#2 Chris Jericho (WWE WrestleMania 33)
Chris Jericho has won several world titles in WWE, including the time he defeated The Rock and 'Stone Cold' Steve Austin in one night. But he did not win any during his last seven years with the company. The closest Jericho came was during the early days of the second brand split, on Monday Night RAW.
He formed a partnership with Kevin Owens on RAW, one filled with genius heel tactics, hilarious comic timing, and of course, the 'List of Jericho'. The pair were the most entertaining characters on Monday nights for a long time. It did help that KO was the Universal Champion, while Jericho was getting more and more over with the fans.
WWE had plans to have this partnership explode in the main event of WrestleMania 33, with Jericho defeating Owens to win the Universal Championship. Unfortunately for JeriKO, there was a more attractive proposal for the Universal Title at 'Mania.
Brock Lesnar suggested an extension of his story with Goldberg, which would see him lose at Survivor Series before defeating the WCW legend for the Universal Championship at WrestleMania. Vince McMahon liked the idea and decided to have Jericho and Owens fight for the United States Title instead.
It was a massive disappointment, considering how hot the angle was following the 'Festival of Friendship'. A segment like that deserved to set up the WrestleMania main event, not second on the card. This drop in position may have contributed to Chris Jericho's decision to leave WWE.