#11 Randy Orton (2013)

Now this is where the line between awful winners and satisfying winners starts to blur. Just like John Cena, Randy Orton was a multiple time World Champion when he won the Money in the Bank. However, unlike Cena, Orton was struggling in the mid-card under that bland babyface and needed a change of character. This is exactly what Money in the Bank win gave to The Viper.
Not only did Orton successfully cash in the contract, he did that on the biggest babyface in the company in Daniel Bryan. Even though his program with Bryan generated underwhelming results, it finally gave Orton his first lengthy title reign since 2008 and his second ever 'Mania main event match. The only thing that prevents this from being higher on this list is the fact that Orton was portrayed as a paper champion in this period.
#10 Dolph Ziggler (2012)

Dolph Ziggler has probably seen more crests and troughs in the history of the promotion than any other superstars. He has been defeated by lower mid-card talents and has defeated megastars like John Cena at different times of his career. Ziggler's Money in the Bank win, however, can be termed as the day that started his golden period as evident from the pop that his contract win and subsequent title win generated.
The period between Ziggler's win and cash in was just pure gold, with Ziggler earning vital wins against veterans Chris Jericho, Randy Orton, John Cena, and let's not talk about the moment he won the title from Del Rio. It is undoubtedly one of the best moments in WWE history. Its aftermath - Ziggler suffered a concussion, lost the title to Del Rio two months later, turned face and moved back to the mid-card after Summerslam 2013.