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Also, If Izuna is using Obito's body then how will Kishi explain the masked man who conspired with Itachi during the Uchiha massacre. That masked man was clearly very different to Obito.

Itachi gained his mangekyou by killing Shisu so he probably thought that is the only way to gain the mangekyou. Itachi repeatedly told Sasuke to gain the mangekyou by killing his best friend. Itachi must have known that Naruto was his best freind, so my question is how did Itachi know Sasuke...

Itachi and Tobi both said to Sasuke that they worked together in the Uchiha Massacre. Itachi agreed to help Tobi get his revenge on the clan just as long as Tobi didnt attack Konoha or Sasuke. I know that Itachi put Amaterasu in Sasuke's eye to prevent a meeting between Tobi and Sasuke, but...