In the rich history of WWE, there have been a lot of great moments that will be remembered for making the fans happy or celebrating a major accomplishment. But even a company like WWE has its fair share of bad days, with some of them being so bad that Vince McMahon will never forget them for as long as he lives. From unexpected fan reactions, to Superstars making questionable decisions outside of WWE, to his own personal and business decisions, Vince has had to do damage control over the course of his entire tenure as Chairman. No matter how much Vince tries to bury things in the past, pretending that they never happened, deep down Vince must certainly be haunted by the events that happened in the past. This list will showcase the fifteen most significant days that will haunt Vince McMahon forever. These are days on which terrible things happened for Vince, whether from a personal or business perspective. These were days on which Vince lost some or all control over the actions that happened vis-à-vis WWE and he had to do whatever he could to fix these problems. Sometimes he succeeded, while during others he failed. In any case, here are 15 days from the last twenty years or so, including 5 from 2014 alone