Did He Learn Nothing? Trader Who Lost $100M Returns With High-Leverage Bets On Bitcoin

James Wynn, the pseudonymous crypto trader known for his aggressive leveraged bets, has resumed high-risk trading just weeks after self-reporting losses in the hundreds of millions.

Known for his audacious trading style on the Hyperliquid HYPE/USD platform, Wynn's journey from meteoric gains to catastrophic losses, followed by a dramatic exit from social media and a bold return, offers a human lens into the allure and peril of crypto trading.

Wynn first burst onto the scene in March 2025, when he turned a $3 million position into $100 million through a series of high-leverage trades, primarily on the meme coin Pepe PEPE/USD.

His most notable feat was transforming a $7,000 investment in PEPE into over $25 million, earning him a cult following among crypto enthusiasts.

"I started trading perps in March, had never traded perps before, in fact, never really traded properly before," Wynn shared on X, admitting his inexperience but reveling in his early success.

His transparency and bold moves drew thousands of followers, who watched his every trade with a mix of awe and apprehension.

However, Wynn's fortunes took a sharp turn in May 2025. ‘

He placed a $1.25 billion long position on Bitcoin BTC/USD with 40x leverage, betting on a price surge above $108,243.

When Bitcoin briefly dipped below $105,000, his position was liquidated, wiping out 949 BTC, equivalent to nearly $100 million.

Just days later, on June 3, Wynn doubled down with another $100 million Bitcoin bet, only to lose $25 million when it was liquidated on June 5.

"With all this new attention, the trading spiraled out of control. I was basically gambling," Wynn confessed on X, reflecting on how the pressure of his growing audience warped his judgment.

The losses didn't stop there.

On July 11, 2025, Wynn's 40x leveraged short position on Bitcoin, worth $1.5 million, was liquidated after Bitcoin rallied past $116,000, contributing to a broader wave of $543 million in short-position liquidations that day.

Also Read: $600M In 1 Day: Why Are Bitcoin, Ethereum ETF Suddenly So Bullish?

Observers on X called his bet a "massive risk," with some suggesting an "Inverse James Wynn" strategy, betting against his moves.

Devastated, Wynn changed his X profile to "bankrupt" and deactivated his account on July 12, leaving behind a void in the crypto community."

He lost $100m gambling on high leverage with bitcoin barely moving," posted Scott Melker on May 30, calling Wynn's story a "cautionary tale."

Wynn's disappearance from X sparked debate about the sustainability of high-leverage trading.

His losses, estimated in the hundreds of millions, underscored the risks of betting big in a volatile market.

"Wynn's dramatic downfall serves as a warning against aggressive speculation," noted a report on ainvest.com, highlighting the need for disciplined risk management.

Yet, behind the numbers was a human story of ambition and overconfidence, as Wynn himself admitted to "not taking the numbers on the screen seriously."

Remarkably, Wynn's story didn't end with his exit.

On July 15, 2025, he resurfaced, reactivating his X account and returning to Hyperliquid with a $468,000 deposit.

He opened a 40x leveraged Bitcoin long position worth $19.5 million at $117,000 and a 10x leveraged PEPE position valued at $102,000.

According to blockchain analytics platform Lookonchain, Wynn funded these trades partly with a $6,792.53 USDC referral bonus.

By July 16, his Bitcoin position had gained $161,200, though it faced a liquidation risk if Bitcoin fell below $115,520.

His PEPE position also showed modest profits of over $6,000.

"Never financial advice of course. But the MM's are out of gun powder," Wynn posted on X, suggesting market makers could no longer manipulate prices against him.

Wynn's return has reignited fascination and skepticism.

While some admire his resilience, others, like trader Qwatio, who opened a $2.3 million short position against Bitcoin, see his moves as reckless. "Don't be a James Wynn," warned Scott Melker, emphasizing the dangers of high-leverage trading.

Yet Wynn's persistence reflects a deeper human drive—a refusal to be defined by failure, even in the face of staggering losses.

As Bitcoin hovers around $117,432 and the crypto market remains a battleground of bulls and bears, Wynn's saga continues to captivate.

His story is not just about numbers but about the emotional toll of chasing wealth in a high-stakes arena.

Whether he's a cautionary tale or a symbol of unrelenting ambition, James Wynn's journey reminds us of the human cost, and allure of playing the crypto game.

Read Next: