Naruto Timeline Weirdness

[H-Man]

It's involved.

 

[Knyght]

Orochimaru leaving Akatsuki

Orochimaru is said to have left Akatsuki 7 years before the timeskip. He left because he was defeated by Itachi who was a member at the time but Itachi would have only been 11 years old at the time. Yet he was able to defeat Orochimaru effortlessly, looked far older than a pre-teen and was shown as a member of Akatsuki even though it was 2 years before the Uchiha Massacre and his flight from the village.

FYI, Itachi became a chuunin at 10, joined ANBU half a year later, and became ANBU Captain at 13.

He should have killed Orochimaru after leaving Konoha at 13-14 years old.

I've just been reminded that the fourth databook retconned Orochimaru's defection by saying that his fight with Itachi took place 7 years before the end of the Fourth Shinobi World War instead of 7 years before Part 1. Making Itachi 15 years old at the time and resolves the contradiction, I believe.