Shisui planned to use his Kotoamatsukami on the Uchiha commanders to force them to compromise, but Danz took his right eye before he could do so. Shisui handed his remaining eye to Itachi and implored him to safeguard the hamlet and their family name before killing himself in the Naka River, his own choices exhausted. When several Uchihas, who were already suspicious of Itachi, accused him of murdering Shisui and faking a suicide the next day, Itachi lost his cool and fought them, easily beating them.
Itachi and his family were estranged, and his cautions to them to reconsider their actions fell on deaf ears. Itachi went with his brother. Itachi Uchiha consented to carry out the slaughter on the condition that certain conditions be met. Danzo Shimura exploited the fact that Itachi was very protective of his younger brother Sasuke to sweeten the pact.
He stated that if Itachi carried out the attack and took the fall, they would leave Sasuke alive. Itachi was very devoted to Konoha, as seen by his deeds, and took his oath as a village shinobi very seriously. In addition to the possibility that his younger brother might perish, Konoha operatives warned Itachi that if his family was successful, another world war may erupt.
Itachi was determined to prevent this at all costs, and he carried out the heinous scheme. Itachi noticed a masked guy creeping about Konoha while making final preparations. After studying him, he concluded that the guy was really Madara Uchiha, intent on inciting a new battle.
Itachi was an Uchiha Anbu spy who discovered that his own clan was planning a coup that would result in a civil war, weakening the village and making it exposed to outside dangers such as other ambitious villages who would take the chance.
Danzo then informed Itachi that if he killed his whole tribe, his brother would be saved, or he would perish with his kin. This is where Itachi established himself as one of the most stupid and crazy characters in all of Naruto and anime.
The Uchihas were loathed and feared by the community, were pushed to the outside, were looked down upon, and even their leader was treated like garbage like the rest of them. So the Uchiha leader Fugaku grows weary of his clan being treated so poorly by the town and makes it his mission to put a stop to it so that the Uchihas are no longer oppressed and looked down upon in perpetuity.
He plots a coup to depose the village leaders so that he may become Hokage and liberate his people. What did Itachi do to put a stop to the coup? He killed his whole tribe women, men, and children with his plus one. At this point, however, Itachi is already a spy for the village advisor Danzo. With his double-agent status, Itachi believed that he was aiding the cause for peace.
Danzo believed that, if left unchecked, the Uchihas would incite another war. Itachi informed Danzo of his family's coup plans, and Danzo manipulated Itachi into believing that the coup could not be stopped without bloodshed. He stole Shisui's eye, which led Itachi to become conflicted about who he could trust. Ultimately Danzo played on Itachi's trauma and naivete to manipulate him into killing the Uchiha clan. Itachi hoped to prevent another Shiboi war and the loss of many innocent lives.
Itachi led Sasuke, the brother he spared, on a course for revenge and vengeance. He believed only Sasuke could pass judgment on him for the massacre that he had committed, and wanted his brother Sasuke to get strong enough to slay him. Unfortunately, Itachi's attempts to broker peace failed, and after the death of his close friend Shisui, he became convinced that peace was no longer an option.
Even after accepting that the Uchiha coup was inevitable, Itachi wasn't hellbent on fighting them. It wasn't until Danzo offered Itachi the mother of all ultimatums that he agreed to become a villain. He could either die along with the rest of his clan at the hands of the Leaf Village, or he could do the dirty deed himself, sparing only his younger brother, and walk away alive. As we already know, Itachi took this deal. A lot happens during Itachi's massacre, but the gist is that Itachi performs his duty relentlessly and without mercy.
As a shinobi prodigy, Itachi stood as one of the Village's strongest soldiers even as a kid. When he happens upon his parents, the two submit and allow him to kill them. They know why Itachi has agreed to kill his clan, and they are proud of him despite their differences.
Sasuke appears, and witnesses the death of his parents before Itachi leaves, encouraging him to get stronger and seek revenge. Itachi expected Fugaku to be the greatest enemy and entered his home with great caution. To his complete surprise, both his parents were willing to accept death rather than fight their son. Both respected his decision to side with the village over the clan, and asked only that he look after Sasuke. He tearfully killed them just before Sasuke returned home from the Academy.
Although he knew his actions were necessary, Itachi could not forgive himself for killing his own family and believed he had to be punished. Sasuke, a child and thus ignorant of the Uchiha's conspiracies, was the only person qualified to pass the judgement on Itachi he felt he deserved. As such, Itachi attacked Sasuke when he entered their house, desperate to make Sasuke believe he had killed their clan without provocation and for selfish pursuits of power.
He used Tsukuyomi to torment Sasuke with images of the clan's murder and claimed Sasuke was too weak to even bother killing. Itachi encouraged Sasuke to embrace hatred and vengeance in order to get stronger and to come after and kill him to avenge their family. As Itachi left, Sasuke made an immediate attempt to follow Itachi's instructions; awakening his Sharingan for the first time, Sasuke pursued Itachi and attacked him, managing to knock off his forehead protector.
Itachi wept from Sasuke's action, but continued on after collecting his forehead protector. Sasuke passed out from the traumas of the night and would not remember this moment of retaliation for many years. Only three Uchiha survived the clan's massacre: Itachi, Sasuke, and Tobi, though most of the world, Sasuke included, did not know of Tobi's involvement in the massacre or survival.
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