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Itachi Awakened his Sharingan at the Age of 6 or less
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Here is my theory.
It is stated here that Itachi could use his sharingan at the age of 8.
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Itachi was said to be thinking like a Hokage at the age of 7, something that occurred as the result of the war around him at that age (The violence beginning at age four and ending at age five or six).
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Obito clearly states here that trauma of the war caused him to hate warfare.
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As many of you know the Uchiha's Sharingan is awakened by a traumatic event.
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There are no notable tragedies and/or acts of warfare in Konohagakure from the end of the Third Shinobi World War until the Nine-Tails Attack on Konohagakure.
The next attack would be roughly 13 years later, when Sunagakure attacked Konohagakure through Orochimaru's manipulation.
Third Shinobi World War
Since we don't know of any other emotional events that would have awakened his sharingan, it is most reasonable to believe he awakened his sharingan before he had come as far as reasoning at such a high level (ate age 7); seeing that the trauma of the war most likely influenced these new ways of thinking in Itachi.
(During the Third Ninja War or shortly after it he awakened his sharingan, and adopted advanced philosophies for his age.)
Nine Tails Attack on Konoha
If these tragedies did not cause Itachi to awaken his sharingan then the last thing that would have triggered them would be the attack on Konohagakure, which Itachi holds so deeply in his heart.
Here we can see that Itachi was present during that time.
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Because sasuke was an infant, (no older than 1 year of age) Itachi would have been at the age of five or possibly six. It is possible that by seeing ( Or hearing) his beloved village crushed and destroyed (Massive damage to the village structures, the sounds of screams echoing in the night) that he awakened his sharingan.
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Conclusion
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