Year: 2010
Problem: Dov Charney was making too much money with the American Apparel ads/branding, so Gap's team thought it might be fun to pull some 48 Laws of Power trickery and attack AA on its own turf. Gap's logo team blew everyone's bonuses on a Helvetica package, and the rest of the story is last week's history.
Complex says: Rebranding is tough, and as a rule, the public despises change. If you're going to do it, though, stick to your guns. Otherwise a bunch of design bloggers are going to get medieval on you out of their mom's basements.