Yamanaka Sai

Sai (サイ) is an ANBU-level shinobi of Konohagakure and is from the disbanded faction: Root. He later became a major supporting characters of the series, and is a member of Team Kakashi, having to replace Uchiha Sasuke.

Background
Sai was orphaned as a child and recruited into Root, a secret branch of the ANBU. There he was raised and conditioned to have no personality, personal connections, or a name; "Sai" being given to him for the purposes of joining Team Kakashi. Though largely successful in this regard, Sai retained an interest in art. When Shin, an older Root member, discovered Sai's drawing ability, he encouraged Sai's talent and they became very close.

Over time, Sai came to think of Shin as an older brother and looked up to him. Unfortunately, Sai and Shin were supposed to fight to the death by Root regulations, in a final step to eradicate emotions. Before that happened, however, Shin died of an unnamed illness and Sai's Root training suppressed most of the memories he had of him. In the anime, Sai and Shin were forced to fight by Danzō Shimura but Shin died before the battle could be finished. Shin told Sai to report to Danzō that he killed him in battle and before succumbing to his illness, told his brother that he had to suppress his feelings and that he should live for the both of them.

Before Shin's death, Sai created a picture book that would depict all the opponents they faced and illustrate the feelings that they shared for each other. Sai organised the book so that his and Shin's portraits would be located at opposite ends of the book, and in the centre pages would be a picture of them holding hands. Some time after the loss of Shin, Sai forgot that this was his intention, and the picture book was left unfinished, though he could never bring it upon himself to discard the book. But after bonding with Uzumaki Naruto, Sai remembers and completes the book, causing him to give his first genuine display of emotion in a long time: a smile.

Before his appointment to Team Kakashi, Sai — under Root's orders — had been eliminating individuals that worked against Konoha. The last assassination he performed was of Unmo Samidare.[5] In an attempt to gain a powerful fūinjutsu after seeing the Third Hokage sacrifice his life in an attempt to defeat Orochimaru, Danzō supervised Sai while he learned how to use the Sealing Technique: Tiger Vision Staring Bullet, noting that it would be dangerous as he would have to use "emotional energy" in order to make the technique stronger. Sai struggled greatly with this endeavour as it conflicted with his training and, consumed by negative emotions, his training was seemingly left incomplete.

Personality
When first introduced, Sai was distinguished by his total lack of emotion which he often masks with a false, cheerful, yet transparent façade. After much mental conditioning and training while in Root, Sai had suppressed almost all of his emotions, laying all of his loyalty to whoever commands him, and thus making it easier for him to accomplish dangerous, unpleasant, or unethical missions. Due to this training and his lack of social experience and personal initiative, Sai has great trouble in understanding how bonds between people can motivate others. He often showcases this confusion after thinking about why Naruto would go so far to save Sasuke, a traitor, even though Naruto had not been ordered to do so.

Sai's social awkwardness tended to get people angry, because he would often speak without considering his words and their effects on people. This was due to his inability to realise the difference between a rude statement and a true statement. Sai had read somewhere in a book that giving somebody a nickname would bring you closer to that person and develop your friendship, this resulted in Sai hurting Haruno Sakura's feelings, because he called her ugly, stating the first true character trait that came to his mind. This also nearly led to enraging Choji, while eating barbecue with Team Asuma and Team Kakashi he nearly called him "fatso". Luckily Naruto covered his mouth before he could finish.

After spending more time with Team Kakashi, Sai comes to appreciate bonds, particularly the bond that exists between Naruto Uzumaki and Sasuke Uchiha, though Sai would come to have his doubts Sasuke when he began to commits crimes on an international scale, which Naruto would suffer for. This causes him to break out of his emotionless shell and he starts to remember the times he had with his own "brother", Shin. In doing so, Sai was able to start giving genuine smiles. Wanting to experience personal bonds for himself, Sai sets out to make as many friends as he can. However, since he is learning most of this out of books and by trial and error, he often accidentally ends up offending people with his nicknames and conversation. He has come to develop a more genuine, pleasant and thoughtful personality, while also showing signs of more emotion, such as enthusiasm and occasionally nervousness.

After his first time with Team Kakashi, Sai is seen being friendly towards others, helping companions when they need it, referring to peers kindly, and having fun in social situations. The greatest change in his personality, however, came after he encounters his reincarnated brother. When Shin is used as a living bomb by Deidara, Sai becomes enraged and attacks Sasori and Deidara mercilessly, showing genuine rage on his face. Sai also displays genuine sadness, shedding tears when his brother is freed from the technique and disappears.

Sai is very observant, and is always focused on his missions. He pays a lot of attention to detail, allowing him to quickly notice if something is not as it appears, as shown from how he easily sees through Yamato's tricks. This awareness spans beyond the trials of duty, as Sai was later quick to understand the nature of Naruto's inner burden. What he failed to understand, however, was that Naruto was not trying to save Sasuke just for Sakura. Sai holds Naruto in high regard, and tries to assist Naruto whenever he's going through hardships.

Appearance
Sai has short, black hair, and black eyes which contrast with his very pale skin. He is usually seen carrying a small backpack with his brush, scrolls, and ninja ink in it. He wears a short black jacket with red straps — as customary of all Root members, to most likely show his allegiance to the organisation. He also carries a tip-less tanto on his back. The rest of his outfit consisted of a high-collared midriff shirt, black pants, shinobi sandals and gloves with his index and thumb fingers exposed, most likely to facilitate the use of his drawing based techniques. When first seen with Team Kakashi, his jacket has a long right and short left sleeves. He had Danzo's cursed seal on the back of his tongue until Danzo's death, which caused it to disappear. Naruto, Sakura, and Ino said he physically resembled Sasuke, despite his shorter hair and paler skin-tone.

When he's not on missions, Sai wears a casual outfit consisting of a long-sleeve shirt with a high collar, matching pants, and his regular shinobi sandals. This outfit was first depicted as being purple in colour and later, navy blue. He doesn't wear his forehead protector or gloves with this outfit.

