First Manga Appearance: Chapter 281
First Anime Appearance: Shippuuden Episode 1
Name Meaning: As kanji can mean: Extreme, genius, planting, loan, rhinoceros, companion, a weapon, son, navel, smash, fine
Hidden Village: Leaf Village
Rank: - (ANBU, At Least Chuunin)
Notable Features: Pale in appearance, insults others, has trouble with his emotions, can bring his paintings alive
Notable Quotes: "Your power... it is weak. Do you even have a penis?"
HISTORY:A young mysterious ninja, Sai became one of Naruto's teammates after the two and a half year time-skip. "Sai" is not actually the ninja's name either, being given that name by ANBU Root leader Danzou.Like other members of Root, Sai was an orphan who was taken in and molded to Root's ideals. That of a emotionless, highly trained killing machine. Early in his life he befriended another Root orphan and the two grew close. Sai eventually thought of him as a brother. Sai was a gifted painter and had an art book which featured his growth as a ninja in one half, and his brother in the other. In the following years Sai's brother died due to an illness, and Sai finished shutting himself off emotionally from the word. During this period he was tasked with many highly ranked missions. These included taking out foreign ninja who posed a problem to Konoha. Danzou was greatly impressed by Sai's skills and remarked he was the strongest of his generation.
Eventually Sai was set to be placed on a squad with Naruto by Danzou. Danzou tasked Sai with a secret mission, to align himself with Orochimaru to smooth the takeover of Konoha by the Sannin. The squad's formal goal was to travel to Hidden Grass to meet Sasori's spy which operated in Orochimaru's camp. Before they left Sai sought to test Naruto by using his Choujuu Giga technique. This technique allowed his ink to come to life and form imitations of the creatures which were painted. Naruto moved in close to attack Sai but Sai mocked Naruto, asking if he even had a penis. A joke which he often lobed towards his "brother" years before. Sai then fled and officially joined the team. Sai met Naruto and Sakura and let them know they were now teammates. He told them he was just testing Naruto, and was not impressed. Sai then also took the opportunity to insult Sakura's looks after she suggested he should be nicer to people.
Sai journey with the new Team 7 to meet Sasori's spy. When Orochimaru and Naruto finished their battle, Sai revealed he wanted to join Orochimaru, providing him with the identities of Konoha's ANBU as proof. He returned with the group to their compound and received additional instructions from his superior Danzou. Danzou planned for Sai to join Orochimaru and spy on him and then assassinate Sasuke, to terminate Orochimaru's next vessel. Team 7 caught up with Sai and demanded to know what he planned. Naruto explained how he would never give up on Sasuke and retrieve him. Sai was surprised by the words and saw a bit of his brother in Naruto. He decided to help them rather than kill Sasuke. He helped them search the compound and he found Sasuke first. Sai told Sasuke he planned to save him but Sasuke would have nothing of it, eventually fleeing with Orochimaru. Sai had managed to regain his team's confidence and become a respected comrade. Sai continued on missions with Team 7 and began to express himself with emotions, much to Danzou's ire.