Mr Kennedy is one of the few WWE Superstars who were unfortunate enough to win the Money In The Bank Briefcase but not win the World Title because he lost the contract to Edge.
During his recent appearance on Wrestling Inc Podcast, Kennedy revealed that the original plans were for him to cash in the contract on The Undertaker at WrestleMania 24, but they were changed after Taker suffered an injury and he was told that he would cash in the contract earlier than originally planned:
“Taker got injured and he had the world title at the time. They were trying to figure out a way to get it off him, You know, they called me in the office and said, ‘Hey I know we were going to have you cash it in at WrestleMania next year but we need to get the title off of Taker so we’re going to have you come out next week at SmackDown and you’re going challenge him after he has the cage match with Mark Henry and blah, blah, blah, you’re going to win the title.'”
Tough things obviously didn’t turn out this way either and it was Edge who later cashed in the contract on Taker. According to the star now known as Mr Anderson, it happened because he himself suffered an injury just a few days later in a match with Batista:
“I ended up going to see a doctor, take an MRI in Erie, Pennsylvania, the next day Stephanie called me and said, ‘Ken you tore your triceps off the bone, you’re going to have to have surgery and you’re going to be out for seven to eight months. But unfortunately we still have to get that title off of Taker so we’re going to fly to Penn State, Edge is going to challenge you for the briefcase and he’s going to go on to do what you were going to do.'”
It’s worth noting here that Mr Kennedy won the Money In The Bank contract at WrestleMania 23 and lost it to Edge in a match during the May 7, 2007, episode of Raw.
After this incident, Kennedy never came this close to becoming a World Champion in the company again and he was later released from WWE in 2009.
One can only imagine how things would have turned out if the former US Champion would have cashed in his contract on The Undertaker and became the World Champion.