High Stakes bets landed crypto traders in headlines. He is known online as James Wynn and has nearly $1 billion on Bitcoin’s rise. He began to pile up in a bullish position last week and didn’t say he was planning on leaving.
Bitcoin bets reached the billion dollar mark
According to a Wynn post on X, his position reached around $1 billion on May 21st. He has used $20 million of his funds and borrowed it to make it roughly 40 times larger than his stock. The bets lie in high liquid, a decentralized exchange that allows traders to open permanent futures positions. Winn has already closed some of it, trimming its size to just $800 million when Bitcoin climbs.
LookOnChain data shows he jumped into the $108,084 BTC price and set the “kill switch” below $103,640. So if Bitcoin soaks it far away, the whole transaction will be goodbye. As of early Thursday, the bet was sitting on a cool $40 million with unrealized profits.
Source: HyperDash
Past successes for traders at Memecoin
Winn did not appear out of nowhere. In 2023, he predicted that Pepe Memecoin would reach a market value of $4.2 billion. The bet paid off in December 2024 when Pepe peaked at over $11 billion. The wallet, tied to “jwynn.eth,” sent a $7 million Pepe token to binance in May 2024. Based on the report, the move helped him take on the eight-course win.
Bitcoin just beat $111,900!
Top Traders @jameswynnrealLeveraged long position of 40 times more than 10,200 $ BTC($11.4 billion) is currently sitting in unrealized profits of over $39 million! https://t.co/xy0ec0h5cw pic.twitter.com/5ulbeia984
– lookonchain (@lookonchain) May 22, 2025
Major risks related to price drops
His trade is not without risk. If Bitcoin falls below $100,850, you can clear your position. Wynn says he’ll add more money rather than face liquidation. In turbulent markets, it could trigger forced liquidation like cascades. The market is costly to a fair amount of money, which raises doubts: if prices change by only a few percent in either direction, will there be serious losses?
Market logic supports this move
The chance that Bitcoin will hit $115,000 is reportedly locked at 64% or that era, according to Polymet. There is also a bullish view of Geoff Kendrick from Standard Chartered. He predicts that Bitcoin could exceed $120,000 by the end of July. These forecasts will line up with Wynn’s own targets of $115,000-$118,000, and even $118,000 to $122,000 by the end of next week.
My small update $ BTC Long position.
Today’s position size reduction took some profits from around $110,000 to 111k.
It seemed like a good place for TP, but others still seem to be doing the same thing.
In my opinion, Bitcoin wants to break out higher. My target remains the same… pic.twitter.com/bufwtuqpou
– James Wynnreal (@jameswynnreal) May 22, 2025
Positioning in unstable markets
Bitcoin had reached around $111,800 on May 22, 2025, before a small pullback. Traders pointing to rapid profits are also warning of quick drops. Decentralized exchanges may add up the funding costs. Large orders for high lipids may have slipped.
People are looking at the deal and thinking about that high level of stupid gambling shit. that’s right. But that is supported by my own paper. This is a calculated risk.
Because the 74k local bottom remains in this channel. When you touch the bottom, there are only two support… pic.twitter.com/wenpkcwkrg
– James Wynnreal (@jameswynnreal) May 20, 2025
A calming word from a risk taker
“People see this as a high-level gambling. Yes,” Wynn said. He added that his bets depend on what he calls a solid paper. I can’t see if he’s right or wrong yet. For now, his willingness to take a large amount of risk has drawn both praise and attention from the onlookers.
Unsplash featured images, TradingView charts
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