10 WWE Legends Who Should Have Won The Royal Rumble But Never Did

4. Mr. Kennedy

Ken Kennedy is one of the biggest 'what ifs' of the last twenty years in WWE. He seemed to have everything going for him when he debuted in 2005: good look, decent in the ring and, most important, bucket loads of charisma. Yes, Kennedy had 'it'. He was going to be a star and WWE helped him as much as they could, putting him in the ring with top stars like Batista and The Undertaker and giving him his own personalised entrance. People were so high on Kennedy's potential that it wasn't long before comparisons to The Rock and Steve Austin were being thrown around although they, in hindsight, seem a tad ridiculous now. WWE could and maybe would have had Kennedy win the Rumble if he didn't get injured so much and at unfortunate times. He missed the 2006 Rumble due to a serious injury. 2006 would have been a good time for Kennedy to win it, since WWE seemed intent on pushing him to the top early. A Rumble victory would have quickly cemented Kennedy as a star in the eyes of the fans but, sadly, it was not to be. Kennedy did win the Money In The Bank ladder match at WrestleMania 23 but had to vacate the briefcase because of, you guessed it, another injury.