4. Shaquille O'Neal 

Brand move: Reebok to Dunkman 

Let's be honest, no sneakerhead really cared about Dunkman, but the fact is that at the time Shaq left Reebok he had pop culture status like Michael Jordan and Michael Jackson. He was winning games, shattering backboards, drinking Pepsi during Super Bowl commercials, starring in films, and even spittin' 40 bars. No player has quite had the same Hollywood appeal as Shaq. O'Neal's line with Reebok was on point, some underrated kicks and even a classic with the Shaqnosis. The fact that this man walked into a Nike meeting his rookie year draped in Reebok should have been enough for the brand to do whatever was necessary to keep The Big Diesel laced in Reebok for life—they did it for A.I. Instead, he went the Payless route, and—say what you will—gave a lot of kids a chance to wear the same shoe as their hero.