I think there's almost two different things to think about here and we're kind of ignoring one of them. The one we're talking about is cup vs. shield, but the other way to look at this is cup with almost all the teams in it vs cup with just the top two or four teams. I think that's why the shield matters to a lot of people, because entry into the cup tournament is almost too easy (or another way to look at it is you have to really suck to not make it in). It's like the hockey playoffs; almost everyone gets in so why even bother playing the season? Baseball's the same way now with the three wildcard teams in each league.
So perhaps the shield people (me included) feel that the shield is a "true" measure of who's good and who isn't, where the current cup is slightly devalued because almost everyone gets in.
So perhaps the shield people (me included) feel that the shield is a "true" measure of who's good and who isn't, where the current cup is slightly devalued because almost everyone gets in.