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Orochimaru timeline
Let's start with Orochimaru timeline. When did he left Konoha? We know he left because Minato was choosen to be Hokage instead of him. It seems he even stayed for a while while Minato was Hokage:
Presumably he left the village prior to the Kyuubi attack. Given that Minato was not a Hokage during Kakashi Gaiden, Orochimaru left the village 12-13 years before Part I.
And it was stated twice that he left Akatsuki 7 years before Part I, or 10 years before Part II:
So Orochimaru stayed in Akatsuki for 7 years at most.
Itachi's age
Now the problem: Orochimaru left Akatsuki because of Itachi, and he was 17-18 years old in Part I.
So Itachi was a member of Akatsuki at age 11... except that he was not. We have seen Itachi when Orochimaru attacked him:
His stature is close to that of an adult like Orochimaru, which was not the case when he was 13 during the Uchiha clan massacre:
And Itachi did not join Akatsuki prior to the massacre. There are two evidences of that, first that his forehead was not crossed at the time:
And second that he only meet Tobi around the time of the massacre:
Akatsuki without members
How long it takes for a member of Akatsuki to be replaced? Because Itachi appearance was not very different from Part I when he meet Kisame:
Or when he was looking for someone to replace Orochimaru as Sasori's partner:
Strength
This is the most subjective of the points, but nonetheless I think it's valid. How could a 11 years old defeat Orochimaru, one of Konoha strongest Shinobis in Konoha, strong enough to kill a Kazekage and Hokage in the near future?
Not to mention that Itachi would only awaken the Mangekyou Sharingan when Shisui died, days before the Uchiha clan massacre.
And there are several hints that Itachi was not that powerfull during the time of the massacre: Sasuke said he would not be capable of killing all members of the clans by himself; Itachi begged Hiruzen to protect Sasuke from Danzou; Shisui should be as strong if not more than Itachi, and yet somehow he lost an eye to Danzou. Etc.
Conclusion
Orochimaru and Itachi stories don't work together. While they have been members of Akatsuki at the same time, Orochimaru left the organization 7 years before part I, while Itachi joined it at most 5 years before it.
Because Orochimaru was on his 50s, the author used long periods of time for his story, which didn't worked out when it was mixed with Itachi's, who was 18 during his first appearance.
Related: Anko's Cursed Seal and Juugo timeline.
Let's start with Orochimaru timeline. When did he left Konoha? We know he left because Minato was choosen to be Hokage instead of him. It seems he even stayed for a while while Minato was Hokage:
Presumably he left the village prior to the Kyuubi attack. Given that Minato was not a Hokage during Kakashi Gaiden, Orochimaru left the village 12-13 years before Part I.
And it was stated twice that he left Akatsuki 7 years before Part I, or 10 years before Part II:
So Orochimaru stayed in Akatsuki for 7 years at most.
Itachi's age
Now the problem: Orochimaru left Akatsuki because of Itachi, and he was 17-18 years old in Part I.
So Itachi was a member of Akatsuki at age 11... except that he was not. We have seen Itachi when Orochimaru attacked him:
His stature is close to that of an adult like Orochimaru, which was not the case when he was 13 during the Uchiha clan massacre:
And Itachi did not join Akatsuki prior to the massacre. There are two evidences of that, first that his forehead was not crossed at the time:
And second that he only meet Tobi around the time of the massacre:
Akatsuki without members
How long it takes for a member of Akatsuki to be replaced? Because Itachi appearance was not very different from Part I when he meet Kisame:
Or when he was looking for someone to replace Orochimaru as Sasori's partner:
Strength
This is the most subjective of the points, but nonetheless I think it's valid. How could a 11 years old defeat Orochimaru, one of Konoha strongest Shinobis in Konoha, strong enough to kill a Kazekage and Hokage in the near future?
Not to mention that Itachi would only awaken the Mangekyou Sharingan when Shisui died, days before the Uchiha clan massacre.
And there are several hints that Itachi was not that powerfull during the time of the massacre: Sasuke said he would not be capable of killing all members of the clans by himself; Itachi begged Hiruzen to protect Sasuke from Danzou; Shisui should be as strong if not more than Itachi, and yet somehow he lost an eye to Danzou. Etc.
Conclusion
Orochimaru and Itachi stories don't work together. While they have been members of Akatsuki at the same time, Orochimaru left the organization 7 years before part I, while Itachi joined it at most 5 years before it.
Because Orochimaru was on his 50s, the author used long periods of time for his story, which didn't worked out when it was mixed with Itachi's, who was 18 during his first appearance.
Related: Anko's Cursed Seal and Juugo timeline.
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