Kakashi Hatake
Itachi debuts in Part I after Hiruzen's death, when he uses his infiltration of Konoha to hunt down Naruto Uzumaki as an excuse to secretly check on Sasuke's wellbeing. After engaging with Kakashi Hatake and some of Konoha's forces, he reveals Akatsuki's goal to gather the Jinchuriki which are the people that contained the tailed beasts which there are nine of. Itachi also learns that Naruto is under the protection of Jiraiya and sets up a trap to lure the experienced ninja away to grab the boy. However, as Jiraiya comes to Naruto's aid, Itachi finds himself facing Sasuke and directs his brother back on the path of getting stronger by defeating him before he and Kisame fall back.