In the anime, when Sai uses the Sealing Technique: Tiger Vision Staring Bullet and his negative emotions surface because of his use of "emotional energy", his eyes turn a translucent red colour and his sclerae turn black. This is apparently, as when Danzō countered the symptoms, ink splattered from Sai's body.

Abilities
As a member of Root, Sai is a highly capable ninja, considered by Danzo himself to be the strongest member of his generation. Danzo even had enough faith in Sai's abilities to task him with single-handedly killing Uchiha Sasuke. As a Root ANBU, Sai has keen observation skills and is also skilled in kenjutsu and wields a tanto in battle.

Ink Techniques
Sai's most knownble talent is his skill as an artist, and he claims to have drawn thousands of pictures. Despite the great quantity and magnitude of the things he has drawn, he has never given any of his works a name, his lack of emotion making it impossible for him to form a significant enough attachment to his art to give titles. Even so, Sai's drawing talent is also the source of his technique, known as Super Beast Imitating Drawing.

To be able to execute his Super Beast Imitation Drawing technique, Sai carries around a specialised custom scroll to draw on, the scroll's roller has compartments for Sai's ink brush and to hold a supply of ink. A distinct advantage of this technique is that he can perform it with a single hand, leaving the other free for enemy counter-attacks. In the anime, Sai gets his ink from a supply store, which he says is the ink that works best for his Super Beast Imitation Drawing techniques. By infusing his chakra into the ink beforehand and drawing objects with a brush on his scroll, which he can do very quickly, Sai is able to bring his creations to life by animating the ink directly off the page. These creations grow to life-size once they have been brought to life — similar to Deidara's explosive clay constructs.

Sai typically creates giant birds for long range transport for himself or others, and lion-like monsters or giants for attack, or objects like umbrellas for everyday use. He can create snakes and use them as strong bindings on enemies, or mice to quickly scout an area. Sai can make clones of himself for reconnaissance. For discreet communiques when he is undercover, Sai is able to turn the words he writes into small animals, allowing them to travel to their intended target unnoticed. He has also demonstrated the ability to create large scale drawings as shown during the battle of the two ambush squads; he created two large human beings which resembled the Benevolent Kings (仁王, Niō). These had enough physical strength to completely destroy Deidara's clay bird as well as send him along with Sasori plummeting to the ground. Sai can create explosive tags with his ink technique. He can draw long lines of tags attached to small birds, allowing him to bombard enemies from the air.

As noted by Kakashi, Sai is one of Danzō's prized soldiers and as such, his Root training also included learning fūinjutsu. His sealing technique allows him to trap people within his paintings by drawing a tiger on a large scroll with a giant paint brush. Since it takes time to draw the tiger, he needs allies to protect him while in battle. In the anime, it is stated that Sai uses "emotional energy" to bolster the technique. This is a double-edged sword as Sai becomes susceptible to his negative emotions.

Taijutsu
Despite not being his speciality, Sai has shown to be proficient in taijutsu. He was able to react and block Naruto's attempt to stab him with a kunai very easily with his tanto. He also was able to subdue Kabuto Yakushi very easily and block Sasuke's attempt to stab Naruto, with Sasuke commenting that he blocked the attack in the most appropriate manner. During the Fourth Shinobi War, he was able to break Shin's neck with a flying knee kick in mid-air.

He is also very proficient with the Body Flicker Technique, and is capable of surprising even highly-skilled shinobi with it.

Sasuke & Sai arc
Sai was assigned to join Team Kakashi by his superior Danzō to assist in meeting with a spy in Orochimaru's ranks to find out about Sasuke Uchiha. Sai was confrontational with his new team-mates upon their first meeting, exasperated both Sakura and Naruto. On their way to the rendezvous point, Sai once again aggravated them, questioning Naruto's manhood and insulting Sasuke. The latter caused Sakura Haruno to punch him in anger. As they continued on to the meeting point, Sai questioned why Naruto was loyal to a traitor like Sasuke, to which Naruto stated he was not a traitor, but a friend.

Upon reaching the designated meeting place, Yamato went ahead disguised as Sasori so that he could meet the spy. When the spy, Kabuto Yakushi, arrived with Orochimaru to kill Sasori, Sai, Naruto, and Sakura were called in for help. When Naruto and Orochimaru began fighting, Sai left the rest of the team to begin his real mission. He briefly observed Naruto's fight with Orochimaru, unconcerned with the danger he left Yamato and Sakura in, and approached Orochimaru after he had repelled Naruto with a proposition from Danzō. Orochimaru accepted, and Sai accompanied him and Kabuto back to their hideout.

Once arrived at Orochimaru's hideout, Sai was introduced to Sasuke, who had been training under Orochimaru for the past two-and-a-half years. When Sai mentioned that he might get along better with Sasuke than he did Naruto, Sasuke fixed him with a stare, startling Sai due to the amount of fear it gave his emotionless self. He was led to his own room afterwards by Kabuto, who locked Sai in upon leaving. Soon afterwards, Team Kakashi tracked Sai down and confronted him about his real mission. Having been caught, Sai explained that he had been assigned to ally with Orochimaru on Danzō's behalf so that the two may join forces in destroying Konohagakure.

Disgusted by the ramifications of this plan, Team Kakashi restrained Sai before setting out to find and retrieve Sasuke. Sai, however, doubted their success, stating that Sasuke no longer cared about them. Naruto, in response, stated that he also used to hate Sasuke, but over time he had formed a bond with Sasuke through their shared experiences, and as such he would do whatever it took to bring Sasuke home. Naruto's dedication to retrieving Sasuke struck a chord with Sai, who was left without words as a result. When Kabuto arrived and freed Sai, Sai instead helped them capturing Kabuto, hoping to accompany Naruto to find out more about bonds.

Naruto and Sai split away from Sakura and Yamato to go looking for Sasuke. They were soon found by Orochimaru, and as a result, Naruto distracted him so that Sai could have a chance to scout on ahead. When Orochimaru retreated and Naruto reunited with Sakura and Yamato, Yamato went through the belongings that Sai had left behind. In doing so he discovered Sai's actual mission: to kill Sasuke as a traitor to Konoha. Team Kakashi raced through the base to find and stop Sai, but Sai had already found Sasuke. Sai, however, truly had a change of heart, and instead, tried to capture Sasuke in order to protect his bond with Naruto.

