#1 - Kane
Back in 2010, it was announced that the Money in the Bank pay-per-view would become an annual event and that there would be a ladder match for each brand. Kane was the first man to win the Smackdown Money in the Bank ladder match, but his cash in is forgettable because he only held the contract for around an hour.
The Big Red Machine decided to cash in his contract on Rey Mysterio following the main event of the show where he was successful in becoming World Heavyweight Champion. Kane holds the record as the fastest man to cash in the contract, but he's also one of the most forgettable contract holders.
Edited by Nikki La'ulu