Having finished up KHR’s Varia arc, it’s time to take my first go at parsing out my favorite character. Incidentally, there will be spoilers up to there, in here.
I think a major key to Hibari’s character really is his guardianship: the cloud that can never be bound. For someone like that to be a Guardian, I think he would have to be loyal, not to a person, but to the abstract ideal of the family. Hibari’s attitude toward the school speaks of something similar, to me; he loves the school while seeming to hold every human in it in contempt. This says to me that what he loves and defends is the ideal; defending the actual is kind of incidental.
I think this dovetails with another part of his character. He likes to fight. He likes to win. He likes things to go the way he wants them to go. His ideal gives rise to a vision (an order, as he puts it), and he fights to enforce that vision.
In his own way, I think he’s a complete romantic. It’s just all abstract and he doesn’t actually like the messy humans cluttering things up, however much they’re required. He may feel they don’t understand the ideal well enough.
The things he respects are another clue. He seems to respect both passion and control. Consider that Yamamoto seems to be the only one who can talk him around without getting ‘bitten’. Usually. Similarly, consider Hibari’s reaction during the ring battles, when he says that he’s all for anything that will bring out Tsuna’s true strength. Tsuna is the pure-hearted one, recall, the one who fights for ideals of his own. Hibari seems to respect that, which suggests he understands that.
So I think what we have here is one variation on the Black Knight. Hibari seeks strength/victory/control in order to defend (and enforce) his shining ideal, be it the school or the family.