Irritated by Sai's reasons for bothering him, Sasuke attacked Sai, drawing the rest of the team to their location. When they found out what Sai was trying to do, they all teamed up to restrain Sasuke. Although Sai was able to land a successful attack, Sasuke's abilities were too much for them and he prepared to kill them all. He was soon stopped by Orochimaru and Kabuto, who convinced him to spare the team before leaving. Defeated, Team Kakashi returned home. Sai requested that he be allowed to stay as a part of the team and, with Danzō's approval, began to spend time with his new friends.

Twelve Guardians arc
At one point, Sai began to visit the Konoha library to read about relationships in the hopes of making some for himself. In the anime, this had begun before and continued throughout the Twelve Guardian Ninja Arc. When he read that nicknames were a good way to make friends, Sai made the mistake of using nicknames that describe how he actually saw a person. When calling Sakura "ugly" earned him a beating, he concluded that women liked to be called the opposite of what was true. To that end, he called Yamanaka Ino "beautiful", something that got him another beating from Sakura.

Sai, Yamato, Naruto, and Sakura were sent on a mission near the Fire Temple. When the party didn't meet the group, they decided to split up to find them. After grouping with Yamato, Sakura and the monks, Sai saw Sora, a monk in training, fighting Naruto who also appeared to have wind release. This turned out to be a misunderstanding on the behalf of Sora thinking Naruto was trying to invade the temple.

After clearing up the confusion, the monks lead Team Kakashi to the Fire Temple. Upon reaching the temple, the monks explained to the team the situation regarding the sacred tombs' mysterious disappearance. After seeing Naruto and Sora bickering, they headed off only to return to the temple hearing news that another tomb was robbed. Soon after that, Team Kakashi, accompanied by Chiriku and Sora, moved out to find the perpetrators. They soon spotted four other tombs moving across a field by themselves. They found that the tombs were heading up a cliff where four ninja named Furido, Fudō, Fūka, and Fuen were. Fudō quickly used earth release to create a rocky canyon maze, which separated Team Kakashi and Sora. Sai tried to escape by using a ink bird but, unfortunately, got sealed up. He along with the others were confronted by the ninja. He was confronted by Fuen who mocked him for not being able to escape. Sai, awared that the enemy knew the area, attempted to leave and plan. Though he did get away, the enemy had the blue prints to the area knew exactly where he went off to and tried to kill him.

He later saved Sakura from a a giant spider. He was able to kill it only to get his arm broken in the process. Sakura tended to his wound. After the two had met up with Yamato, they found Naruto being drained off his chakra by a kiss from Fuka. They tried to help but got trapped by Fuen and Fudo. After the the area caved in, they all got away. It was soon figured out that they might be after Sora. When the group returned to the village, Sora went with them. While Sai left to take a rest, Naruto introduced Sora around the village per Sakura's request. Later, Sai, from the hospital, saw that the village was being attacked by a jutsu used by Fudo and his fellow members. He later snuck out of the hospital to help Asuma fight Kazuma. After Kazuma is defeat,Sai is seen with the rest of his friends. Sai asks Naruto if he can join in on the conversation,but Naruto says no.

Hidan & Kakuzu arc
Sai and the rest of team Kakashi were later sent as backup for Team 10 during their battle with the Akatsuki. Because Shikamaru was separated from the rest of the group, Sai and Sakura were sent to his aid, though upon arrival they found that Shikamaru had already defeated his opponent. Sai returned with everyone else to Konoha, having not taken part in the battle. Because Naruto was injured during the battle, he has difficulty eating when they got back. Sai, wanting to ameliorate their friendship, attempted to feed Naruto which angered him since he had wanted Sakura to feed him and Sai had interrupted her doing so. Neither has their way as Kakashi himself took up the task of feeding Naruto instead.

Three Tails arc
Sai was placed on Team One along with Kakashi, Shino, and Naruto. His team's duty was to fight any enemies who closed into the area so they wouldn't disrupt the sealing process. After he had introduced himself to Shino, he found that Shino had a bit of a grudge towards Naruto, since it turned out that though Sai only knew Naruto for a few months, he knew much about him, in fact more than he did. Also, he was reminded how Naruto didn't recognise him when he returned from the Kazekage Rescue mission.

Sai's team ran into Guren and Gozu. Sai was soon put the battle Gozu who proved to be quite capable in fighting. Sai tried restraining him with ink snakes but he eventually broke free. He also tried holding his ground by deflecting some of Guren's crystal shuriken with his tantō. At some point while the Konoha took a break from trying to seal the beast after failing, he was punched by Sakura and Ino. He mistakenly got in between their bickering and overheard nicknames they called each other, thinking it'd be okay to repeat. Those being "Forehead Girl" and "Ino-pig".

Itachi Pursuit arc
Along with Team Kurenai, Sai and the rest of Team Kakashi set out to find and capture Uchiha Itachi. When Kakashi summoned his ninken to assist them on the mission, Sai was partnered with Ūhei and Urushi and wondered to himself whether or not he could become friends with dogs. He and the others were later confronted by Tobi, who stalled them long enough to prevent them from locating neither Sasuke nor Itachi. As soon as they got to Sasuke's location,no one was there. The mission became a failure, and everyone returned to Konoha.

Tsuchigumo Kinjutsu arc
Team Kakashi are assigned by Tsunade to go and protect Hotaru on her way to the Tsuchigumo village. When the team find the fort, they saw Tonbee, who has been viciously attacked by the four-man bandits. Sakura stays and heals Tonbee, while Naruto, Sai, and Yamato follow Utakata and Hotaru. Naruto catches up to Utakata and Hotaru, and Utakata attacks Naruto with some of his Soap Bubble Ninjutsu. After Utakata learned that they are not attackers, he entrusts the protection of Hotaru to them.

