James Wynn, a prominent figure in the cryptocurrency trading landscape, has once again captured the attention of the market by substantially increasing his long position in Bitcoin. Now holding 7,227 BTC—valued at approximately $790 million—Wynn has set his sights on the ambitious $110,000 price level. This move places his liquidation threshold at a precariously close $107,580, underscoring the high-risk, high-reward nature of his strategy.


A High-Stakes Trading Week


Wynn’s recent trading activity has been marked by both significant gains and notable losses, reflecting his aggressive and fast-paced approach. His latest trading cycle began on May 19, when he opened a 40x leveraged long position on 5,520 BTC at an entry price of $103,302, placing his liquidation level near $98,300—a razor-thin margin given Bitcoin's volatility.


By May 20, Wynn increased his exposure to 7,764 BTC at an adjusted entry of $105,033, shifting the liquidation level up to $100,330. Market volatility tested this position frequently, pushing his margin of safety to the limit.


On May 21, Wynn further increased his holdings to 9,371 BTC, surpassing $1 billion in market value. Unrealized profits peaked at $10.7 million, prompting a partial exit later that day. He sold 2,139 BTC, locking in nearly $12 million in profits and reducing his position to 5,203 BTC, valued at over $550 million.


A Short-Lived Rally and Rapid Reversals


Wynn re-entered the market on May 22 with another significant long position—this time, 10,200 BTC at $108,065. A brief rally to $111,900 pushed his unrealized gains to $39 million, but the surge was abruptly halted. A 4% market correction on May 23, reportedly influenced by geopolitical tensions surrounding former President Trump's EU tariff stance, drove Bitcoin down to $106,700.


Responding to the dip, Wynn expanded his long exposure to 11,588 BTC at an average price of $108,243, moving his liquidation level to $105,180. This aggressive move backfired. He exited on May 25 at $107,746, incurring a $13.39 million loss.


Short Positions and Weekly Drawdown


Attempting to capitalize on the downturn, Wynn reversed his stance by opening a 7,967 BTC short position valued at $856 million. However, the market did not move in his favor. Within 15 hours, by May 26, he closed over $1 billion in short positions, recording a further $15.87 million loss. Losses across Ethereum and other altcoins added to his weekly drawdown, which totaled $60 million.


Despite the setback, Wynn maintained a confident outlook. In a public post on May 26, he acknowledged the week’s losses while highlighting that his account remained $25 million in net profit, up from an initial balance of only $3–4 million. At his peak, Wynn's profits reportedly reached $87 million.


Renewed Momentum: The $110K Bet


Undeterred, Wynn has returned to the market with another bold move: a 7,227 BTC long position at an average entry of $110,084. The position, valued at approximately $790 million, sets his new liquidation level at $107,580—a tight margin that leaves little room for error. If Bitcoin reaches Wynn’s projected $110,000 target, the gains could be substantial. However, the downside risk remains significant should market momentum shift against him.


Market Eyes on Wynn


As the crypto market continues to navigate a complex global macroeconomic backdrop, James Wynn’s high-stakes trading strategy serves as both a spectacle and a case study in risk tolerance and market timing. Whether his current position results in another windfall or a renewed setback, traders and analysts alike remain closely attuned to Wynn’s every move.


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