It should be more about emotional investment, I think. Stone Cold Steve Austin started to rise to prominence with his 1996 King of the Ring victory. It was almost two years before he then won the WWE Title, but people followed his journey, and when he did win the belt, there was a reward there.
I don't think a good guy should win "because he's good," or a bad guy "because he's bad," but rather what works for the story. Randy Orton winning the WWE Championship at WrestleMania XXV would have been the best idea, in my opinion, because Orton has been built up to take the title, and as a force that was not going to be stopped. You then build up a force to de-rail him.
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