James Wynn jumps back into Hyperliquid with mammoth bet after losing $100m on Bitcoin moves

First, James Wynn lost a Bitcoin bet worth $100 million.

Now he’s back betting on leveraged long positions on Bitcoin worth $20 million.

“I’m coming back for it all,” said Wynn on X.

Wynn’s bet comes just as Bitcoin’s price has hit an all time high. It has since dipped, and Wynn says this is “beautiful timing” to go long.

He’s not alone. Investors have poured about $1.7 billion into leveraged positions on Hyperliquid this week, according to DefiLlama.

Hyperliquid is a decentralised exchange that allows traders to use leverage with size comparable to centralised exchanges like Coinbase or Kraken.

Leverage trading, a strategy Wynn employs, has become increasingly widespread onchain. It gives bettors leverage up to 100-times that of the investment — typically unavailable to retail in traditional finance.

Wynn’s trade history

Wynn initially gained a following on X with his memecoin trades. In 2023, he predicted that the market value of Pepe would reach $4.2 billion. At the time, the market value was only $4.2 million, and Pepe reached a peak of $11 billion in 2024.

He claimed to have made eight figures from his Pepe trade alone, though DL News could not independently verify the boast.

With his profits from memecoins, Wynn tried his hand at leverage trading. He began to trade on Hyperliquid in March. He placed large trades on Bitcoin, Pepe, and Official Trump.

In May, Wynn added $20 million in a leveraged trade on Hyperliquid 40 times larger than the amount he put in.

The position was worth over $1 billion at its peak. His unrealised profits reached over $100 million, but as the price of Bitcoin slid shortly after, he lost almost everything in that wallet.

At the start of May, Wynn launched his own memecoin, Moonpig.

As he gained popularity as one of the most profitable Hyperliquid traders, the token rose to a market value of over $120 million. Once Wynn lost the $100 million bet, the token dropped 98%.

But, all of these losses did not deter him from continuing to place highly leveraged bets.

“I’m back in the casino,” said Wynn on June 10.

According to lookonchain, a wallet analyser, Wynn opened a new account and deposited over $2 million. He immediately opened leveraged long positions on Bitcoin and Pepe, which were liquidated within days. He closed the account by withdrawing $137,000 USDC.

Throughout June and July, Wynn continued to place losing trades. He deposited about $27,000 twice and collected referral rewards to continue trading, losing it all in the process.

On July 15, Wynn deposited $466,000 from Binance into Hyperliquid, immediately placing $20 million worth of leveraged long positions on Bitcoin.

Within hours, he lost $46,000 as his long was partially liquidated, bringing his Bitcoin position down to $16 million.

Wynn’s losses for this trade have exceeded $200,000, but he is yet to close his position manually.

“For me, it’s all or nothing,” said Wynn on X.

Zachary Rampone is a DeFi correspondent at DL News. Have a tip? Contact him at zrampone@dlnews.com.