19. Tracy McGrady
If we’re being honest, Tracy McGrady was one of the most physically gifted players in decades. At 6’8, McGrady was the type of do-it-all wing player that so many NBA teams absolutely salivate over in today’s era of basketball: someone who could legitimately play five positions on the basketball court, and present athletic mismatches at every one of them.
But despite all of his career accomplishments, including seven selections to an All-NBA team (which includes two First-Team selections), some people say McGrady suffered from what some would describe as “good stats on bad teams” syndrome. For his all of his abilities and scoring prowess, he was never considered a “winner.” Who knows how history would have looked back on him if Grant Hill didn’t suffer his career-derailing injuries when he and McGrady signed with the Orlando Magic in the summer of 2000.