In the next episode, we see some scenes of Utakata's past, including a vision of his master attempting to draw out his tailed beast. Hotaru refuses to let the Konoha ninja escort her to the Tsuchigumo clan's secret village. Sai then tricks her into thinking that giant leeches are falling on her and she begs Naruto for protection. When they reach the hidden village, Naruto leaves the village with a suspicious feeling because of the way that the villagers looked at Hotaru. Utakata also starts fighting the Magaki Group, and starts to gain the upper hand easily, but then they trap him in a Lightning Release barrier that implodes.

On the third episode of the series, we see Hotaru's uncle betraying her to the Magaki Group, but when they think that they have found the hidden scroll, it turns out to be a bomb. Hotaru escapes, and she meets up with Utakata in the forest. He faces off against the bandits again, and quickly flees.

After Utakata escaped with Hotaru, the bandits were confronted by their leader, Shiranami. He showed them that Utakata was a missing-nin from Kirigakure with a bounty of 50 million ryō. Akaboshi asked their leader what they should do, which he began to muse about.

When Hotaru and Utakata were alone, Utakata was about to leave Hotaru again, but Hotaru, trying to convince him not to leave her alone, partially took off her shirt, showing him something on her back that shocked him.

All of a sudden, the Kirigakure ANBU found Utakata and wrapped him up with their Water Release: Water Whip technique and began subduing him with their Lightning Release: Electromagnetic Murder. The captain revealed to Hotaru, who he was holding hostage, that Utakata was in their Bingo Book, and was wanted for killing his master. Naruto and his team arrived and managed to loosen one of the water whips holding Utakata. Both parties began to fight, but the leader of the Kirigakure ANBU appeared, and discussed the situation with Yamato. Due to Hotaru's insistence to be with Utakata, it was agreed that Utakata stayed with Team Yamato and they wouldn't hunt him until she was safe, but afterwards, they'd resume tracking Utakata down. Tsurugi, the leader, asked Utakata to return to Kirigakure, saying that the village changed, no longer earning the nickname of Village of the Bloody Mist. Utakata refuses, and says that he'll keep doing as he pleases.

After the groups part ways, Hotaru begins hurting from an injury sustained during the earlier altercation. Utakata has Naruto collect medicinal herbs. When Naruto returns, he witnesses what was done to Hotaru's back, where her clan's kinjutsu was put. Utakata voices his absolute disdain for people who selfishly take advantage of people's loyalty, only to treat them as tools.

Everyone is shocked to learned that Hotaru actually requested for the technique to be sealed in her. After she explained that she wanted her grandfather's dream to restore their clan's glory to come true. When Tonbee voiced his sorrow that by now the clan had probably lost too much strength to ever return to such a status he suggested they end the potential danger of the kinjutsu by destroying it. Utakata was surprised that Hotaru's grandfather had created a way to safely remove it from Hotaru's body. When Tonbee insisted that no true master would do such horrific things without a way to undo them, Utakata wondered if the same was true for his master. Utakata resolved to find Tsurugi again to learn some answers about his late master.

Hotaru initially refused the idea to destroy the kinjutsu, feeling that it would make all her grandfather's efforts for nothing, but Utakata made her see that she couldn't restore their clan with such a destructive technique. While willing to accept this decision as a final act, she offered one other possible solution, to search for a man named Shiranami, who is an immensely gifted ninja who studied En no Gyōja's teachings and could be of great help. It was then decided that Naruto would attempt to find the man in two days while preparations for removing the kinjutsu were made.

When Naruto Uzumaki sought out Shiranami, the Magaki leader, who believed the latter was an ally, the Magaki Group ambushed Naruto and used Infinite Embrace to drain his chakra. While Chūshin beat Naruto, Benten almost revealed their plan before Akaboshi silenced him. Angered at being deceived, Naruto unleashed the Nine-Tails' chakra and broke out of the Infinite Embrace. Though shocked at Naruto's strength, the Magaki used their Multiple Infinite Embraces to crush Naruto. Much to their shock, however, Naruto was still able to resist, but not for long.

Later to Hotaru's dismay, Utakata suddenly leaves. Not wanting him to leave her, Hotaru goes off to find him. Along the way, she runs into Shiranami himself. He sympathises with Hotaru's loneliness and desire to restore their clan. After being convinced not to destroy the technique, she decides to write a message to Utakata. However, Shiranami reveals his true colours and knocks out Hotaru, taking her back to the Tsuchigumo village.

When Utakata is unable to find Tsurugi he finds Hotaru's messenger bird with a note for him. While it is from Hotaru saying she found Shiranami, Utakata is still at unease, feeling something is wrong. He goes to the location Hotaru wrote and finds that Shiranami is actually the leader of the bandits who trapped Naruto in a fūinjutsu. Utakata then uses his tailed beast chakra to scare the bandits and make them run.

Afterwards, he and Naruto track Shiranami back to Hotaru's village, where it is discovered that Shiranami took control of the villagers with his technique. The villagers attacked Utakata and Naruto and they were also confronted by the Magaki Group. Just before things got worse, the rest of Team Yamato arrived while hunting for Hotaru. Yamato, Sai and Sakura were fighting the villagers and the Magaki Group, while Naruto and Utakata were trying to save Hotaru from Shiranami. In the end Naruto and Utakata manage to save Hotaru and Team Yamato parts ways with Hotaru and Utakata.

Invasion of Pain arc
When Naruto entered the Hokage's office, he was seen with Sakura, the toads, Shizune and the Hokage as Naruto learnt of his master's demise. During the invasion of Pain, Sai was away with Yamato and Mitarashi Anko, tracking down Kabuto Yakushi. He used a special tracking technique that could not be detected by Kabuto. Anko even congratulated him for that. They stopped the search just after a surprised Yamato had informed the group that Naruto had reached the six-tailed form of the Nine-Tails.

