#5 Damien Sandow
Damien Sandow will always be remembered very fondly by WWE fans. He had all the tools in his arsenal to become a massive success in the WWE. He had great mic skills, was polished in the ring and could draw in audiences and get an impassioned response out of them. Whether he was the ‘Intellectual Saviour of the Masses’ or The Miz’s stunt double, he thrived in every role he was put into.
Regardless of all his positive traits, the history books will remember Sandow as the man to unsuccessfully cash-in his Money in the Bank briefcase. It can be said that his win in the ladder match and subsequent cash-in both came too early, but his career never truly recovered after his loss to then WWE Champion John Cena in 2013.
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The WWE completely dropped the ball with him on multiple occasions, most notably how they caused considerable damage to his character in an uninspired feud over the MITB briefcase against Cody Rhodes.
The odds of Sandow returning to the WWE and fulfilling his potential are extremely slim as he is considering acting as his next career path. Hopefully, he will attain more success there than he did in the WWE.