Season: 20

Itachi is partnered with Kisame and begins his missions as a member of the Akatsuki. The duo succeeds in recruiting Deidara, so Pain assigns the newly formed team of Deidara and Sasori to hunt down the deserter Orochimaru. Meanwhile, intel comes in about an immortal killer, so Itachi, Konan and Kakuzu head out to the Land of Steam.

Itachi becomes a rogue ninja and joins the Akatsuki. He is welcomed and introduced by Pain and Orochimaru as the ex-Leaf ANBU and the man who massacred his entire clan. Itachi is paired up with a man named Juzo, and their first job together is to fulfill an assassination request in the Land of Water.

Itachi joins the ANBU and is quickly promoted to captain. But he must report directly to Danzo, and is placed as a double agent to observe the Uchiha clan, who are in the midst of planning a coup d’état. With dissatisfaction rising within the clan, the Uchiha ultimately decide to carry out their revolt, and the fateful night approaches.

Itachi accompanies his friend Shisui on a three-part training exercise. The two come across a battle between the Hokage’s ANBU and the Foundation. Itachi is confused by their motives and can't discern which side is right or wrong. But Shisui is unwavering in his determination to stop the fighting.