2017

Who won: Randy Orton
Who should have won: Bray Wyatt
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A year later, it seems so weird to say that Bray Wyatt was on the up and up as 2017 began, but he was. His latter-half 2016 story with Randy Orton had fans genuinely intrigued and he was beginning to rebuild the credibility he'd lost in years past. A Royal Rumble win and a victory over John Cena at WrestleMania to avenge his 2014 loss would have elevated him tremendously.
Instead, Randy Orton won in a move that felt very random while Bray Wyatt won in an equally random-feeling Elimination Chamber. His sole purpose as champion was to job to Randy Orton at WrestleMania, who in turn was purposed with jobbing to Jinder Mahal. The feud along the way was one of 2017's worst.
Another lost opportunity.