You think 14 year old Obito was more proficient in bijuu control genjutsu than Itachi was?
Actually Yes he is. Obito was more like 15 if he was older than Kakashi by a few months but any ways, Obito was trained by Madara and contains some of Hashirama's cells from his white zetsu parts so all of Obito's powers would be strengthen just like how Orochirama used it to strengthen his edo tensei restraining ability. Also if you go back and reread certain chapters you'll see that Obito controlled Kurama with his basic 3 tomoes Sharingan will Itachi and Sasuke stated they need the MS to do so. Only Madara and Obito were shown to do this feat so I do think Obito genjutsu are more powerful than Itachi's while Itachi use more varieties.
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is where Obito used his 3 tomoes and here is where Itachi and Sasuke statedand agree to needing he MS
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Some people might Say Obito has already awaken his MS years ago so he only needed to awaken his MS to control Kurama even with just 3 tomoes but that would be dumb to say. MS powers up the Sharingan's ability farther than 3 tomoes with their abilities to read movements and such so Madara/Izuna and Obito would had to master he Sharingan to the point of being able to perform a power genjutsu.
In part 1 Itachi went after the Nine Tails, the order most likely came from Pain since Tobi knew the truth about Itachi. Itachi was the only Akatsuki member besides Tobi that was able to capture the 9 tails from naturto.
You do know that Tobi was the one still running Akatsuki from the shadows right? Itachi knew this as well so all orders came from Obito. Also did you forget Itachi's deal with Obito? Not to touch the Village or Sasuke and he'll help him (Obito) kill all Uchiha and join his organization. Uchiha was only assigned the nine tails because Itachi wouldn't let anyone from Akatsuki near Konoha.
