A high-stakes wager has landed a crypto trader in the headlines. He’s known online as James Wynn, and he’s placed almost $1 billion on Bitcoin rising further. He started piling into a bullish position last week and hasn’t said when he plans to exit.
Bitcoin Bets Hit Billion Dollar Mark
According to Wynn’s posts on X, his position reached about $1 billion on May 21. He’s using $20 million of his own funds and borrowed to make the trade roughly 40 times bigger than his stake. The bet sits on Hyperliquid, a decentralized exchange where traders can open perpetual futures positions. Wynn has already closed part of it, trimming the size to just over $800 million as Bitcoin climbed.
Lookonchain data shows he jumped in around a BTC price of $108,084 and set his “kill switch” just below $103,640—so if Bitcoin dips that far, the whole trade goes bye-bye. As of early Thursday, that bet was sitting on a cool $40 million in unrealized gains.
Source: HyperDash
Trader’s Past Success With Memecoin
Wynn didn’t emerge from nowhere. In 2023, he predicted the Pepe memecoin would hit a $4.2 billion market value. That bet paid off in a big way when Pepe peaked at more than $11 billion in December 2024. A wallet tied to “jwynn.eth” even sent $7 million of Pepe tokens to Binance in May 2024. Based on reports, that move helped him pull in eight-figure gains.
Bitcoin just broke through $111,900!
Top trader @JamesWynnReal‘s 40x leveraged long position of 10,200 $BTC($1.14B) is now sitting on an unrealized profit of over $39M!https://t.co/Xy0EC0h5Cw pic.twitter.com/5UlbeiA984
— Lookonchain (@lookonchain) May 22, 2025
Huge Risk Tied To Price Drop
His trade isn’t without danger. If Bitcoin falls below $100,850, the position could be wiped out. Wynn has said he’d add more money rather than face liquidation. In turbulent markets, minor declines can be the trigger for cascade-like forced liquidations. Any substantial amount of money put into the market begs the question: If prices were to shift just a few percent in either direction, would serious losses be incurred?
Market Logic Favors This Move
Reportedly, the May chances of Bitcoin hitting $115,000 are pegged at 64% or thereabouts, as per Polymarket. Standard Chartered’s Geoff Kendrick also has a bullish view. He predicts Bitcoin could top $120,000 before the end of July. Those forecasts line up with Wynn’s own target of $115,000–$118,000 by the end of next week, and even $118,000–$122,000 shortly after.
Update on my little $BTC long position.
Reduced position size today, took some profits around $110k -$111k.
Seemed like a nice spot to TP, and seems others are doing the same right now.
In my opinion bitcoin is dying to breakout higher. My target remains the same of… pic.twitter.com/BUfWTuqpoU
— James Wynn 🐳 (@JamesWynnReal) May 22, 2025
Positioning In A Shaky Market
Bitcoin had reached about $111,800 on May 22, 2025, before the slight pullback. Traders pointing at rapid gains also warn of quick drops. On decentralized exchanges, the funding-rate costs might add up. Large orders on Hyperliquid might face slippage, which would move the market against Wynn should he try to unwind too quickly.
People see the trades and think its some high level stupid gambling kinda shit, and yes it is. But it is backed by my own thesis. Which in turn, is a calculated risk.
Since local bottom of 74k bitcoin has remained in this channel. Touching the bottom acting as support just two… pic.twitter.com/wenpkcWKrG
— James Wynn 🐳 (@JamesWynnReal) May 20, 2025
Calm Words From A Risk-Taker
“People see this as high-level gambling, and yes it is,” Wynn said. He added that his bets rest on what he calls a solid thesis. Whether he’s right or wrong remains to be seen. For now, his willingness to risk large sums has drawn both admiration and caution from onlookers.
Featured image from Unsplash, chart from TradingView
