25 biggest pro wrestling ‘what ifs’ of the past 25 years

A look at 25 “what if” scenarios of the past 25 years that could have changed professional wrestling.

Where do we start when we discuss some of the biggest “what ifs” in pro wrestling over a certain time period? We talked about the last 20 years but then figured that we’d miss out on too much of the Monday Night War between WWE and WCW. We then talked about possibly hitting the last 30 years, which would have opened up a world of possibilities that would have been very difficult to contain. So we went ahead and made the decision to go in between and hit up 25 of the biggest “what if” scenarios of the last 25 years.

At that point in time in professional wrestling, The Golden Era of WWE was coming to a close. While other superstars had their moments in the sun, Hulk Hogan had been the dominant force in WWE for nearly a decade while Ric Flair had been the driving force behind the NWA and WCW. Flair had come to WWE near the end of 1991 and in a huge “what if” scenario should have played out at that time with Hogan taking on Flair at WrestleMania VIII. However, that moment never came to be and we didn’t see that match until a few years later. That particular WrestleMania wasn’t the greatest and the following year’s edition is still considered by many to be the worst WrestleMania in history. Flair went back to WCW and Hogan would retire in 1993 as WWE, and wrestling as a whole, was about to enter an entirely new era.

For the last 25 years, we’ve seen so many different eras and moments and superstars come and go and it’s crazy to think that everything could have been so much different if just a few things had gone another way. So what we’ll do today is take a look at a few of these events and speculate (because we’re wrestling fans and that’s what we do) on what could have happened if this or that happened and see what that alternate universe might look like.

I expect nothing less than some of you to disagree with some things that I say here so please jump in the conversation once you’re done reading and tell me what you think I missed and create some of your own in the comments section. I’ll start with a few recent things and work my way backwards with a few wild cards thrown in there to shake things up a bit. Without further ado, here are 25 of the biggest “what if” professional wrestling scenarios of the last 25 years.