James Wynn Returns With Millions on the Line in Fresh Leveraged Bets on Bitcoin and Pepe

Despite enduring multiple high-profile liquidations, crypto trader and self-styled market rebel James Wynn is back—and he’s betting big on Bitcoin again.

The pseudonymous multimillionaire, who rose to fame earlier this year after losing tens of millions in leveraged trades, has opened two new positions, suggesting he hasn’t lost faith in Bitcoin’s bullish potential. 

And this time, Wynn is playing with serious fire: a 40x leveraged long position on Bitcoin worth more than $19.5 million, opened at a price of $117,000.

That position has already cost him $1.4 million in funding fees, and it’s teetering on the edge. If Bitcoin drops below $115,750, Wynn risks yet another liquidation. Still, for now, he’s slightly ahead—sitting on $78,000 in unrealized profit, according to blockchain data.

But that’s not all.

Wynn also entered a 10x leveraged long on meme coin darling PEPE, opening a position worth over $102,000 at a price of $0.00001201. While the exact liquidation point is still unclear, the move hints at renewed conviction in the memecoin’s upside—even as PEPE has dipped more than 3% in the past 24 hours.

James Wynn’s positions (Source: Hypurrscan)

A Familiar Comeback

Wynn isn’t exactly new to the spotlight. He made waves in May after a jaw-dropping $100 million Bitcoin long was wiped out in a flash drop below $105,000, triggering one of the biggest individual liquidations the crypto market had seen that month. Undeterred, he tried again in early June—only to be liquidated again, this time losing nearly $25 million.

During that volatile second round, Wynn claimed that his liquidation level was being “deliberately targeted” by major players. “They’re coming for me again,” he warned in a now-infamous X post, adding, “Don’t let these evil bastards liquidate me.”

It’s this underdog narrative—equal parts defiant and delusional—that has earned Wynn a cult following in the crypto community. Many cheer his boldness, while others watch with a mix of morbid curiosity and risk-management horror.

“MMs Are Out of Gun Powder”

In his latest comeback, Wynn sounds more confident than ever. “Beautiful timing for a 40x long,” he posted on X. He even offered a wink to fellow traders, writing, “Never financial advice of course. But the MMs are out of gun powder.”

For Wynn, the implication is clear: the market makers, often blamed for triggering cascading liquidations, might be too exhausted—or out of capital—to push Bitcoin down any further.

Still, the stakes are brutally high. Leveraged trading, especially at 40x, magnifies both wins and losses. Wynn’s own story is a case study in just how dangerous it can be when prices swing even slightly in the wrong direction.

Not Everyone’s Bullish

While Wynn is riding the bull, others are still shorting the market. Notably, trader Qwatio opened a 40x leveraged short on Bitcoin, betting over $2.3 million that BTC will fall. 

Qwatio 40x leveraged Bitcoin short position (Source: Hyperdash)

According to blockchain data shared by EmberCN, Qwatio’s past week hasn’t been pretty—he was liquidated eight times, losing a total of $12.5 million.

As for PEPE, the meme coin remains volatile. After a dip, it’s shown early signs of recovery, but with speculative assets like this, sentiment can turn on a dime.

James Wynn’s Gamble Continues

Whether Wynn’s bold new bets pay off or end in yet another fiery liquidation remains to be seen. One thing’s for sure: he’s brought drama—and attention—back to the high-stakes world of leveraged crypto trading.

For now, all eyes are on Bitcoin’s next move. One slip, and Wynn could lose millions. But if he’s right, he could ride the comeback of the year.