10 Wrestlers Who Should Have Won The WWE Royal Rumble
4. Anyone…. (1999)
It’s difficult to pinpoint one person who should have won the 1999 Royal Rumble. Regardless: whoever it was, it shouldn’t have been Mr. McMahon.
In a gimmicky Rumble match, emblematic of the times, McMahon entered at number two and somehow managed to win after a near-57-minute stint that featured, amongst other shenanigans, a spell on commentary and a backstage brawl in which Stone Cold Steve Austin was attacked in a women’s bathroom. Really.
You could make a case for Austin winning, given that he went on to main event WrestleMania anyway, but he’d already won the previous two Rumbles. Triple H or Kane could have been outside bets, although that would have necessitated a change of plan for the ‘Mania XV main event.
Perhaps this was even the stage on which to give Mankind the type of win his popularity deserved. Either way, looking back it’s difficult to believe that a non-wrestling company executive won the Royal Rumble match, especially when you consider how stacked the WWF roster was during the Attitude Era.