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Itachi in Action

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Itachi was born into the Uchiha clan and was praised by all as the best of his generation - a genius above all others. Even by the standards of the battle-adept Uchiha clan, Itachi's prowess far outshone them. However, not even his family, friends, or teachers could understand him. When he was only four, Itachi had already witnessed countless lives lost due to the Third Great Shinobi World War, which emotionally traumatized him and turned him into a pacifist. At age 7, he graduated from the Ninja Academy at the top of his class after only one year, mastered the Sharingan at age eight, passed the Chūnin Exams at age 10, and became an ANBU Captain at age 13.
He was praised highly by his father, who saw the family's future in Itachi, hence neglecting his youngest son, Sasuke. However, during this time Itachi showed great affection towards his little brother and even encouraged his father to come to the Academy enrollment ceremony for Sasuke, something their father had otherwise forgotten, by saying that he would not go to an important mission that would establish Itachi a place in the ANBU ranks, otherwise.
A young Itachi with his family. From left to right: Fugaku, Sasuke, Mikoto, Itachi.AlienGamerAdded by AlienGamer
When the Uchiha began planning to overthrow Konoha, Itachi, as an ANBU, was tasked with spying on the village. Knowing that a coup d’état would only lead to another Ninja War; Itachi began spying on the Uchiha instead, passing on information to the Third Hokage and the other Konoha elders. During this time he began to act strangely, not attending the clan meetings, speaking out against the clan, and becoming the prime suspect for the murder of his best friend, Shisui Uchiha. Due to this the clan lost hope in Itachi and his father began shifting his focus to Sasuke instead. Meanwhile, the Third's attempts to negotiate a bloodless end to hostilities between the two parties were proving ineffective so, against the Third's wishes, Danzō Shimura and the Konoha Council ordered Itachi to wipe out the Uchiha.
Before the fateful night arrived, Itachi discovered the existence of Madara Uchiha, who was attempting to rekindle the flames of war in Konoha. In return for not attacking Konoha, Itachi offered to help Madara claim vengeance against the Uchiha for turning their backs on him decades earlier; Madara agreed. Itachi slaughtered his entire clan overnight, sparing only Sasuke as Sasuke's life was worth more than the village to Itachi, and he could not follow through with the orders to kill him as well. Instead, he made himself out as a villain, who had killed their innocent family only to test his abilities. By doing so, he wanted Sasuke to take vengeance on him and become a hero to Konoha, thus redeeming the Uchiha name. He tortured Sasuke with his Mangekyō Sharingan and encouraged him to become strong enough to kill him and avenge their family. Hoping that his beloved little brother would someday be powerful enough to kill him, Itachi left the village as a traitor. According to Madara Uchiha, Itachi also had a lover, whom he killed during the Uchiha clan massacre.[4]
Itachi massacres the entire Uchiha clan.Magatama90Added by Magatama90 Knowing that Konoha would still want to eliminate Sasuke, Itachi pleaded with the Third Hokage to keep Sasuke safe. He also threatened Danzō to not harm Sasuke or risk him revealing everything he knew about Konoha's secrets to enemy countries. Sasuke's safety was therefore secured and Itachi returned to his original plan of becoming infamous for his slaughter of the Uchiha clan.
Itachi joined Akatsuki in order to keep an eye on the organization, along with Madara Uchiha, in case either ever acted against Konoha, all the while planning for his death at Sasuke's hands. While a member of Akatsuki, Itachi was approached by Orochimaru, who tried to steal his body to gain the Sharingan. Itachi trapped him in a genjutsu and severed his left hand as punishment, forcing Orochimaru to flee the organization. He was partnered with Kisame Hoshigaki, who he initially greeted with threats after the latter tried to intimidate him. Eventually, they became good partners for sharing a common bond of having betrayed the people closest to them. Sometime after joining Akatsuki and forcing Orochimaru to flee, Itachi helped recruit Deidara, by beating him in battle using only his genjutsu, to which Deidara swore vengeance against Itachi.
At some time, Itachi contracted a fatal illness, to which he kept himself alive through the intake of various medicines, in the hopes of living long enough to die by Sasuke's hands.

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