Interesting! Here are some thoughts.
21. What if Eddie Guerrero hadn’t died?
I think that if Eddie had lived, Benoit wouldn't have done what he did. However, I think both of them were within the next few years of being finished with their in-ring careers. Eddie for sure was getting past his prime. By 2010, one or both of them would be working backstage with Dean.
20. What if Owen Hart had said no to the stunt?
Again, I don't think he really would have had much longer a career. 1999 wasn't like it is now with AJ Styles still in peak condition in his 40s. So I think that by 2003 or 2004, Owen is working backstage. What would change here is that maybe Bret Hart would have feuded with Goldberg in the summer of 99, and wouldn't have taken the long time off that he did, but with the way his WCW time went, his going home after Owen died was probably for the best.
19. What if The Undertaker had lost early in his WrestleMania career?
The Streak wouldn't be a thing, so he may have retired a few years ago. Because if not for him showing up at WrestleMania time, I don't think he would have stuck it out long enough to start getting the Saudi blood money.
18. What if Sting had signed with WWE earlier than he did?
Unfortunately, probably the same thing that did happen.
17. What if Brock Lesnar hadn’t left/never came back to WWE?
If Brock doesn't leave in 2004, Randy Orton doesn't win the World title. Lesnar would still be the youngest champion in the WWE (until Nicholas).
If Brock leaves but then doesn't come back, that would have some minor repercussions, as I don't think Rousey would have come over for the year that she did.
16. What if The Rock doesn’t leave WWE for Hollywood?
He starts getting booed out of the buildings. By 2002, Rock was getting very stale. He would have turned heel at some point, but it wouldn't have been the cool "Hollywood Rock" that everyone fell back in love with.
15. What if The Rock doesn’t join The Nation of Domination?
This one seems interesting, because without that heel turn, he never moves past "Die Rocky Die" chants. Could he have still done a heel turn but not joined the NOD? Probably, but him joining gave him a big boost.
14. What if Triple H had stayed with Chyna?
He still would have gotten the same huge push, but perhaps not as far. He wouldn't be in line to run WWE like he is now, but he still would have had much the same career path.
13. What if The Curtain Call never happened?
Hunter Hearst Helmsley wins the 1996 KotR, meaning "Austin 3:16" doesn't happen. However, Bret Hart would still have chosen Austin in November to feud with, so he likely would have still gotten over as huge as he did.
11. What if Goldberg’s undefeated streak in WCW goes longer?
I think fans would have just gotten bored of it if he was still squashing people on a regular basis. He really did have to lose at some point.
10. What if Sting was the third man in the nWo?
The nWo still would have been big, but not the huge deal that it was. Hulk Hogan being the third man gave it a more mainstream appeal, because everyone knew Hogan. Sting was popular among wrestling fans, but not as much in the major culture. Also, what does Hulk do when he comes back, which inevitably was going to happen? I don't think it would have had as much impact if Hogan ended up being the fourth or fifth man, and the storyline is basically over if Hogan just comes in and superhero triumphs over the group.
However, the nWo still would have been better than the WWF's 1998 "NWA invasion" though.
9. What if Steve Austin stays in WCW?
He gets lost in the midcard, feuding with Brutus Beefcake, Jim Duggan, and Johnny B. Badd until he retires early.
8. What if Stone Cold had to retire after SummerSlam in 1997?
Assuming that Brian Pillman still dies. Without Austin vs. McMahon, the Attitude Era ends up not working out, and we would today be watching the WCW Network.
7. What if Hulk Hogan never signs with WCW?
WCW stays afloat based on loyal fans and Ted Turner, but there's no Nitro, no nWo, and no profit, so the second AOL/Time Warner can, they get closed off, just like in real life.
6. What if Vince Russo never goes to WCW?
I'm not sure how much changes, really. The writing was already getting worse, and while Russo's changes did turn away some fans, the Nitro ratings were still better than current WWE are pulling in. Does this scenario mean Russo stays with the WWF? Because if not, then maybe he would end up finding a way to still get involved with NWA:TNA, but starting it earlier.
5. What if Eric Bischoff had bought WCW?
I don't think NWA:TNA happens if WCW stays around. Also I don't think the WWF ends up doing the brand split, unless they think they have absolutely too many people, but the brand split (from what I've read) was originally meant to be WWF and WCW because of everyone who came in during the invasion. It would have taken some time for WCW to gain more traction after losing in the Monday Night War, but they would have kept a level of fanbase, a lot of the fans who left completely when WCW died.
4. What if The Invasion angle had all the main players involved?
WCW would have had bigger names, but they'd have still had to look like jobbers to the guys like Taker and Austin.
2. What if the Montreal Screwjob never happens?
The "Mr. McMahon" character would have to have started off something else. I don't think Shawn Michaels retires without that though; sure, him messing up his back had nothing to do with that, but I've always speculated that part of why he got out of the spotlight was because otherwise, "You Screwed Bret" would have followed him no matter what he did in the future, a lot like it did Earl Hebner. Bret may have been more motivated in WCW though, and that would have been good, but it wouldn't do much more than just him giving better matches.
1. What if Vince McMahon goes to jail?
This one could go two ways. As Kenny said, Jerry Jarrett was already in line to run the show, and that could have either seen things change so that the WWF becomes a better watch, or it sees more of the same and Nitro overtakes it sooner because Vince isn't there in 1997 to start moving things more toward Attitude.