Five Kage Summit arc
After the invasion, Danzo is made Hokage. He summoned Sai before him and instructed him to keep an eye on Naruto. Sai asked why, so Danzo explained that Naruto, having defeated Pain, was now the village's hero and thus more popular than Danzo himself. However, he was still the village's jinchuriki and therefore must be kept in check. Sai was satisfied with his explanation and went to meet with Naruto and Sakura. The two immediately confronted him about Danzo, asking him to tell them everything he knew. Sai said that he could not, as the cursed seal Danzō had placed on his tongue prevented him from revealing anything about Root. Sakura remarked it was cruel, but Sai explained that it was for the best since Root had done a number of questionable things to protect the village.

Sakura refuted his claim, pointing out that Danzō had ordered Sasuke be killed as a traitor. Sai was surprised since Danzō had not told him that during their meeting. They were immediately confronted by Kumogakure ninja who, after their brief skirmish, demand to know what they knew about Sasuke. Naruto, seeing that this upsetted Sakura, volunteered to tell them all that he knew. Sai secretly watched the meeting and how Naruto could not bring himself to sell out Sasuke.

Naruto allowed Karui to take out her anger on him. Karui happily accepted and proceed to beat him up, but Sai stepped in once she started to overdo it. When Karui left, Sai brought Naruto to Kakashi and Yamato and then tended to his wounds. Naruto asked that Kakashi and Yamato help him find the Fourth Raikage. When they had agreed, Kakashi told Sai not to tell Danzō what Naruto was doing. After hearing such a request Sai looked rather upset and asked Kakashi if he didn't trust him because he was from Root, but Kakashi answered that he believed in him because he was also a member of Team Kakashi. Hearing these words made Sai happy and drove him to act more resolutely. Sai later approached Sakura, telling her about what Naruto had gone through with Karui for her benefit. He surmised that Naruto deeply loved Sakura, and that trying to make her happy, such as bringing Sasuke back to the village, caused him constant pain.

Following the Konoha 11's decision to eliminate Sasuke themselves to prevent a war, Sakura asked Sai to help her track down Naruto so that she could speak with him. They found him in the Land of Iron and Sakura confessed her love to Naruto, so now he didn't need to bother fulfilling his promise of retrieving Sasuke. When Naruto didn't believe her, Sakura left with her group. Because she didn't mention the decision to kill Sasuke and that he felt responsible for what she was about to do because of what he had told her back in Konoha, he left an ink clone behind to tell them what Sakura had not. The clone also added that Sakura was likely planning to kill Sasuke personally, and mentioned that Sakura was still in love with Sasuke and wanted to stop him from sinking any lower.

The ink clone helped Kakashi locate Sakura. The real Sai, meanwhile, stopped Sakura from knocking him out and her other escorts, having suspected that she would try to get rid of them so she could fight Sasuke alone. Sakura convinced Kiba and Lee that Sai was a traitor and they started to fight him, but this only made it easier for her to knock out all three. As the ink clone dispersed it warned Kakashi of Sakura's actions. Sai and the others were later woken following the meeting with Sasuke, and as they return to the village they were met by three Root members. They inquired about what had happened. Sai affirmed that the seal disappearing was proof that Danzo had died. He then encouraged them to speak with Kakashi whom he addressed as the "new Hokage" about Root's future.

Chikara arc
The reborn Team Kakashi is sent out on a mission by Tsunade to a location known as "The Hole" to investigate an incident where Tonika Village's people had been killed. Regretting that she could not assign more people to the mission because of recent incidents elsewhere, the team sets out nonetheless. While there, they split up into two man teams, with Sai encountering officers from the neighbouring Hachō Village, consisting of Shiseru and her team. After finding out who the Konoha shinobi were, the officers escort them to their village leader, Disonasu. Elsewhere, Sakura and Naruto, who are at The Hole's water spring, encounter Kabuto Yakushi, who uses tiny, specially-created snakes to create a clone of Hidan using his DNA and the water of The Hole, which possesses special properties. Kabuto then reveals that he had reincarnated several shinobi. A fight ensues between the two sides as Yamato and Sai rejoin with their team-mates.

As Team Kakashi continues to battle Kabuto, Hidan and the reincarnated shinobi, Naruto gets swallowed by a giant snake created by Kabuto, but manages to escape using shadow clones, accidentally ingesting Kabuto's clone snakes in the process. When Naruto resurfaces, Kabuto retreats, using the reincarnated Deidara as a diversion, after revealing a village guard's corpse in the mouth of a snake. Meanwhile, Dokku takes care of the orphans, while Miina, due to trauma, becomes mute. After the attack, Naruto and Sakura join up with Shiseru, Yamato and Sai in going with the rest of the guards. While Yamato and Sai investigate Kabuto's motive for destroying the village, Sakura and Naruto follow Shiseru to Dokku's house. When Dokku and the orphans see them, noticing that Naruto wears the same forehead protector as the reincarnated shinobi, Leo kicks Naruto and they run until they reach a broken bridge. Leo crosses first and when Dokku and Miina run, they fall down the ravine, but are saved by Naruto. Yamato and Sai ask Disonasu for information, prompting him to show them a book revealing the origin of The Hole; a great power resided within many years ago and nearly consumed the world. In his sleep, Naruto sees himself in front of the Nine-Tails' cage within his subconscious as he is surrounded by the snakes he had previously ingested. Naruto and Dokku discuss Dokku's failure to save a girl in his prime and all his failures in life, unlike Naruto, who became famous even in the Hachō Village, a rural area. Kabuto, while testing the effects of his talismans on Hidan and Deidara in a graveyard, converses with an unknown individual that communicates to him through a scroll.

