James Wynn Opens $1B Bitcoin Short, Saylor Hints At Another Buy

A crypto trader on the platform Hyperliquid named James Wynn has opened a nearly $1 billion short bet against Bitcoin with 40x leverage, while Michael Saylor hints at another Strategy BTC buy.

According to a May 25 X post by on-chain analytics platform Lookonchain, Wynn “opened a $BTC short position of 1,038.7 $BTC($111.8M) at $107,711.1 an hour ago, with a liquidation price of $149,100.”

With this recent trade, Wynn has put almost his entire wallet, which holds nearly $50 million, on the line.

Wynn Closes His Massive Bitcoin Long Position At A Loss 

The move by Wynn comes just hours after the trader closed a massive long bet.  

With that long bet, Wynn opened a $1.25 billion position with 40x leverage as well. He even predicted that Bitcoin would soar to $110K on May 24 Saturday.

I think $BTC shoots to $110k today

— James Wynn 🐳 (@JamesWynnReal) May 24, 2025

However, Bitcoin’s price only rose from around $107,300 to about $108,000 on Saturday. This prompted Wynn to cut his losses on the position, which, according to Lookonchain, stood at approximately $13.4 million.

Saylor Teases Another Strategy Bitcoin Buy

While Wynn bets against Bitcoin, Strategy co-founder Saylor has teased yet another Bitcoin purchase by his firm even after the leading crypto pulled back from the all-time high (ATH) of $111,907.17 it set on May 22. 

I only buy bitcoin with money I can’t afford to lose. pic.twitter.com/h7pnFB8yvU

— Michael Saylor (@saylor) May 25, 2025

“I only buy Bitcoin with money I can’t afford to lose,” Saylor wrote to his 4.3 million X followers in a May 25 post. He also included a snapshot of the SaylorTracker chart in the post. 

Over the past few weeks, Saylor’s posts that included the SaylorTracker chart have been followed by an announcement of a new Strategy Bitcoin purchase. If the firm does announce another buy today, it won’t only boost its current holdings of 576,230 BTC, it will also mark the company’s seventh consecutive week of Bitcoin purchases. 

Related Articles:

Best Wallet – Diversify Your Crypto Portfolio

• Easy to Use, Feature-Driven Crypto Wallet
• Get Early Access to Upcoming Token ICOs
• Multi-Chain, Multi-Wallet, Non-Custodial
• Now On App Store, Google Play
• Stake To Earn Native Token $BEST
• 250,000+ Monthly Active Users