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Originally Posted by Sworn to Believe
Pain created the Akatsuki, you mean? Or Tobi? Not sure what you're trying to say there...
Tobi's plans...God knows what they are. I think there's a lot more to them than either what meets the eye or he tells people they are. Obviously he wants Naruto...and the Kyuubi. Maybe the reason he's trying to gather the tailed beasts is to re-create the Jyuubi (another potential connection to Rikudou Sennin/Sage of Six Paths)?
As for not expecting Naruto to win over Nagato, Tobi doesn't know everything. Perhaps he didn't know the full extent of what Naruto was capable of (not just jutsu/power-wise), and he probably didn't expect the Katsuyu thing and didn't expect Naruto to know enough/figure out enough to survive the destruction of Konoha. And probably expected Naruto to try to defeat Pein/Nagato, not make peace with him and remind him of Jiraiya's (and Nagato's original) ideals. Plus Tobi didn't know that Naruto knew of Nagato's past and all that stuff.
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Well my biggest question is: Who created Akatsuki and for what purpose? Maybe the answer will be revealed to us at the end of the manga, or perhaps I am overlooked some important info.
Edit: Another very important question is, what was the role of pain in akatsuki? (or maybe he is still alive somehow?)