James Wynn, the high-stakes crypto trader known for outsized, high-leverage calls, is back in profit on his latest bearish wager.
Trading records on derivatives venue Hyperliquid show Wynn's BTC/USD Coin short is up roughly $50,000.
Wynn's short aligns with a market in retreat
Bitcoin has slipped below $104,000, down nearly 2% in the past 24 hours as the broader market saw over $800 million in liquidations, mostly from overleveraged longs, according to data from CoinGlass .
Open interest across exchanges has dropped about 3%, suggesting traders are de-risking after weeks of aggressive bullish positioning. That backdrop may finally be breaking in Wynn's favor.
His $687,000 short from roughly $116,000 BTC is now showing a $50,000 floating profit, with liquidation set at $111,350 - just above current resistance levels on most exchanges.
With longs still being flushed and funding rates turning neutral, Wynn's contrarian stance could prove timely if downside momentum persists. If Bitcoin continues to slide toward $100,000, Wynn's position could compound sharply.
Public portfolio trackers indicate Wynn reactivated accounts and moved new stablecoin capital onchain in October , resuming large, leveraged bets after months of quiet.
Related: What is Bitcoin mining? Explained
A comeback framed by past blowups
Wynn's legend was forged and tarnished in rapid cycles.
Earlier this year he said he was stepping away from perpetuals after flipping several million dollars into far more at the top, then giving it back and accumulating heavy debts. He punctuated that retreat by changing his social bio to a single word: "broke."
Now, with funding near flat and Bitcoin sliding from recent local highs, Wynn's contrarian short has finally tipped green. Whether he can keep it that way depends on the next $5,000 of BTC volatility.
A swift squeeze toward his $111,350 liquidation would erase gains as quickly as they arrived. For now, the scoreboard is simple: short from $116K, up $50K.
At the time of writing, Bitcoin (BTC) was trading at $103,268, down 2.3% in the past 24 hours with a market cap of $2.06 trillion, according to CoinMarketCap .
Source: CMC
This story was originally reported by TheStreet on Nov 4, 2025, where it first appeared in the Trading News & Analysis section. Add TheStreet as a Preferred Source by clicking here.
