Career years: (1994-2006); (2008)
: Magic, Suns, Knicks, Heat
Career stats: 15.2 ppg, 5 apg, 4.5 rpg, 1.6 spg
Accolades: 4x NBA All-Star (1995-1998), 3x All-NBA (1995-1997), NBA All-Rookie First Team (1994)
Reason for fall-off: Injuries

Penny was on his way to the Hall of Fame. However, Lady Luck had different plans. In 1998, Hardaway injured his left knee and was never the same again. Although he played for 14 years, the real Penny was only here for four seasons. In those first few years, Hardaway put up 19.7 points, 6.7 assists, 4.6 rebounds, and 1.9 steals. He also carried the Magic to a Finals appearance along with Shaquille O'Neal and was a favorite for brands trying to sell us stuff. His legacy remains intact, however, with his signature Nike line still pulling in money.