An overall interesting post. I've always thought Yankee fans ridiculously bitter viewing every season they don't win it all as a total failure, as if anything else that happens -- first place, postseason series wins, MVPs, Cy Youngs, All-Stars etc. -- is meaningless.
Those feats have meaning to a lot of fans, and can be fun times for those rooting for their favorites.
I only quoted your line about Fred because I look at it as the opposite -- if by O you mean Optimistic -- because those who are always Pessimistic can't really be disappointed if they're wrong, because that would mean good things actually happened.
Pessimists like to set low expectations because then they can possibly be pleasantly surprised.
Then again, we could probably do an all-day thread trying to define the difference between those who are pessimistic and we Realists...