#1 CM Punk (WrestleMania XXIV):
There is a reason that CM Punk's first Money in the Bank victory came out of nowhere.
His win at WrestleMania XXIV would not be the last time the straight-edge Superstar got his hands on the briefcase. He would win the contract the following year as well, but by that time he was an established favourite.
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When the first victory came his way, CM Punk had become a favourite of the ECW fans and was climbing his way up the ladder to an established position on the roster. Despite his apparent rise, WWE did not have any plans which included Punk winning the Money in the Bank briefcase heading into WrestleMania XXIV.
Jeff Hardy had become a main-event player at that point, and WWE had plans for him to win the Money in the Bank briefcase to enable him to win the title at a later date. Unfortunately, a violation of the wellness policy meant Jeff would not be able to implement the well-thought-out plans. The violation saw him suspended, and he had to miss WrestleMania altogether.
Enter CM Punk. Plan B for WWE worked out well for WWE, as he went on to win the match and became the briefcase holder and later the World Heavyweight Champion after cashing in against Edge. As a result, Punk's win was something that no one saw coming, including the company and Punk himself.
You can watch CM Punk leaving the company after winning the Championship against John Cena here:
On a side note, in a cruel irony of fate, Punk's next Money in the Bank briefcase would be used to cash in against Jeff Hardy. Since his first win, the Money in the Bank has become quite the home ground for CM Punk, as he also won the WWE Championship and left the company after one of the best matches of his career against John Cena.
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