#4 Mr. Kennedy (2007)
Some WWE Superstars seem to have the misfortune of pretty awful timing with their injuries. But in this case, along with the timing, the nature of it may have been an even bigger disappointment. That is exactly what happened with Mr. Kennedy, a Superstar earmarked for greatness in the WWE.
After a solid start to his career on SmackDown, Kennedy won the Money in the Bank Ladder Match at WrestleMania 23, and with the Undertaker needing to take some time off to heal a biceps injury, WWE called upon Mr. Money in the Bank to cash in and become the World Heavyweight Champion.
A female WWE star said her life is in danger. Details HERE
The only problem was that Kennedy suffered an injury of his own and was initially thought to be out for 5 to 7 months. WWE booked him to lose the briefcase to Edge, who went on to SmackDown and won the world title. However, Kennedy's injury was not as severe as first thought, and he only missed a few weeks, making the loss of the briefcase unnecessary.
The former Impact World Champion did get another chance at success in WWE, as Vince McMahon's illegitimate son, but he got suspended for 30 days ahead of the big reveal. A world title victory would have been a career-making moment for Mr. Kennedy, and it is a real shame that it was taken away in such cruel fashion.