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Mickey Drexler’s Redemption

With the Gap, Mickey Drexler changed the way the world dressed. Then he was abruptly fired, and hired by J.Crew. Can the “merchant prince” make the cash registers ring again?


(Photo credit: Phillip Toledano)

The end was abrupt. As chief executive officer and the driving creative force behind the Gap, Mickey Drexler had built the humble discount-jeans emporium with the groovy seventies vibe and goofy jingle into an international arbiter of style and a global megabrand. He had tossed out the Gap’s product line and reinvented it from scratch, redesigned the company’s stores from floor to ceiling, and ushered in breakthrough ad campaigns, from “Individuals of Style” (Whoopi Goldberg, Spike Lee, Lorraine Bracco) to “Who Wore Khakis?” (Andy Warhol, Marilyn Monroe, Picasso). By introducing consumers to stylish-but-affordable basics—khakis, pocket tees, prewashed jeans—Drexler exploded the myth that good taste has to be expensive. He allowed the masses to look good without going broke, and in the process, he not only changed the way the world dressed and built the Gap into a $14.5 billion behemoth. It could be argued that he invented casual chic.

In May 2002, however, Drexler found himself in trouble. The veteran retailer had many skills, foremost among them a seemingly magical ability to divine what clothing styles would separate consumers from their money. But recently, Drexler had made a series of bad calls. Faced with increasing competition from a pack of imitators—everyone from Abercrombie & Fitch to Wal-Mart—he decided to steer the Gap away from its signature basics look to a trendy, Britney-esque aesthetic: cropped T-shirts, low-rider pants, brighter colors. The result was a 29-month slump. Drexler had lived through ups and downs before, but nothing like this. “I was damned nervous,” he says. “I kept thinking, We’ve got to fix it. The press and the stock market were killing us.”

Even as Drexler mounted a massive turnaround effort—firing staff, transferring executives, commissioning new merchandise—tensions that had long simmered between him and the Gap’s board began to boil. Having come of age in the sixties, Drexler was a retailing maverick. When choosing product, he made decisions with his gut, not market research and spreadsheets. As a manager, he let it all hang out, doing a victory dance when he was pleased, yelling when frustrated, leaving endless “What if . . . ” “Why not . . . ” voice mails. There was a time when that kind of freewheeling spirit suited the Gap; you could argue that it was vital to the company’s success. But the Gap was a Fortune 500 megalith now—more grown-up, more corporate—and there were rumblings on the board that Drexler was no longer the right man to lead the company. “Mickey wasn’t so passionate about compensation committees and budgets and strategic plans,” says a former board member. “We knew the company couldn’t continue to operate with a master merchant driving the brand. My own view was that there should be a transition to a more management-oriented CEO.”

It didn’t help that friction was growing between Drexler and Gap founder Donald Fisher, whose family owned one third of the company’s stock. “Mickey was given 99 percent of the credit, but Don had started the company, and maybe he felt he deserved more credit than he was getting,” says John Bowes, a philanthropist and high-school classmate of Fisher’s, who invested in the launch of the Gap and was on the board for 21 years before retiring in 1997. Two of Fisher’s sons had worked at the Gap during Drexler’s tenure. “It puts extra strain on the relationship,” says Bowes, “when the founder’s kids come in and start running a division.”

When Drexler was fired from the Gap, he insisted on addressing the board. His remarks were mostly a howl of rage. “Where is your decency, your integrity?” he asked.

On the evening of May 21, Drexler met with the Gap board at the company’s San Francisco headquarters to show off the latest merchandise, insisting that he’d “fixed” the clothing. Drexler and the board had a friendly dinner afterward. At home that night, Drexler got a call from his friend and Gap board member Steve Jobs, the Apple CEO. Jobs had not attended the board dinner, but was calling to alert Drexler that an unspecified change was in the works. Drexler won’t talk about the events of that week, but according to several people who spoke with him at the time, he had no hint until that night of what was to come.

The next morning, Fisher called Drexler in and fired him. Drexler insisted on addressing the board immediately. His remarks were mostly a howl of rage. “Where is your decency, your integrity?” he asked. “It was a very emotional scene,” says a board member. Later that day, Drexler negotiated an agreement to stay on until the company found a successor, and that afternoon, the Gap announced Drexler’s upcoming “retirement.” The next day, the company’s stock fell 15 percent by the closing bell.

On September 26, 2002, the Gap named Disney theme-park executive Paul Pressler its new CEO; the day before, Drexler had been given 24 hours notice to clean out his office. (Don Fisher declined to be interviewed, but through a spokesman sent an e-mail saying of Drexler, “He was a great partner. In 2002, the size and scope of our company required different leadership skills to move forward, and it was time for another change.”) A month after Drexler’s ouster, Gap’s sales rebounded strongly, thanks largely to the new merchandise Drexler had ordered. One board member called to congratulate Drexler and thank him; Fisher later sent him a case of wine. The gestures were of no comfort. Nineteen years, billions of dollars in sales, and one fashion revolution after he joined the Gap, Mickey Drexler had been shown the door.

It’s early September in Manhattan, and at Bryant Park, workmen are putting the final touches on the tents constructed for Fashion Week. Mickey Drexler, meanwhile, is taking in a different fashion show. Inside J.Crew’s headquarters at Broadway and 9th Street, the company’s two top designers are unveiling J.Crew’s 2005 summer line. Drexler strides the cramped hallways, and a conga line of 50 staffers tails him. Dressed in his standard uniform—J.Crew unstructured blazer, white Helmut Lang button-down over a gray J.Crew T-shirt, Diesel jeans, argyle socks, suede Tod’s—Drexler launches into a pure stream-of-consciousness riff of love-hate reactions. “Ooh,” he gasps at the sight of a women’s beige fitted jacket on a mannequin. “I love it, it’s so beautiful.” When womenswear designer Jenna Lyons raises a cost concern—“We wash it and you lose a lot of leather, so it’ll be expensive”—Drexler brushes aside the comment. He’s got a feeling about it. He’s certain it will sell. Entering a room where men’s and women’s T-shirts and blouses and shorts are in various shades of olive and purple, Drexler says, “I don’t get the colors here.” He asks menswear designer Todd Snyder to get rid of the matching stripe on the pocket of a man’s T-shirt that also has a green stripe on the collar. “It’s too much. This is a reason not to buy it—an ‘I love it but . . . ’ ” Scanning other merchandise, Drexler points out more details that seem wrong to him: the shiny grommets on a weathered overnight bag, the too-large pocket on a men’s jacket, the madras pants with shrill colors—“Am I the only one who hates this?” Then a pair of men’s seersucker shorts catches his attention. The fabric has been washed and faded and rumpled so the shorts look like every guy’s old, can’t-give-’em-up favorite. It’s as if the shorts speak to Drexler viscerally. “This is a monster!” he roars. “No one’s doing these. This makes everything else seem old—this is why I love this business!”

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