After having what was seemingly a bad dream, Miina runs to Dokku in the night to seek comfort. Elsewhere, in a graveyard, Kabuto Yakushi prepares to reincarnate ] another individual. When day breaks the next morning, Leo, Faz and Lando are eager to start their ninjutsu training with Naruto, who is feeling under the weather. However, after being chided by the boys since he had made a promise to them, Naruto emphatically begins the training, which even Shiseru decides to partake it, having found it interesting. While elsewhere a reincarnated Deidara and Hidan's genetic clone argue over their predicament, having killed several members of the Hachō Village militia, and are later confronted by several more members along with Yamato and Sai. Plagued by vivid images all day, Miina approaches Naruto and begins repeatedly saying "get out". Thinking that Miina was simply being rude, Shiseru punishes her and Miina runs off. Later, Disonasu visits their home and, to everyone's surprise, the Tonika Village Head is with him. Greeting his grandchildren, he notes that he had injured his eyes but presses on past that, asking Dokku for the piece of the treasure he had given to him the night of the invasion of the village. However, Miina alerts everyone to the fact that there was something strange about her grandfather and it is revealed that he had been reincarnated. As a fight subsequently breaks out when Kabuto makes an appearance, Naruto soon begins writhing in pain. Rushing towards him, Miina once again begins shouting "get out", eventually forcing the tiny snakes out of his body. The snakes then form into a clone of Naruto in his four-tailed Version 2 state, which attacks all present individuals, including Kabuto, who is unable to gain control of it through a talisman. As the creature continues attacking indiscriminately, everyone looks on in fear.

The Nine-Tailed Naruto clone tries to attack Dokku and the orphans, when [Gai (Might Guy) and Rock Lee arrive to repel it. While they fight the beast, Kabuto tries to control it, but to no avail. The rest of Konoha 11 arrive,Team Asuma's help. Sakura and Kakashi and Team Kurenai help Naruto. Tenten and Neji arrive, but are cornered by the reincarnated puppets. Kakashi chases Kabuto. The beast grabs Naruto to absorb chakra, which the Nine-Tails gladly shares. Hinata tries to defend Naruto, but is sent flying. After the beast absorbs Naruto's chakra, it grows in size and starts to devastate the Hachō Village, even firing a Tailed Beast Ball in far away, missing Yamato, Sai, Deidara and Hidan who are fighting outside the village. Dokku tries to save Naruto, who is still unconscious. Moments before the beast tramples them, Kabuto summons a snake to swallow both of them alive and retreats. While inside the underground hall in the Tonika Village, Naruto, unconscious and strangled by snakes, meets the Nine-Tails again in his subconscious.

The Konoha-nin investigates Kabuto's intention in the meanwhile. Shiseru remembers an earlier conversation between her and Dokku about the pros and cons of them adopting the kids. While the Nine-Tails tries to control Naruto, Dokku calls him, but gets shouted instead. Dokku asks Naruto what burden a powerful person carries and made Naruto choose the reason why he desires to be powerful, seeing flashbacks of his comrades of Konoha and Sasuke, leading to the seal inside Naruto to gain strength again. Dokku gives Naruto his forehead protector, stating that he believes in him. Meanwhile, Leo decides to save their teacher by giving the mysterious iron bars which were mentioned earlier by the Tonika Village Head. While inside the hall, Kabuto, along with two reincarnated puppets, approaches with Disonasu, revealed to have engineered Tonika's destruction. Disonasu pulls out a scroll from which emerges the item that he desired: the Saezuri.

While the Saezuri is revealed, learning that Disonasu employed Kabuto Yakushi to wipe out the residents of Tonika Village, Dokku tried to attack Disonasu, but stopped by a reincarnated puppet and restrained by a resurrected Takigakure shinobi. Disonasu also praised Naruto about defeating Pain, the one who scarred him and left him powerless, before kicking the boy repeatedly. Miina and the orphans came to The Hole to give the iron bars, but Kabuto's clone intercepted them. Meanwhile, the rest of Konoha 11, along with Kakashi, Shiseru, Yamato and Sai moved out to the area. Disonasu prepares the summoning of the "power" by putting the remaining iron bars while Naruto enters Sage Mode. Miina hums to the sound as the Saezuri is activated, causing the area Naruto is on, the Ama no Hoko, to rise above ground. Kakashi arrived on the scene, revealing Disonasu's past as a bloodthirsty murderer and former Akatsuki subordinate whose specialty is the field of Summoning Technique, having researched Impure World Reincarnatio with Orochimaru. Kabuto summons his puppets, the Nine-Tailed Naruto Clone, Hidan, and Deidara. Naruto faces off with the clone, while Deidara uses Explosive Clay to create a diversion and chase Naruto.

Disonasu escapes and Hidan faces Shikamaru. Deidara activates the Explosive Clay on the bodies of the resurrected individuals, as Hidan uses his ritual against Team Asuma, and Sakura got restrained by Hayate and the others. While Naruto relentlessly attacked the clone, he learned there is more than power. As Yamato restrained Disonasu, he activated the Saezuri, opening the area where Naruto faces the clone, draining the lake as an obelisk rises and creates a storm. After Hidan's clone body breaks down due to the shorten life spans of the snakes composing his body, Deidara is controlled by Kabuto to escape Kakashi. A lightning hit the area where the orphans are running, Miina pointing to the obelisk. When the storm expands towards Konoha, Tsunade goes out as the storm engulfs the Land of Fire. Naruto tried to stop Disonasu from ascending the tower, only to face his clone after he absorbed some of the tower's power and transformed a Hydra-tailed fox monster.

Absorbing the power within the Ama no Hoko, the Nine-Tailed Naruto Clone mutated into a hydra-tailed version of the Nine-Tails while sending Disonasu to his death. Overpowered, Naruto almost gave in to the Nine-Tails' offer for power when Minato's voice urges the boy to control the tailed beast as Naruto is engulfed in a six-tailed chakra cloak in the Nine-Tails' image. Over time, as he starts to lose against the clone, the Nine-Tails starts to take control over Naruto's body and assumes a seven-tailed jinchūriki state with Yamato trying to restrain it. At the same time, though followed by Kakashi, Kabuto Yakushi manages to take his leave in midst of the ensuing chaos. Dokku and Shiseru decide to deactivate the Ama no Hoko and say good-bye to the children. On their way there, they confess their love for each other and decide to get married if they survive before portions of the ground start to sink, with Dokku keeping Shiseru from falling.

By that time, Miina is able to get through Naruto, regaining control as he assumed a new form to save Shiseru after telling Dokku to go forward and stop the Ama no Hoko. As Dokku recalls the tune Miina hummed to change the sounds in the Saezuri to deactivate the tower, Naruto uses his new power to destroy his clone as the Ama no Hoko recedes into the ground. Everyone, including the Konoha 11 and children celebrate with Naruto.

