TLDR
- James Wynn shifted his focus to PEPE after losing $27.9 million on two major Bitcoin positions.
- On May 26, he opened a $1 million long position on PEPE with 10x leverage through the Hyperliquid platform.
- Wynn’s PEPE position has already gained over $434,000 in unrealised profit as the token rallies.
- The memecoin surged 90% in May and showed strong technical signals, with bullish support from moving averages.
- Analysts expect PEPE to reach $0.000021 if it breaks the key resistance level of $0.000017.
Renowned crypto trader James Wynn has turned his focus to PEPE after closing two prominent Bitcoin positions at a combined $27.9 million loss. Known for bold, leveraged trades, Wynn opened a 10x long position on PEPE through the Hyperliquid platform on May 26. The move comes amid renewed momentum in the memecoin market and improving sentiment across the broader crypto space.
Wynn’s Bitcoin Bets Result in $27.9M Loss
James Wynn opened a $1.26 billion long position on Bitcoin using Hyperliquid’s high-leverage options. Bitcoin dropped from $108,921 to $107,746, forcing Wynn to close at a $13.4 million loss. He narrowly avoided liquidation, which would have triggered at $105,179.
James Wynn just opened a $75 million Bitcoin long.
Does he know something we don't? pic.twitter.com/tpJxFsdUnZ
— Lark Davis (@TheCryptoLark) May 26, 2025
Within hours, Wynn switched to a bearish stance and opened a $1 billion short on 9,402 BTC with 40x leverage. This position also failed as Bitcoin held steady around $107,000, leading to another $15 million loss. Both trades left Wynn with a $27,908,962.20 deficit in just 21 hours.
He cited weak volume and macroeconomic tensions, including a new 50% tariff proposal, as reasons for his Bitcoin outlook. However, Bitcoin’s resilience countered his expectations, leading to back-to-back exits. Despite this, Wynn resumed trading with a fresh $75 million long at 40x leverage, which remains active.
Wynn Opens 10x Long on PEPE Amid Recovery Signs
Shifting strategy, Wynn entered PEPE with a $1 million long position on May 26 at $0.014086 per token. The position totals 1,388,696,014 KPEPE and is up $434,867.01 in unrealised profit. Earlier in the day, Lookonchain reported that the position was only $130,000 in profit.
I feel safe in $pepe 🐸 💚
nfa. dyor. pic.twitter.com/d7p3lAV6Zx
— James Wynn 🐳 (@JamesWynnReal) May 26, 2025
PEPE is now trading at $0.014404, targeting a key resistance of $0.000017. If it breaks through, analysts project upside toward $0.000021. This level reflects a 40% potential increase from the current price.
The memecoin has gained 90% in May after breaking its consolidation on May 8. It remains above both the 20 EMA and 50 SMA, which signal continued bullish momentum. These indicators provide strong technical support that may help sustain upward price movement.
PEPE Aligns With Wynn’s Memecoin Strategy
Wynn’s history with memecoins includes major wins on PEPE, Fartcoin, and Trump tokens. His 2023 PEPE trade turned $7,000 into $25 million, establishing his reputation as a high-stakes memecoin trader. He is also backing his own token, Moonpig, which has surged 3000% in three weeks.
His current PEPE trade marks another calculated entry into a surging asset with rising interest. Technical signals and volume activity support the bullish case, consistent with his past trading behavior. As PEPE trends higher, Wynn appears to be positioning for another potential breakout.
