When: Summer 2003

The closest thing to OJ's murder trial this generation will probably ever see. Kobe's 2003 sexual assault case shocked the world and captivated sports fans and just about everyone else until it was dismissed and charges were dropped in September 2004. Up to that point, Kobe was a clean-cut guy who never got in trouble and used his immense talent and likability to garner tons of endorsements. This case changed the face of his career and persona, he had to work his way back up to his current standing by consistently winning and staying out of the news for anything even remotely related to this. Either way, this is his biggest fail to date because he was either a rapist or at the very least a cheater to the public and had to dish out $4 million on a diamond ring for his wife.