Sasuke and Sai arc

A member of a now-defunct independent subdivision of ANBU called 'Ne' (¸ù, "Root"), Sai is the codename of a ninja about Naruto's age specialising in artistic ninjutsu and functioning as an undercover agent sent by Danzou to inflitrate Team 7 as Sasuke's replacement. His mission and its objective remains unknown, although Sai has claimed it's started in Chapter 294. While he did successfully become a part of Team 7, he has not quite managed to pull it off inconspicuously. His introduction to Naruto being an attack on him, Shikmaru with Choji followed by an insult to Naruto's strength, questioning if he even has a penis; calling Sakura ugly later does not win him any points with her either. Later, he tops it off by vehemently denouncing Sasuke using quite colorful language




With this, it earned him Naruto's rather emphatic flat-out refusal to accept him as a member of the team, insisting that Team 7's third member is still Sasuke, even when he's gone. Sai also earns a well-aimed power punch from Sakura for bad-mouthing Sasuke. As the story unfolds, Sai admits that he has a problem of showing his emotions (even when his brother died) because he is somehow devoid of his own emotion or thoughts. He values the completion of his ANBU mission more than the safety of his teammates, as shown during training with Naruto, as well as when he ignored Yamato's order to catch an unconscious Sakura who fell from a bridge in Chapter 293.

As far as fighting goes, Sai uses a scroll, brush and ink to draw animals which will jump out of the scroll and attack to his will. He can also use this method to produce a fully flight-capable bird, which he can ride. He also wields a short sword like weapon which he keeps on his back at all times. After the fight between Ky¨±bi Naruto and Orochimaru ends, Sai confronts Orochimaru with a message from Danz¨.

After leaving Yamato's side and deciding not to to save Sakura from falling off of a cliff, Sai watches Naruto and Orochimaru's fight from the cover of the neighboring trees. When Orochimaru eventually repels Naruto, Sai approaches him with a proposition from Danzo. Orochimaru accepts, and Sai accompanies him and Kabuto back to their hideout.

Along the way, Kabuto creates a Sai lookalike and leaves it behind to throw off anyone who may be following them. Once arriving at Orochimaru's hideout, Sai is introduced to Sasuke, who has been training under Orochimaru for the past two and a half years. Sasuke seems indifferent to him, expressing discontent towards Orochimaru instead. When Sai mentions that he might get along better with Sasuke than he did with Naruto, Sasuke fixes him with a stare, startling Sai due to the amount of fear it gave to his emotionless self.

After his meeting with Sasuke, Sai is lead to his own room by Kabuto, who locks Sai in when he leaves. Soon after arriving in the room, Team 7, having put extra precautions into following Sai, arrives and confronts Sai about his defection to Orochimaru. Because he has been caught, Sai divulges the information about his true mission: to ally with Orochimaru on Danzo's behalf so that the two may join forces in destroying Konoha. Disgusted by the ramifications of this plan, Team 7 takes Sai from Orochimaru's lair and restrains him. With Sai out of the way, Team 7 prepares to go looking for Sasuke, hoping to bring him back to Konoha. Sai, however, doubts their success, stating that Sasuke no longer cares about them. Naruto, in response, states that he used to hate Sasuke, but over time he has formed a bond with Sasuke through their shared experiences, and as such he will do whatever it takes to bring Sasuke home. Naruto's dedication to retrieving Sasuke strikes a chord with Sai, who is left without words as a result.

Just as Team 7 is about to leave Sai, Kabuto arrives and releases him, hoping that the two will be able to defeat Naruto, Sakura, and Yamato easier as a team. Before any fighting can begin, however, Sai, moved by Naruto's words and hoping to understand the concept of "bonds" better, helps Yamato immobilize Kabuto. After extracting some information from Kabuto, Naruto and Sai break away from the rest of Team 7 to find Sasuke. While they rest, Sai remarks how Naruto reminds him of his older brother, bringing an actual smile to his face as a result of his brother's memory.

Sai's happiness is short-lived, as Orochimaru soon arrives in an attempt to see where Sai's loyalties really lie. With Naruto's encouragement, Sai leaves the scene with the assignment to find Sasuke ringing in his ears. As Sai searches the numerous rooms of Orochimaru's lair, Naruto is rejoined by Sakura and Yamato, forcing Orochimaru to retreat. As Yamato goes through the belongings Sai left behind, he finds a bingo book that has Sasuke listed as a target, indicating that Sai's actual mission has, from the very start, been to kill Sasuke.

As Team 7 splits up again to catch Sai and stop him from accomplishing his mission, Sai finally finds Sasuke asleep in his room. Sasuke, however, is quick to notice Sai's presence and asks what he wants. Sai responds by saying that he is going to bring Sasuke back to Naruto instead of carrying out his mission, willing to fight to protect the bond that Naruto would give his life to defend. Angered that Sai woke him up for a discussion about bonds, Sasuke attacks Sai, destroying the room and causing a large crater to be left in its place. Team 7, attracted to the scene of the attack, confronts Sai about his actual motives. Upon learning of what Sai was trying to do, Sai is welcomed back into the ranks of Team 7, and the group joins together in an attempt to defeat Sasuke.

As the group surrounds and attacks Sasuke, Sai's attack is the only one that manages to be effective. After Sai is congratulated by Sasuke for this feat, the latter uses his Chidori Current to throw the group back. Uninterested in having a drawn out fight, Sasuke prepares to finish the group with a single attack—Kirin—, though before he can do so Orochimaru and a freed Kabuto arrive to stop him, and the three disappear. Team 7, having failed their mission, return to Konoha. After, however, Sai draws a picture of him and Team 7, titling it, "Friends."

Team 10 sub-arc

As Team 7 recuperates, Sai uses his spare time to read up on relationship skills and gaining people's trust at the Konoha library. As one could expect from someone who learned to communicate with others via a book, Sai initially has problems putting what he read into practice, but Naruto tells him not to worry about being formal. During Team 7's dinner with the members of Team 10, Sai puts what he's learned into practice, though finds little success.

Sai later comes to Team 10's aid in their fight against Akatsuki members Hidan and Kakuzu. Because Shikamaru Nara is separated from the rest of the group, Sai and Sakura are sent as backup for him, though upon arrival they find that Shikamaru has already defeated his opponent. Sai returns with everyone else to Konoha, having not taken part in the battle.

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