Following up on my tournament question from a couple of days back: I think one of the biggest (and puzzling) upsets we've ever seen is Greg Valentine sending Ricky Steamboat home in the WrestleMania IV tourney for the world title. We could have seen a rematch from WM III, and even at ten (?) minutes, a Savage/Steamboat rematch would have been a hell of a thing.
It also plays into the narrative of the show: Randy beating all the odds, digging deep, and triumphing over a fresh Million Dollar Man to stand as champion (well, with help from Hulk's chair, of course). Surely having to overcome the man who defeated him one year earlier on his way to facing a rested One Man Gang would have been even better for the story than, “beat Greg Valentine in 5 minutes”.
So what happened? Steamboat still being punished a year after the fact for daring to want a family? Hogan playing his “don't upstage me two years in a row” card? Vince not wanting to give the best match possible to a bunch of Atlantic City douchebags? What gives…?
Steamboat was on his way out and Vince is vindictive are the two most common interpretations of why it was booked that way. Plus doing a face-face match wouldn’t help Savage. Honestly it sucks but it makes sense on a lot of levels.