Re: "Should Have" game
Sting should have beat Hogan clean at Starcade 1997. Having that cluster fuck ending after over a year of buildup was a joke.
Bret Hart's debut in WCW should have been delayed until they had an interesting angle for him. He got brought in during the whole Sting/Hogan feud and there wasn't much there for him to do initially. He should have been Hogan's next rival after Hogan was done with the Sting feud.
Nash should not have been the guy to end Goldberg's streak and the finger poke of doom or whatever should have never happened. Having your only semi-young main eventer drop the title to a 40 year old and then having that 40 year old get poked in the chest and drop the title a week or so later to a 46 year old is a good example of why WCW no longer exist.
WWE should have never went with HBK as Bret Hart's survivor series 1997 opponent. Bret didn't want to drop the belt that night anyway but he was never going to agree to drop it to HBK and they should have been smart enough to see that coming. Maybe if the opponent were someone Bret respected more at that time he might have dropped the title.
Kane should have had longer than a one day title run in 1998. All that jobbing to Taker and the one day title run killed a bit of his momentum at the time and a Kane/Austin rematch at Fully Loaded with Austin winning the title would have been a bigger deal than the tag match main event that they did.
Triple H should have won the WWF title at SummerSlam 1999. Really was stupid to have Mick win the SS match clean as a whistle and drop the title the next night on Raw.
Rock vs. Triple H should have been the Wrestlemania 2000 main event. Mick Foley should have won the fatal 4 way if they were that stuck on having the 4 way watch. Mick winning the belt would have at least created a cool Wrestlemania moment. The match is very forgettable in hindsight because it wasn't that good and it had no Wrestlemania moment. The title should have then been vacated with Mick retiring and a tournament should have happened ending with Rock still beating Triple H at Backlash 2000.
Triple H vs. Austin should have been the WM 18 main event. Jericho just wasn't the right guy to put Triple H over and the Stephanie/Jericho tandem just wasn't that good. Triple H beating Austin in that spot would have been a much bigger deal even if he didn't win clean.
Austin should have only stayed heel until the invasion.
WWE should have paid Goldberg a king's ransom to come in during the invasion angle. He could have been a great monster heel and rival for Austin, Rock, Taker etc.
WWE also should have made Booker T. out to be a bigger deal and more serious during the invasion angle. I felt like they made a joke out of the guy.
When the WWE debuted the World Heavyweight Title they should have had a tournament with RVD winning and Triple H then beating him a few months later setting up a good Triple H/RVD feud.