I think there was one of these in the past but can't find it but feel free to combine with other famous what ifs.
But here is one that was recently debated with a friend.
What if Chavo got the world title push instead of Rey? I mean they already were abusing his name. Why not give it to him? He lacked the mic skills, but could have easily had a mouth piece. He didn't even get a mid card push. Heck, even his caddie got a better push. But how do you think it could have worked?