1989
Winner – Big John Stud
Who should have won – Hulk Hogan
Reason – Ironically this is the only Royal Rumble that Hogan was in that he should have won. Hogan appeared in 4 total, 89,90,91 and 92, and won 2 of those. This however, was the year it would have actually made the most sense for him to win.
This was at the climax point of the Mega Powers team and right before their eventual split. The elimination combination of Hogan eliminating Macho Man Randy Savage and Bad News Brown, should have been the ending sequence and not thrown into the middle of the match. You would have gotten the same payoff, but the show would have ended with Savage and Hogan going nose to nose, to close the night and get everyone talking about, “what happened next”. By having that in the middle of the match, caused it to lose a lot of steam heading into the next Saturday Nights Main Event.
Furthermore, the eventual winner Big John Stud never wrestled again, and went on to do nothing outside of one off appearance at WrestleMania V as a guest referee. This would have put Hogan over and made him the legitimate number one contender heading into WrestleMania V.