#3 Daniel Bryan
Way back in 2011, it still felt like Daniel Bryan was treading water in WWE. Sure, he'd been able to pick up some momentum courtesy of his in-ring performances, but it felt like he hadn't really locked down what kind of character he was. So then, when he won the Money in the Bank ladder match, you can imagine how many people were taken by surprise.
While he did cash it in and eventually became an incredibly annoying heel, it felt like a waste of a world title run. That role would've been much better suited to someone like Wade Barrett, who was also in the match because he was desperately searching for a way in which to become relevant again.
Fans drowned out a popular wrestler with 'She's a racist' chants recently
The briefcase would've worked well under the ownership of the Englishman, and it could've springboarded his career to the top - much like it did for Edge.