So I've been reading through Naruto again, and Chapters 290 - 300 strike me as very interesting in regards to the recent events concerning Kabuto, and got me thinking about him, and what we know about his character.
He's
an AB Blood Type, and the sole survivor of a massacre, and a medical ninja. Both, the absolute antithesis for anyone who would want to cause a war. He was originally a sleeper agent for Sasori, though while the subject of a brain washing ninjutsu at the time, means that he's essentially the ultimate spy. He went from there to work for Orochimaru, because he liked his way of thinking, and helps to save Orochimaru on multiple occasions.
Both he and Orochimaru are generally anti-Akatsuki: Orochimaru tries to kill Naruto during the Tsunade Arc and mentions Akatsuki/Naruto being problematic in the future, Kabuto seems to abide by assisting the "enemy of his enemy." During Naruto & Neji's match in the Chunin Exams, he heals Hinata, and knocks out Kiba when he seemingly has NO reason to. He mentions when moving to assist Saukra after she's injured by Naruto in his 4-Tails form, that he's intentionally helping them out for the purpose of thinning out Akasuki, because they conflict with his/Orochimaru's motivations.
The only people that I recall Kabuto killing were the ANBU squad guarding Sasuke. That brings up the point that he may or may not have been there to kill Sasuke, and stop Orochimaru, because it's the only time in the series that he's acting without being observed/accompanied by Orochimaru, but he's interrupted by Kakashi so we don't really know what he was thinking.
In addition to that, he keeps leaving breadcrumbs for Konoha to follow what's happening and thereby reduce the overall damage that's done. He's the one who mentions that Hayate's spying on them, which leads to his death, and then a hightened security during the Chunin Exams. He creates a fake dead body of Sai, and leaves stitches oddly so that Yamato can tell that it's a fake. This is similiar to how he leaves the dead ninja that Anko and the ANBU find, and follow to Madara's hideout.
That brings us to the current situation: kidnapping Yamato.
Yamato is one of the few people in the series that is
known to be able to neutralize a Jinchuriki's power. That's
incredibly dangerous in the wrong hands, and could potentially be an immense asset to Madara in stopping the 8 & 9 Tails. On the other hand, I'm wondering if Yamato's abilities might be able to manipulate the cells of the first Hokage, and work against Madara and Zetsu from inside, since he's specifically mentioned to be the only successful of 60 experiments with those cells by Orochimaru.
Overall, I get this feeling that we should be trusting Kabuto, especially since he's expressed interest in Naruto, and it's been stated that Naruto makes friends with everyone he meets. If that's the case, it makes sense that he would be asking about Sasuke, since Sasuke is, in Orochimaru's words, "the bullet that's being used to fuel the war." If he does get Sasuke, he can get him away from Madara's control, because he's one of the few people that really understands how Sasuke's Avenger Complex is making him easy to manipulate, and that the one person's influence that could turn him is Naruto.
All of Naruto & Sasuke's conflicts and intereactions thus far are incredibly brief, so Naruto never really breaks through to him. I get the feeling that Kabuto might be the final piece to get that conflict resolved, but he's also got to deal with the fact that Orochimaru (if he's still alive), will try harder than ever to get Sasuke at that point. On a related note, Orochimaru's body became more awkwardly snake-like in his battle with 4-Tails Naruto, when the host body was starting to fail on him. I think that this may also be happening to Kabuto, which means that this may be happening a lot sooner than anticipated. The only issue here is Madara not wanting to give up Sasuke until
after the war, but Kabuto's as sly as they come...
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