Mickey Drexler

Drexler is the clearest example in American retail of a merchant prince: someone who runs a company by touching the product, walking the floor and deciding by feel what a customer will want next season. He grew up in the Bronx, the son of a button-and-fabric buyer, and had rebuilt Ann Taylor when the Fishers hired him in 1983 to run a Gap that had become a jeans discounter. His first act was to throw out every third-party brand and put Gap's name on everything; his second was to make the everything worth buying. Pocket T-shirts in twenty colours, khakis, a denim jacket — basics made to feel like a decision.

Through the 1990s he turned that into a cultural position no clothing brand has held since. GapKids in 1986, Old Navy in 1994, Banana Republic reinvented from a safari catalogue into an urban brand, and the 1998 'Khakis Swing' campaign that made a pair of trousers the most-discussed advertisement of the year. Sharon Stone wore a Gap turtleneck to the Oscars. Revenue went from about $500M when he arrived to $13.7B in FY2000, and he became chief executive of the whole company in 1995. The Old Navy decision is the one I keep coming back to: he launched a brand designed to undercut his own, and it is now the larger business by a wide margin.

The ending is where the record is contested, and Drexler himself has been unusually candid about it. Between 1998 and 2001 Gap roughly doubled its square footage — thousands of new stores, and stores made bigger — on the assumption that demand would follow. It did not. Comparable sales fell for 29 consecutive months, the fashion drifted (Drexler later admitted he 'lost the thread'), and in September 2002 the board fired him. He left with the observation that the company had become too big to be run by taste. He then took J.Crew from a struggling catalogue to a $2B brand, was fired from there too in 2017 after a similar overreach on price and fashion, and has spent his later career as an investor and adviser to smaller brands, including a stint chairing Alex Mill, his son's company. The pattern is consistent: extraordinary at building meaning into basics, and structurally unable to see the point at which growth stops being a merchant's problem and becomes a capital one.