Pete Rose
It’s a shame that Rose’s legacy is beyond repair but he may enjoy having a chip on his shoulder. Cooperstown will never induct the Reds icon because of his gambling scandal. It doesn’t matter that he had a phenomenal playing career and was blossoming as a pro baseball manager.

Rose admitted that he had a gambling problem and even bet on Cincinnati’s games. In the end, MLB hit him with a lifetime ban from the sport and also destroyed his Hall of Fame dream. Some people think that he did enough as a player to earn a sport but others believe that his case is beyond reprieve (via History).