Itachi sees what might have been and is left none the better for it.
Heat Visions
"You'll die soon." He says one day, to test the waters. Orochimaru had arrived for their second demon capture, and with him came a boy who looked too ill to be there.
He was Itachi's age, and Leader said conversationally that Itachi should take care of it. This is the second time they've met, after all. And besides, Orochimaru bears watching.
"I think so too. Kabuto-sensei is concerned." Kimimaro tells him. They are wandering up and down the grassy slopes near the Akatsuki hideout, waiting for Itachi's summons and Orochimaru'd dismissal. The earth is sun-splashed and wind-blown, and Kimimaro's hair whips back, revealing a very fragile-looking neck.
"You could probably find a better doctor." Itachi answers. It is not so much that he wants Kimimaro to live, of course. It is that he does not like people who give up too easily. They trouble his precisely ordered world.
"I wouldn't want such a thing. Orochimaru-sama will take care of it as he sees fit."
They're far from the compound now, and Itachi could kill this stupid servant easily, he thinks. Orochimaru would be angry (angrier) with him. Leader would ask, why was it necessary? And Itachi would invent reasons.
Really it is not much better here than it was at home. He is always inventing reasons.
"He doesn't really want you alive, though. He doesn't like sick people." He says instead of acting.
He is thinking, you're not the boy that he really wants, either. But no one needs to hear that. He doesn't like to think of it himself.
There is a silence and for a moment he thinks he's hit on some truth.
"Itachi-san, I don't think you understand whose wishes are paramount here."
Kimimaro smiles, but it is the sick smile of a skull stretching too-thin skin to match. Itachi sees death in him, but it is not the illness (pointed out to him immediately, almost proudly, by Orochimaru himself). There is a fatalism here, or something like it.
He says as much. "I don't understand why you wish to die."
They're silent for a while, staring at the sky. The clouds race by above them and for a moment there are shadows stretching across the long grass.
"It's more that… there are more important things …" Kimimaro finally answers. After a moment's pause, "I think it's something like having a clan, maybe. Something larger than myself."
He smiles again. "Does that make sense?"
It does, and it makes Itachi sick to an almost physical degree to think that such people exist. Kimimaro is not stupid that he can see, not very weak, not a child. He has seen things and done things and destroyed things. There is a moment during which he wants to ask, how can you think so? It's completely irrational.
But that is a redundant question, so he says "No."
"Sorry. I don't really remember my clan very well. It just seemed appropriate."
There is no answer to that, because despite his current position Itachi has been raised to be polite, and pointless cruelty does not come very easily with strangers. Instead he walks Kimimaro back to the compound, so he can sit and regain whatever color the wind has stolen. They talk of other things and Itachi finds that Kimimaro is, after all, capable of smiling in some happy way.
In half an hour Orochimaru returns and comments that they seem to be getting along very well, and perhaps Itachi would like to accompany him back to the Sound for a while?
Itachi knows what's waiting for him there, so he refuses and bids them both goodbye.
He does not see Kimimaro again, and only when news of Orochimaru's death come floating past much later does he realise that Kimimaro died years ago, with no news at all. It suits Itachi that this should be so. Kimimaro with his persistent presence had ruined something of his reasoning pattern.
He still has dreams of it sometimes. Those nights Itachi stays awake and reminds himself that in the game of life he's winning and Kimimaro has long since lost.