James Wynn, a crypto trader who once turned $7,000 into over $25 million, has returned to high-stakes trading just weeks after losing nearly $100 million. Known for his aggressive use of leverage, Wynn's rise and fall has become a symbol of both the thrill and danger of crypto speculation. His initial success in early 2025 turned him into a cult figure, especially after flipping meme coin PEPE trades into eight-figure profits. But by May, it all unraveled. A $1.25 billion leveraged bet on Bitcoin went south, followed by another $100 million position that was also liquidated. He later admitted the attention got to his head and likened his trading to gambling. After being wiped out again in July by a failed short position, Wynn deactivated his X account and labeled himself "bankrupt." Many in the crypto community viewed his story as a cautionary tale of ego and poor risk management. Still, Wynn resurfaced on July 15 with a $468,000 deposit and new high-leverage bets. His latest positions have shown modest gains, but many traders remain skeptical. Whether he’s on a comeback path or headed for another crash, Wynn’s story continues to fascinate—and warn—those in the crypto world.