Part I
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When the two revealed their identities, Itachi and Kisame were quick to battle Asuma and Kurenai after they refused to leave. Despite their high ranks of jōnin, Asuma and Kurenai stood little chance against the two Akatsuki members. However, the arrival of Kakashi managed to keep Asuma and Kurenai from receiving any major injuries. After a short skirmish with Kakashi, Itachi activated his Mangekyō Sharingan and used Tsukuyomi to attack Kakashi's mind and spirit, which afterwards left the latter confined to bed for several days. After Kakashi revealed he had knowledge of Akatsuki, Itachi ordered Kisame to kidnap Kakashi and to kill Asuma and Kurenai. However, Might Guy then showed up, revealing that he had already told the ANBU about the two Akatsuki members' presence. Itachi and Kisame retreated, saying that they didn't want to start a war.
Itachi and Kisame tracked Naruto to a hotel where he was staying with Jiraiya at the time. Uninterested in provoking a Sannin, Itachi used a genjutsu on a pretty woman to draw Jiraiya away from Naruto. Taking the chance, Itachi and Kisame confronted Naruto, although, at the very same moment, Sasuke arrived to seek vengeance on his brother. Itachi handled his brother with ease while Kisame and Naruto watched, although Jiraiya arrived in time to save the two boys, having not fallen for the hypnotized woman's charm as he knew that pretty women did not usually show interest in him.
Jiraiya immediately asked Itachi and Kisame if their real goal was kidnapping Naruto. They confirmed this and Itachi understood that Jiraiya was the one who had told Kakashi about Akatsuki. Although Jiraiya wished to fight them himself and prevent others from getting hurt, he honoured Sasuke's feelings, and allowed him to fight Itachi instead. Itachi, however, only proved Jiraiya wrong in letting Sasuke fight by using his Mangekyō Sharingan on his younger brother, thus reaffirming his need to get stronger. Jiraiya saved Sasuke in time by using the Summoning: Toad Mouth Bind, which transformed the entire hotel hallway into a toad's œsophagus to trap Itachi and Kisame. Despite Jiraiya's claim that no-one had escaped this technique before, the two Akatsuki partners managed to evade capture and death using Itachi's Amaterasu, which left him exhausted.
Although he was actually supposed to capture Naruto, Itachi's only reason for returning to Konoha after the death of the Third Hokage was to remind Danzō and the other two village elders that he was still alive and not to harm his younger brother.
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