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James Wynn’s High-Stakes Crypto Gamble Nears Breaking Point

by Darius Ngetich
May 29, 2025 - 12:00 pm
in Blockchain
James Wynn closely watching Bitcoin price charts as liquidation risk grows

James Wynn’s High-Stakes Crypto Bet Goes Down to the Wire

Crypto trader and market provocateur James Wynn is on the precipice of liquidation after a rollercoaster ride of profits and losses in the crypto markets. With a highly leveraged Bitcoin (BTC) long position hanging in the balance, Wynn’s destiny could be decided with his next trade.

From Meme Coins to Million-Dollar Trades

Wynn is well-known for his bold trading style, frequently placing large bets on meme and relatively lesser-known tokens. According to data from EmberCN, in mid-May he placed a tight trade on Trump (TRUMP) and Fartcoin (FARTCOIN) and gained $11.67 million from May 12–13.

The hot streak didn’t last long, though. On May 23, Wynn’s long ETH and Sui (SUI) positions turned against him and lost him $5.29 million.

Then, an epic comeback. On May 24, Wynn recorded a whopping $42.08 million profit on longs for Bitcoin and PEPE. The profits did not hold, though. Between May 25–27, his BTC short and PEPE long combination failed, burning $16.72 million.

$200M Bitcoin Bet on the Brink

Wynn is now long 1,840 BTC at a notional value of approximately $200.3 million, with 40x leverage. His entry was $109,228, and his liquidation price is $102,257—just 6% below the current BTC price of $108,874.

The trade is already showing an unrealized loss of $718,098. A further drop in BTC would not just wipe out recent profits, but also principal capital Wynn has put into this trade.

Defiant in the Face of Danger

Despite looming losses, Wynn has not lost his swagger. In a biting tweet to naysayers, he tweeted:

“For all my haters out there who so very much enjoyed watching my portfolio swing down by $60,000,000… just know, now you get to watch it swing BACK UP INTO THE HUNDREDS OF MILLIONS…”

Wynn appears unfazed, even energized by the high-risk world he inhabits.

Whale Wallet Suggests Strategic Change

On-chain analytics software The Data Nerd has linked Wynn to a whale wallet which recently moved 44.337 billion PEPE tokens, valued at $6.17 million, to Binance. Acquired at a micro-entry point, the position was reported to have returned 11,117x.

The move may indicate Wynn is preparing to rotate funds or hedge further losses, utilizing the massive profit from his PEPE position.

Will the Gamble Pay Off?

Wynn’s risky approach has earned him wealth as well as derision. With liquidation staring in the face now, the crypto world is watching with bated breath. Whether he manages another unlikely turnaround or faces a catastrophic blowup remains to be witnessed.

Tags: BitcoinRegulation
Darius Ngetich

Darius Ngetich

Darius Ngetich is a blockchain, crypto, and gaming enthusiast. He is also an animator, VFX Artist, and Game Developer, specializing in computers with vast experience in programs like Blender, Unity, and Unreal Engine. My passions are creating games and informing others about the latest developments in crypto, blockchain, and gaming.

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