Unfortunate Fate of Mr. Kennedy’s Notorious MITB Win

Before the failed cash-ins and stolen briefcases, the Money in the Bank was one of the most prestigious wins in WWE. It wouldn’t just guarantee you a shot at the gold; it could potentially thrust you into stardom! The sky was the limit for Mr. Kennedy after winning the MITB briefcase at WrestleMania 23. But what followed was a rollercoaster of emotions and highs and lows…

Mr. Kennedy after winning the WWE Money in the Bank Ladder Match at WrestleMania 23.
Mr. Kennedy after winning the WWE Money in the Bank Ladder Match at WrestleMania 23.

Mr. Kennedy and the Push That Never Came in WWE

With his memorable entrance and impressive mic skills, “Mr. Kennedy” Ken Anderson quickly made a name for himself after debuting on SmackDown on August 25, 2005.

He would soon emerge as one of the top heels in WWE, feuding with notable names such as Undertaker, Batista, and Eddie Guerrero.

His star was on the rise, and on February 27, 2007, Mr. Kennedy defeated Sabu in an Extreme Rules match to qualify for the Money in the Bank Ladder Match at WrestleMania 23.

Kennedy would ultimately win, allowing him the right to challenge any world champion in WWE at any date up until WrestleMania 24.

Yet, he would never reap the benefits that fellow MITB winners would.

The initial plan for WrestleMania was for Edge to win the Money in the Bank briefcase for a second time. However, plans changed three days before the event, and Mr. Kennedy was now swapped in for the victory.

“They were still talking about Edge winning,” Mr. Kennedy explained on the WINC Podcast back in 2017. “Then, three days out to the pay-per-view, they switched it and went my way.

“I knew it was possible that right before our music hit, they could have said, ‘No, we’re going to go with CM Punk.'”

Fortunately for Kennedy, plans were not changed, so in front of 80,000 fans at Detroit, Michigan’s Ford Field, Mr. Kennedy fended off the likes of CM Punk, Edge, Randy Orton, and The Hardy Boyz to win the Money in the Bank briefcase.

After his big victory, the plan was for Mr. Kennedy to cash in his MITB at the following year’s WrestleMania. He’d soon announce these intentions on April 30, 2007’s episode of Raw.

However, things would change a few days later.

World champion at the time, The Undertaker, got injured, and plans soon began to unravel for Kennedy.

“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.'”

Mr. Kennedy continued, “‘We’re going to have you come out next week at SmackDown, and you’re going to challenge him after he has the cage match with Mark Henry,’ and blah, blah, blah. ‘You’re going to win the title.'”

The date was set. Mr. Kennedy was finally going to become a world champion.

However, his promised championship victory would never come.

Plans Derail at a House Show

At a house show just days after being promised championship gold, Mr. Kennedy took a clothesline from Batista that caused injury to his tricep.

Kennedy talked of his conversation with Stephanie McMahon after his subsequent MRI and doctor’s visit.

“[Stephanie told me], ‘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.'”

Stephanie continued, “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.”

Backstage Perception of Mr. Kennedy

Jim Ross spoke about the backstage perception of Mr. Kennedy at the time on his Grilling JR podcast.

“He was positioned to take the next step. That’s why he won the Money in the Bank ladder match,” JR would say.

“I think [Mr. Kennedy] was the guy. Vince McMahon had great confidence in his potential, and he believed this kid had something. To be the chicken-s*** heel, he’s not going to overpower you with his size; he’s gonna beat you by his cunning skill set, cheating to get an unfair advantage, as Ric Flair did forever.”

WWE Executive and Producer Bruce Prichard also spoke highly of Mr. Kennedy on his podcast Something To Wrestle With Bruce Prichard.

Co-host Conrad Thompson asked Bruce, “For him to win the Money in the Bank, it feels like a strong vote of confidence from the office, does it not?

Bruce replied, “Everyone was behind Kennedy at that point. We were really looking for some big things from him.”

Conrad Thompson would later ask, “If he was so over and the office was behind him, what’s the thinking in taking the briefcase away from him?”

Bruce replied, “He was injured. He couldn’t go, so he was out. We had to move on.”

Mr. Kennedy’s dream of becoming a world champion slipped away.

Regrets for Mr. Kennedy

After his tricep injury, WWE sent Mr. Kennedy to see a surgeon, who informed him that it was just a hematoma. Instead of being out seven to eight months,  he would only be out for around three weeks.

Unfortunately for Kennedy, he had already dropped the MITB briefcase, so there was no way to go back on it.

“Ken [told me that] he regrets that he didn’t say something to Steph,” Conrad Thompson expressed to JR. “He felt like he was essentially giving up an opportunity and not putting up a fight for it. Maybe people got the wrong impression but he was just trying to do as they asked.”

“At the end of the day, you want to do what they ask,” Ross added.

JR would follow up by saying, “Ken should have had a nice, pleasant conversation and pitched his idea. Stephanie would have listened and she would shared the information with her father. If Vince liked it, he may have gone for it.”

Details on His WWE Release

Mr. Kennedy was never back to the same level after returning from injury. While the Rated-R Superstar got the main event push, Kennedy was thrust down to the mid-card after his return. Just two years later, on May 29, 2009, he would be released by WWE.

His firing would happen four days after fellow wrestler Randy Orton complained to WWE management that Kennedy was reckless in the ring, noting a botched backdrop caused Orton to land on his head and neck instead of on his back. Orton disputed that this could have ended his career.

According to Kennedy, Orton also convinced John Cena to complain to Vince McMahon about Kennedy’s in-ring performance, which led to McMahon releasing Kennedy from his contract.

You can learn more about how Randy Orton got Mr. Kennedy fired from WWE here.

A promising run in WWE ultimately cut short.

“Everybody enjoyed working with Kennedy,” Prichard admitted on his show. “Ken was a hell of a talent, a hell of a worker, hell of a talker, and very good in the ring.

“I’ve said it before; I think that Ken, in some ways, was just allergic to success. He just had that mental block when he reached that certain level to go beyond and be the megastar that I truly think he could have been.”

After leaving WWE in 2009, Ken Anderson enjoyed a successful tenure in TNA as Mr. Anderson, eventually becoming a two-time World Heavyweight Champion for their company.

Do you feel Mr. Kennedy deserved a more significant push in WWE? Sound off on our FacebookTwitter, or Instagram accounts to let us know your thoughts!

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Jack Varden is a writer and long-term wrestling fan out of the UK. He can be reached on Twitter @JackVard7.