Grant Hill
Before Hill broke his foot, he was one of the best NBA players in the league. Unfortunately, this catastrophic injury changed him forever and was also a severe blow for the Magic. The resulting surgery almost killed him but luckily he survived the nightmare. Hill entered the Hall of Fame because he did enough during his glory years.
However, he never succeeded in winning an NBA ring. The closest he came to this was playing in the Western Conference finals with the Suns. Amazingly, he made his first playoff appearance after 15 years in the league and set a record in the process. They lost the six-game series against the Lakers (via NBA.com).