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This article is a general overview on the canon character. For more information on this particular character, click here to be directed to the associated page on our mother site.
Sai was an orphan who was recruited into Danzō Shimura's Anbu faction called Root. His original name is unknown since serving in Root, but would assume the name "Sai" upon joining Team Kakashi. During his time in Root, Sai was conditioned to suppress his emotions. This was made more certain when his memories of his adoptive brother, Shin, were wiped away upon the latter's death.
When Sai was placed on Team Kakashi, he found himself in conflict with Naruto and Sakura due to his lack of empathy. He would attempt to "smile" on occasions to make a connection, but Sakura in particular could see through the facade. However, his true motives was to discuss important information with Orochimaru on behalf of Danzō and secretly get close enough to kill Sasuke Uchiha. Sai makes it clear on his stance with Sasuke, noting that he was a rogue ninja who fled Konoha to be with the international criminal, Orochimaru, much to the dismay of Naruto and Sakura. Sai's special-assigned mission proved to be of the utmost importance as he refused to help an unconscious Sakura from falling. Despite this, seeing how far Naruto and Sakura were committed to rescuing Sasuke, Sai becomes more intrigued in their relationship, going to as far as double cross Kabuto and help Team Kakashi in their attempt to take Sasuke back to the village. He would continue to open up his heart and regain more insight on human interactions, though he would often struggle with this early on.