#1 Mr Perfect
The man who most deserved a Rumble victory was Curt Hennig. The second generation star is widely considered the most underrated competitor in both WWE and WCW history and never really got a deserving push to the main event stage, despite having some of the most iconic matches of that era.
Allowing Perfect to win the Rumble at any stage between 1990-1996 would have catapulted him into the main event stage, and was there anyone more deserving of such a push during that period?
Is this man the funniest man in wrestling?
When various stars such as Sgt. Slaughter, The Ultimate Warrior and British Bulldog ( who was deserving, but not as much as Hennig) were pushed during this period, undoubtedly some genius inside WWE HQ could have allowed him his moment with the likelihood of failure remaining slim.