like Wynn, known for dramatic market moves, but it could also undermine the effectiveness of his recent calls, such as his promotion of the new memecoin MOONPIG, as trust in his consistency wanes.

A High-Stakes Journey from the Trenches

James Wynn’s journey from PEPE riches to billion-dollar Bitcoin bets showcases his high-risk appetite, with high-leverage trades often skating near liquidation, reflecting a “dance on the knife’s edge” mentality. This approach has made him a polarizing figure in the crypto space, captivating audiences with his bold moves and dramatic public statements.

Reflecting on his origins, Wynn shared a glimpse of his past on May 22, 2025, via X, recounting how he grew up in a “small shitty town in England that nobody gets out of,” surrounded by “knife crime, drugs, alcohol, [and] poverty.” He described scraping by week to week for small gains until he discovered PEPE on iToken, a micro-cap memecoin that he believed in deeply. Investing heavily and rallying a passionate community, Wynn turned his dream into reality, making over eight figures.

His story—from the trenches to the top—underscores the transformative potential of crypto, they are all legends.