Air Jordan IX

Who: Anfernee "Penny" Hardaway
Original Release Year: 1993 
Complex Says: After His Airness took early retirement, the league and Nike scrambled to find a heir to the throne. With a few strong candidates from the previous draft class Penny Hardaway stood out due to his freak size for a one man and his marketability. Nike hooked the kid up with an Orlando colorway version of the IXs that Mike himself never laced up in as a Bull and a few years later MJ returned the favor rocking Penny's Air Flight Ones in a game against the Magic.