Adventures at Sea arc
Given the day off, Sai spends it strolling the village and drawing. He initially encounters three children that he at first finds it difficult to interact with, but later he realises that two of them remind him of the times he had spent with Naruto and Sakura. He has several flashbacks of their time together and the bonds they share. In the end he uses the doors of a destroyed house and paints a mural of Team 7 along with Sasuke holding hands.

Fourth Shinobi War arc
When the Fourth Shinobi War began, Sai was placed in the Surprise Attack Division. He created birds with his Super Beast Imitating Drawing for his Division to head into battle. When they entered the enemy's territory and the rest of the division began making a base camp, Sai took to the air to provide back up in case they were attacked. When he later spotted several explosions near the camp, Sai rushed back, eliminating one enemy as he arrived. Despite having a broken neck, the target got back up, revealing himself to be a reincarnated Shin. Shin apologised to his brother for being forced to fight him, unable to control his own movements because of the technique he was reincarnated with and because he was also being manipulated by Sasori. Sai and Shin traded blows until the rest of ambush team could come to help. Hoheto Hyūga revealed that there was explosive clay stored within Shin. They navigated him into one of Kankurō's puppets before he could detonate, weakening the explosion.

However, the force was still great enough to knock Sai over, causing some of the belongings from his bag to fall out. Shin regenerated from the damage and Deidara promised to use Shin as a human bomb again and again. Enraged, Sai quickly navigated behind Deidara and Sasori and drew two ink warriors that knocked them both into two more of Kankurō's puppets, where they were confined and neutralised. Sai then prepared to fight Shin again, but Shin told him there was no need; Sai had dropped his picture book earlier, and seeing the finished product had unbound his soul, freeing him of the regrets that he had had in life. Tears flowed from Sai's eyes as Shin's body turns to ash and dust.

Sai, Omoi, and Zaji were sent out to find other Akatsuki cells. When they came across a group consisting of Haku, Zabuza, Gari, and Pakura, Sai created several ink birds with explosive tags attached to bombard them with. Although the revived ninja recovered from their injuries, Sai continued the assault until backup could arrive. Haku managed to destroy the birds they were riding on, causing them to fall to the ground. Before they could be killed, fortunately, the Third Division arrived to help. They later joined the division in protecting Kakashi as he executed his strategy.

After Zabuza and Haku had been dealt with, Kakashi asked that Sai back him up with the sealing techniques he had learned from Root. Sai was reluctant, but Kakashi insisted that, as one of Danzō's most prized soldiers, Sai needn't hold his emotions. Later, Sai was seen among the rest of the Third Division as they recuperated after the first day of war.

The next morning, Sai alongside the Third Division restarted their assault on the Seven Ninja Swordsmen of the Mist. Drawing a gigantic tiger, Sai launched his Sealing Technique: Tiger Vision Staring Bullet at Fuguki Suikazan who had been incapacitated by Kakashi. As the tiger dragged Fuguki back into the drawing, a noticeably winded Sai told them that he could still go on. Lee told Sai to just concentrate on sealing the enemies, he would protect him while Sai's at it. As a new wave of White Zetsu Army clones approached, Sai looked on as Naruto's shadow clone arrived on the battlefield to confront them. In the anime, Sai also used this technique to seal away Jinin Akebino, and a number of other reincarnated shinobi as well. After being informed by Inoichi from HQ that Naruto and B were fighting the "masked Madara", Sai and the Konoha 11 rushed to his aid.

As he ran, he stated that if it were not raining, he could use his Super Beast Imitating Drawing technique to get to Naruto faster. After Lee had, however, spurred him on, Sai thought to himself that he finally and completely understood what it meant to have friends.

Upon arriving at the battlefield, he apologised to Kakashi for their late arrival and later stood alongside the remaining members of the Allied Shinobi Forces to face their opposition. When B had regained enough chakra, Sai flew him towards the Ten-Tails atop one of his birds, allowing B to get close enough to launch a counter measure against the beast.

Later as the Ten-Tails matured and the Alliance launched a counter assault, Sai attempted to attack the Ten-Tails' body from above, avoiding its copies, but was soon spotted and knocked out of the sky. After being saved by Naruto, Sai concluded the only way to reach the beast was to take out the larger enemies first and slither past, but that would require a method to get into range quickly and once they were there they would be without healers. His team-mates of Team Kakashi responded by summoning a snake, a toad, and a slug respectively.

While the Allied Shinobi Forces and the deceased Hokage marvelled at the original Team 7's combined performance, Sai questioned Jūgo about Sasuke's true motives, to which he replied that even he himself didn't know. He would later tell Sakura that since he didn't know Sasuke much he could observe him without friendly feelings involved and that he couldn't trust him. He proceeded to question Sakura how she truly felt about Sasuke, to which she replied that she was happy Sasuke had returned and that they could trust him. Sai then thought that sincere as her words sounded, her smile was fake.

After the Ten-Tails transforms into its true, tree-like form, it ravaged the Alliance in an attempt to consume their chakra. Sai, seemingly having avoided the assault, crouched and tended to a wounded Sakura. Thankful that Sakura was all right, their attention is soon drawn to Shikamaru's predicament. When Katsuyu noted that it would not be able to remotely assist him because its clones had been killed as well, Sai and Sakura rushed to Shikamaru's side to help their fallen comrade. Responding when Naruto called for them telepathically, Sai the Konoha 11 shinobi are shocked when Naruto's Tailed Beast Mode mantle forms around them as well when he enters one of Kurama's tails. His directives clear, Sai and the others used the Rasengan, which Naruto had formed to break down Obito's defence and give Sasuke and Naruto a clear shot at attacking their opponent.

He and his comrades later also aided Naruto in wresting control of the tailed beasts' chakra from Obito in order to stop the Shinju from blooming. Ultimately, they succeed in removing the tailed beasts from Obito, reverting the Uchiha to his original form. Sai then joins the others in aiding Hashirama against Madara.

