First Manga Appearance: Chapter 281
First Anime Appearance: Shippuuden Episode 1
Name Meaning: Extreme, Genius, Planting, Loan, Rhinoceros, Companion, a weapon, Son, Navel, Smash, Fine
Character Study: Introduced as a plain spoken and emotionless spy, Sai has broken out of his shell working alongside Naruto and Sakura. Though his loyalty is to Danzou, he has almost always sided with Naruto in all matters, proving to be a valuable ally.
Post-Timeskip | DB 3
Height: 172.1 cm
Weight: 53.3 kg
Registration ID: 012420
Hidden Village: Leaf
Rank: N/A (ANBU Root)
Team: 7 - Haruno Sakura, Uzumaki Naruto, Hatake Kakashi
Academy Grad Age: 9
Chuunin Exam Age: 10
Jutsu: Choujuu Giga, Shunshin, Sumi Bunshin
Like other members of secretive ANBU Root, the young man known as "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 world. 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 the young man'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 painted.
Naruto moved in close to confront him but Sai mocked Naruto, asking if he even had a penis. This was 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 took the opportunity to comment on how he didn't care for Sakura's looks after she suggested he should be nicer to people. Sakura flew into a rage marking the start of ill feelings between the three.
The new Team Kakashi, under the leadership of ANBU member Yamato, started out for the Grass Country. While on their way Naruto eyed Sai with anger, feeling that Sai was similar to Sasuke but a poor replacement. When he made those feelings known, Sai stated that was fine, as he didn't actually have negative feelings about Naruto. Further adding that he didn't want to be compared to a traitor like Sasuke anyway. Naruto was furious but Sakura held him back. While she smiled to explain their feelings she suddenly slugged Sai, stating he should not add his ill-advised commentary on events he knew little about. Sai offered his surprise that her fake smile had so easily deceived him. He smiled in turn and stated how he once read that smiles, even fake ones, can disarm those around them and help them get out of trouble. Yamato threatened his team with imprisonment to force them to work out their problems. They relented and chose to rest a nearby hotsprings resort.
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. They began to 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 though and become a respected comrade.
Sai continued on missions with Team 7 and began to express himself with emotions, much to Danzou's ire. Sai would hang out with Naruto and Sakura and begin to interact with their friends. During one such meeting, Sai chose to avoid revealing his true feelings to Ino. Based on his dealings with Sakura, Sai thought he should try the reverse approach with women. Instead of being honest he would say the opposite of his true feelings to avoid their wrath. Calling Ino beautiful, Sai had made her blush but at the same time he infuriated the "ugly" Sakura. When Team Ten lost their Jounin leader Sarutobi Asuma, Team 7 was dispatched to assist them track down the Akatsuki responsible for Asuma's death. Sai and Sakura left with Pakkun to assist Shikamaru. They arrived and saw Shikamaru had already taken care of Hidan on his own, causing Sai to reevaluate Shikamaru's abilities. Some time later Sai left with Team 7 again to help track Sasuke again, who was on the hunt for his brother Itachi.
BSS: Before Series Start
ASS: After Series Start
(All dates approximate - There is no official comprehensive timeline)
6 Yrs. BSS - Taken in by ANBU Root as orphan.
6 ~ 5 Yrs. BSS - Meets fellow orphan who will become his "brother", Conditioned to not show emotions
0 - Series Start
3 Yrs. 3 Mo. ASS - Dubbed "Sai" by Danzou and placed on Team Kakashi, Attempts to carry out order to Assassinate Sasuke but has change of mind, Begins to explore his emotions.
3 Yrs. 4 Mo. ASS - Travels with Team Kakashi to track down Hidan and Kakuzu.
3 Yrs. 5 Mo. ASS - Travels with Team Kakashi to track down Sasuke.