9. Grant Hill
Brand move: Fila to adidas to Nike
A couple years after jumping into the NBA with Jamal Mashburn, Fila signed Grant Hill to an $80 million deal in 1997 (only $10 mil less than Bron-Bron's Nike deal six years later.) During his time with Fila, Hill only played 249 games in nine seasons due to injuries—that's 27 games a season. Hill averaged more games at Duke. Hill spent a few years in Orlando with adidas dealing with more injury issues before landing in Phoenix and signing with Nike and playing a major role for the team in his late 30s—but 30 is the new 20, right Jay? Hill's foot and ankle issues, while not necessarily related, unfortunately brought Fila as much bad PR as their initially signing him brought good.