#3 Shane Douglas
While he may not have been hugely popular with a younger audience, Douglas was a wrestling star during the early ’90s. He began his storied career in the WWF, before eventually jumping ship to the ECW just three years later.
Douglas was an instrumental figure in the development of the ECW and was a driving force behind the name change to Extreme Championship Wrestling in 1994. Given this success, he was re-signed by WWF in 1995, a decision I’m sure all relevant parties regret even today.
A large reason for his failure upon his return was a relatively poor gimmick, a school teacher with a chalkboard. The gimmick lasted for just 3 months before Douglas came out and verbally attacked McMahon in the press, which he continues to do to this day.
As a guy who prefers to conduct his dealings behind closed doors, McMahon is never happy about these types of public comments. Negotiations to bring Douglas back to the WWF in 1999 failed and I doubt the two are on speaking terms now.