Current position: CEO, J. Crew
Signature move: Success is the best revenge
At Gap Inc., Drexler turned a sleepy denim retailer into an arbiter of casual style and forever changed the way Americans dressed. Then, on May 22, 2002, after 19 years with the company, the last seven as CEO, it all came to a screeching halt. Frustrated by a 29-month sales slump, founder Don Fisher fired The Merchant Prince. “I was devastated,” Drexler told The Daily Beast. “I cried.”
Redemption, it turns out, was just across the shopping mall. J. Crew came calling, and Drexler jumped at the chance to give the down-on-its-luck preppy clothier a new sheen. How did he know it was the right move? “My vision of the future was so compatible with what I thought J. Crew could be,” he says. Seven years later, Gap has foundered, while J. Crew has prospered. Drexler has long since moved past the anger he felt on the day he was fired and even made peace with Fisher, who died in September. “People who have bounced back often say it’s better the second time around,” Drexler says. “In my case, that’s true.”