I'm softer on Paul Pressler than most people but this isn't a surprise. But I also don't know that the Gap's problems are as easily laid at his feet as some people want it to be.
Retail clothing is extremely fad driven and cyclical and the heads of these companies seem to flit around on the peaks and troughs that come along. It doesn't matter how cool the Gap remains, in 10-12 years kids don't want to be wearing what the previous mini-generation was wearing.
That said, Pressler was brought in because analysts said that the Gap was having financial problems and needed a financial mind. Then when that didn't actually fix anything for the Gap they've decided that it is because what the company needs is a fashion genius with financial minions.
Pressler came in and pretty much did what he promised and everybody expected. It isn't entirely his fault that this wasn't actually what the company needed (and the people who were certain that the company needed to move in that direction four years ago are now equally certain that it needs to move in a specific new direction).
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