Last year, Gap and Kanye West signed a ten-year deal.

News of the deal sent Gap's stock fling, and their first collaboration -- a jacket -- was a huge success.

Yet, former Gap CEO Mickey Drexler thinks the deal will be a bad one for both parties.

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“I probably shouldn’t say this but I told him he shouldn’t do the deal because it doesn’t make any sense in my opinion,” he told Yahoo Finance. “I have a lot of friends at Gap still, but it doesn’t work for someone like Kanye. He is not a corporate person and Gap is a big corporation.

So, I know the jacket sold out. They did $7 million on the jacket overnight. [Kanye] is a smart guy but he shouldn’t have done it. And I don’t think they should have done it, either.”

Dexler and Kanye are known to be friends, so he might know what he is talking about.