Bitcoin’s recent rebound caught many traders by surprise, including high-leverage speculator James Wynn, who has taken an aggressive stance betting on a market decline.

Despite the optimism surrounding the potential end of the 40-day U.S. government shutdown, Wynn went “all-in” on short positions, risking substantial losses in pursuit of profit.

Liquidation sprees test Wynn’s resolve

The unexpected market recovery inflicted heavy losses on Wynn’s main Hyperliquid account. Over the past 24 hours, his account underwent 12 liquidations, dropping the wallet’s value to just $5,422, according to Hyperdash data.

However the past two months were no different, Wynn has faced a total of 45 liquidations:

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Data from blockchain analytics platform Lookonchain shows.

Before the recovery, Wynn had multiple Bitcoin short positions, essentially wagers on a decline in Bitcoin’s price. These positions, often leveraged, amplify both gains and losses, making the strategy highly risky in volatile market conditions.

Wynn goes all-in

Undeterred by the repeated liquidations, Wynn transferred nearly all his stablecoin holdings into his short positions, expecting Bitcoin to drop below $92,000.

Wynn wrote on his X:

“In the past few hours, I have deployed all stables (30%) and thrown it all on top of my short positions. No joke. As all-in as I can get,”

Adding:

“I’m either going to make hundreds of millions from my leverage short positions or I will go bust.”

At the time of reporting, Wynn’s main account held a 40x leveraged short position worth $275,000 in Bitcoin. The position faces liquidation if Bitcoin’s price rises above $106,856. Wynn initially opened the trade when Bitcoin was below $101,800 and had an unrealized loss of $11,147 as of Monday morning UTC.

Smart money also positions for downside

Wynn’s approach reflects a broader trend among high-leverage traders. Analytics from Nansen indicate that many of the industry’s most successful traders, categorized as “smart money,” are also positioning for further downside. The net perpetual short position on Hyperliquid reached $223 million on Monday, with $5.2 million in new shorts opened within 24 hours.

The episode underscores the volatility and risk inherent in high-leverage trading, particularly during periods of macroeconomic uncertainty. While the potential resolution of the U.S. government shutdown has lifted broader market sentiment, traders like Wynn remain firmly on the defensive, betting on a Bitcoin pullback in an unpredictable environment.

A familiar risk appetite returns

Wynn’s conviction hasn’t wavered despite the heavy liquidations. In a surprising turn, the trader recently returned with two new high-stakes bets, a $19.5 million long position on Bitcoin and a $100,000 long on the meme token Pepe, both placed with heavy leverage.

According to blockchain tracker Hypurrscan, Wynn’s Bitcoin position carries a 40x leverage and was entered around $67,000, with a liquidation level near $65,750. His Pepe position, valued at over $102,000, carries a 10x leverage, though its liquidation price remains unclear.

Wynn has previously accused market makers of targeting his positions, claiming they intentionally drove Bitcoin’s price below his liquidation thresholds.

After losing a $100 million leveraged trade in late May and another $25 million shortly after, Wynn’s return underscores both his resilience and his appetite for risk.

Another well-known trader, Qwatio, has also joined the fray, opening a 40x short worth $2.3 million after being liquidated eight times in a single week.

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