#1. Rey Mysterio
Rey Mysterio's World Heavyweight title win at WrestleMania 22 was one of the most feel-good moments at the time. After Eddie Guerrero's tragic death, Mysterio's momentum catapulted and everyone from fans to backstage officials wanted to see Mysterio win.
All but one man wanted it - Vince McMahon. Ex-WWE creative writer Court Bauer described the situation, stating that McMahon was essentially pressured into making Mysterio World Champion even though he didn't believe him to be one, saying "He'll never be my World Champion".
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As a result, McMahon finally relented, but stated the exact date when Mysterio would be dropping the title. To add to his misery, Bauer said that McMahon buried Mysterio every opportunity he got, citing it as a reason why Mysterio wouldn't succeed.
This is the saddest case of McMahon just making someone world champion out of pressure. Mysterio would end up having a short, forgettable reign with the title.