From Billion-Dollar Bitcoin Bets to Pepe Pumps: James Wynn's Crypto Gamble

The trader known as 'moonpig' flips from record BTC positions to high-leverage memecoin plays, sparking debate about risk and reward in the crypto space.

Author
Branden Chen
Senior Crypto AnalystMay 26, 2025
Bitcoin trading chart with upward trend

From Whale to Memelord: James Wynn's Pepe Pivot

James Wynn, a pseudonymous trader known as 'moonpig' on Hyperliquid, has once again captured the crypto world's attention. Just days after orchestrating a record-breaking $1 billion notional position on Bitcoin, Wynn has turned his sights – and a portion of his profits – to the memecoin PEPE.

From Bitcoin Titan to Frog Flipper

Wynn's recent trading activity has been nothing short of dramatic. After closing a $1.2 billion BTC long position at a $17.5 million loss, he doubled down with a $1 billion short, leveraging his entire $50 million wallet. He then famously closed that short position booking profits of $25 million.

In a stunning shift, Wynn is now long on PEPE, leveraging $1 million at 10x. That's quite the change in strategy. His rationale isn't clear but the position is already showing a $500,000 profit.

Key Takeaways

  • High-Risk, High-Reward: Wynn's journey underscores the volatile nature of crypto trading, where massive gains and losses can occur rapidly.
  • Memecoin Mania: The move into PEPE highlights the continued allure of memecoins, even for seasoned traders.
  • Market Sentiment: Wynn's actions are closely watched, and his shift into PEPE could signal a broader trend or influence market sentiment.

Is this a calculated risk or a high-stakes gamble? Only time will tell if Wynn's frog-themed foray will prove as profitable as his Bitcoin bets.

Final thoughts

His tweet really says it all - "Now decided to leave the casino with my $25,000,000 profit”. Was this just a gamble? Can this approach be repeated by other traders?

Investment Considerations

As always, investors should consider their risk tolerance and investment timeline before making allocation decisions. Bitcoin remains a volatile asset despite increasing institutional adoption.

This article is for informational purposes only and should not be considered investment advice. Always consult with a qualified financial advisor.

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