Crypto Whale James Wynn's $87M Portfolio Wiped Out in 5 Days: A Detailed Recap

TL;DR

• James Wynn – an industry participant known across the digital asset space for his high-risk leverage trades – became the latest rock star of crypto by making some jaw-dropping trades before the latest Lookonchain update revealed a total wipe-out.
• In a twist, an anonymous trader profited $5.6M in three days by consistently taking the opposite side of his trades.

The Adventures of Wynn

Earlier this month, he entered a long BTC position with roughly $390 million. The bet initially had a liquidation price of $96,600 and a margin of just south of $10 million. In the following days, Wynn increased the position to a whopping $1.25 billion with 40x leverage. 

At one point, the trader was at the crest of the wave, standing at the staggering $87 million in unrealized profit due to BTC’s price rally above $110,000. However, towards the end of last week, the asset’s valuation (and the entire cryptocurrency market) retraced following Donald Trump’s threat to impose tariffs of 50% on the European Union, effective from June 1. 

Logically, the downtrend wiped out a significant chunk of Wynn’s gains. He then flipped bearish on the asset, opening a short position of 1,038 BTC at $107,711 with a liquidation price of $149,100. Eventually, the trader called it quits, closing all contracts with a profit of $25 million.

The whale’s actions were praised by many X users, with some calling him a “legend.” Others, though, have not been so kind, wishing to see him in the red. Wynn prepared a special post for those stating:

For all my haters out there who so very much loved to see my portfolio swing down by $60,000,000.

Just know, now you get to see it swing BACK UP INTO THE HUNDREDS OF MILLIONS.

I repeat HUNDREDS OF MILLIONS.

Money that haters like you can’t even dream of having because… pic.twitter.com/VnFo6i5bhT

— James Wynn (@JamesWynnReal) May 27, 2025

The blockchain analytics platform Lookonchain revealed that just a few hours after announcing the profit, the trader “was back in the casino” and continued to long BTC with 40x leverage. “The portion size reaches 684 BTC ($75.34M), and the liquidation price is $103,120,” the entity stated on May 26. Subsequently, Wynn increased his long position to 5,676 BTC, with a liquidation price of $108,010.

Besides interacting with BTC, Wynn is known as a proponent of PEPE and opened several positions involving the asset. Back in the day, he spent $182,000 to purchase 7.2 trillion tokens. He sold 6.76 trillion PEPE for almost $34 million and left 443.7 billion PEPE (worth over $6 million at current rates). 

Lookonchain revealed that Wynn had been actively trading the meme coin on Hyperquid lately, making four profitable trades that netted $25.4 million. 

The platform later estimated that the whale deposited 240 billion PEPE into Binance, raising the question of whether he was preparing to cash out. Shortly after, the entity disclosed that it seemed like Wynn had sold the stash to fund his long BTC position and informed that he deposited the remainder of his PEPE holdings into the exchange. 

Betting Against Wynn and Big Loss

The whale executed his whopping long and short positions on the decentralized exchange Hyperliquid, and these trades were visible to other market participants. Lookonchain revealed the case of one savvy trader who bet against Wynn’s actions and, in just three days, made $5.6 million. 

Specifically, they shorted BTC every time Wynn went long and vice versa. On May 24, trader 0x2258 opened a short position in BTC and ETH and closed it the following day, realizing a profit of $1.36 million.

Then, Wynn opened a BTC short position, while the other trader went long on BTC and ETH, only to make a profit of $2.54 million on May 26. Finally, the unknown industry participant opened short positions on the two cryptocurrencies, generating a profit of $1.7 million (at least on paper). 

Some speculated that the mysterious trader might be Wynn operating from another account to hedge his bets. However, the whale rejected the rumors, saying:

“Not happy with this post at all. Whoever trader 0x2258 is, it is not me and have no clue who it is. I only trade on one HL account and that’s public. Don’t start spreading fake news with zero proof.”

The most recent Lookonchain update, though, paints a painful picture for the whale. It reads that it took him 70 days to build the aforementioned $87 million portfolio (at its peak) but only five days to lose almost all of it.

James Wynn(@JamesWynnReal) has wiped out almost all his profits on #Hyperliquid.

It took him 70 days to go from 0 to $87M+ in profit, and only 5 days to lose almost all the $87M+ in profit.https://t.co/IUTpCuzoSB pic.twitter.com/n2p3nftZ3G

— Lookonchain (@lookonchain) May 28, 2025