by 1988 winner Hacksaw Jim Duggan
This is a strange way to begin the legacy of the event by having perennial middle carder Hacksaw Jim Duggan win it. He would go on to WrestleMania IV where he lost to the Million Dollar Man in the opening round of the WWF Championship Tournament in under 5 minutes.
1989 winner Big John Stud
As it turned out, it was his last PPV match with the WWF as an active wrestler. He would make a referee appearance at WrestleMania V and never be heard from again. A giant waste of a winner!
1990 winner Hulk Hogan
The Rumble match itself set up Hogan vs The Ultimate Warrior for WrestleMania VI. To rebook this with 2020 vision, that should been Warrior going over. Hogan would lose against Warrior at WrestleMania VI
1992 winner Ric Flair
A smart move to put Flair over as he also captured the WWF Championship by winning the event. He would lose his belt to Macho Man at WrestleMania VIII
1994 co winner Lex Luger
A result of Vince McMahon never fully being invested in Luger being his guy to replace Hogan. He went with Hart in the long run and it paid off.
Alberto Del Rio
How come The Big Show never went over?
Randy Orton in 09
Batista Bombed!