After Hashirama is able to subdue the Uchiha, Sai moves in to seal him for good. Moments before the seal is complete, Madara has Black Zetsu merge with Obito, forcing him to revive Madara, granting Madara full access to his newfound might and break free of both Sai's seal and Hashirama's restraints.

While much stronger than before, Madara was now deprived of his dōjutsu powers and even sight, having removed his eyes years before his death. Sai then team up with Sasuke, letting the reformed Uchiha perform a sneak attack from the air.

Naruto Shippuuden movie 2
Sai, due to his ability to create flying mounts for himself with his Super Beast Imitating Drawing Technique, served a double function as a scout and first counterstrike against the Land of the Sky attackers by using taijutsu to jump and wreck different the Land of the Sky shinobi wing sets. He admits, soon after, that he is actually bored with the incompetence of the Sky ninja.

Naruto Shippuuden movie 3
Although not officially given a mission, after recovering from previous injuries, Sai pursued the Konoha 11 on their way to Hiruko's base. Temporarily blinding San with a flashbomb, he picked up Naruto and Sakura in order to get them ahead of the following teams, leaving Shikamaru and his team-mates to deal with San.

Naruto Shippuuden movie 4
When Naruto and Yamato are taken into the seal Mukade broke, Sai saves Sakura from being pulled into it as well. When Naruto and Yamato reappear, they all go back to Konoha.

Naruto Shippuuden movie 5
Sai appears along with the other members of the Konoha 11, Kakashi, Yamato, Guy, Shizune, and Tsunade to help save Naruto from the Hōzukijō and help defeat Satori.

Naruto Shippuuden movie 6
The alternate world's Sai, compared to the Sai that Naruto and Sakura know, has more emotions within himself and is more outgoing. His passion for art is the same, the only difference is that his alternate self is horrible at it. Also, due to the alternate Sasuke still being part of Team 7, the alternate Sai never became a member of Team 7 nor does he know the others.

Video Games
Sai is a playable character in the following video games:
 * Jump Ultimate Stars
 * Naruto Shippuuden: Clash of Ninja Revolution 3
 * Naruto Shippuuden: Gekitō Ninja Taisen! EX 2
 * Naruto Shippuuden: Gekitō Ninja Taisen! EX 3
 * Naruto Shippuuden: Gekitō Ninja Taisen! Special
 * Naruto Shippuuden: Kizuna Drive
 * Naruto Shippuuden: Legends: Akatsuki Rising
 * Naruto Shippuuden: Naruto vs Sasuke
 * Naruto Shippuuden: Ninja Destiny 2
 * Naruto Shippuuden: Ninja Destiny 3
 * Naruto Shippuuden: Shinobi Rumble
 * Naruto Shippuuden: Ultimate Ninja 5
 * Naruto Shippuuden: Ultimate Ninja Heroes 3
 * Naruto Shippuuden: Ultimate Ninja Storm 2
 * Naruto Shippuuden: Ultimate Ninja Storm 3
 * Naruto Shippuuden: Ultimate Ninja Storm Generations
 * Naruto Shippuuden: Ultimate Ninja Storm Revolution

Quotes

 * (To Uzumaki Naruto) "The way you fight, are you a boy or a girl?"
 * (To Sakura) "A smile can get you out of a tough situation, even if it is fake."
 * (To Haruno Sakura) "I've drawn hundreds, maybe thousands of pictures so far… other pictures have the situation at the time, and the artist's feelings… like portraits have the person's name… but don't pictures usually have titles…? To be more precise, even if I try to give them titles, I just can't do it. I don't feel anything… they don't put me in mind of anything."
 * (To Sakura) "…I don't have any of what you'd call "emotions"."
 * (To Uchiha Sasuke) "Even when I force myself to smile. It seems I'm the type of person who ends up being hated."
 * (About Sasuke) "…yet by just looking into his eyes, does this mean I fear Sasuke deep within my heart, despite being unable to recognise it myself…?"
 * (To his team) "Sai is the name I was given for this mission… I'm nobody. I am a tool for Lord Danzo. I don't exist."
 * (To his team about his adoptive brother) "We weren't connected by blood, but he did compliment me on my drawings quite a bit."
 * (To his team about the picture book) "The centre of two pages were the ones I wanted to show my brother the most, but since he's dead, I can't remember what I wanted to draw on them."
 * (To Kabuto) "If people change… then so can I. But some things never change. Bonds. I'd like to learn more about them."
 * (After finishing the picture book) "This is what I wanted to show my brother. The picture of our dreams."
 * (To Sakura) "Lately when I look at Naruto I've been able to feel it… his sadness. And when he thinks of Sasuke there's a heat coming from his gut and I know that's anger. For Naruto's sake, for Konoha's sake, we need to do something ourselves instead of always relying on him."
 * (To himself) "This… is what it means to have friends… I understand it perfectly… Naruto."

Knownable Relatives

 * Shin (Adopted Older Brother/dead)
 * Uzumaki Naruto (Best Friend/Teammate)
 * Haruno Sakura (Friend/Teammate)
 * Uchiha Sasuke (Friend/Teammate)
 * Hatake Kakashi (Sensei/Friend)

Trivia
According to the databook(s):
 * As an ANBU member, Sai refers to Kakashi as his Senpai out of respect.
 * Sai's hobbies are drawing and calligraphy.
 * Sai wishes to fight Hatake Kakashi.
 * Sai's favourite word is '"Comrades" (仲間, Nakama).
 * Sai's favourite food is momen tofu, while his least favourite is mitarashi dango.
 * Sai has a frank, obedient and submissive personality.
 * In the seventh Naruto Shippuuden opening, Sai is shown fighting Asura Path, though in the manga, they do not fight; in fact, he isn't even present in Konoha when Nagato and Konan attacked.
 * In the seventh character poll, Sai placed 12th place, alongside Sakura, with 2,188 votes each.

Voice Actors
all information on Sai came from http://naruto.wikia.com/wiki/Sai
 * Japanese : Satoshi Hino
 * English : Benjamin Diskin