Yamanaka Sai

Yamanaka Sai (山中サイ) is a Chubu level Anbu of Konohagakure's Yamanaka clan. Prior to this, he was a regular Anbu from Danzo's Root group. As per standard Root training, Sai was conditioned to remove all emotions and as such, has difficulty connecting with others. After he is put on Team Kakashi as a replacement for the rogue shinobi Uchiha Sasuke. Sai begins to learn more about people's feelings, and tries to develop his personality and identity. Thus he learns to form genuine bonds, and rediscovering the emotions he was taught to suppress.

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 his Surrogate 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 Danzo but Shin died before the battle could be finished. Shin told Sai to report to Danzo 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. In an attempt to gain a powerful fuinjutsu after seeing Sarutobi Hiruzen sacrifice his life in an attempt to defeat Orochimaru, Danzo 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 tends to get people angry, because he often speaks 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. Sai nearly called him "fatso", however Naruto covered his mouth before he could finish. While realizing he was offending people by saying characteristics that came to his head, Sai decided to take a different approach by saying the opposite of what came into his head. In this way, at the same time Sai called Ino "gorgeous" (although he truly meant to call her "ugly"). This caused Ino to be very surprise, along with Naruto to be relieved, however Sakura was angry.

After spending more time with Team Kakashi, Sai comes to appreciate bonds, a specialty the bond between Uzumaki Naruto and Uchiha Sasuke. However Sai would come to have his doubts about Sasuke when he began to commit crimes on an international scale, which Naruto would suffer for. This causes him to break out of his emotionless shell and start 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. In the anime, it was shown from his Infinite Tsukuyomi dream that his greatest desire is to fully rediscover his emotions and connect with as many people as possible through it.

He later appeared to show genuine anger while explaining to Sakura about Naruto's feelings for her and later when she lied to Naruto about the predicament with Sasuke and trying to use a fake confession to get him to give up on Sasuke. 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 became truly enraged for the first time and attacked Sasori and Deidara mercilessly, showing genuine rage on his face. Sai also displayed genuine sadness, shedding tears when his brother was 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 suffering without Naruto even telling him. What he failed to understand, however, was that Naruto was not trying to save Sasuke just for Sakura, something he mentions is due to his still lacklustre understanding of both his Team 7 teammates and emotions in general and he would come to regret when it lead to Sakura's suicidal attempt to stop Sasuke, feeling that as if he was a true friend, he should've found another way. Sai holds Naruto in high regard, and tries to assist Naruto whenever he's going through hardships however he can.

This bond with Naruto led Sai to start to understand camaraderie, and by the Fourth Shinobi War, he realised he understood it as he, Rock Lee, and various others went to assist Naruto as he fought against Tobi. Growing up over the following the years, Sai came to truly understand compassion and love, forming a closer bond with Ino, showing more forwardness in such acts as asking her on a date and holding her hand affectionately. This ultimately led to them forming a family. Through all this, Sai has completely come to reject the teachings of Root, accepting that Danzō's intension, while genuine to protect the village, were misguided and only led to more suffering.

Sai is shown to care greatly for his family, as he has begun training his son in his artistic-ninjutsu, finding humour in Inojin's cruder drawing. Sai also has developed strong parenting skills, being the one who's reprimanding Naruto for not holding back enough when he tried to counter Boruto's shadow clone with his own. His compassion for his son's happiness was also shown from not wanting to hurt any of his friends, regardless of the circumstances. He also believes in a indirect teaching-method, feeling that while people need guidance, they cannot truly grow as people if they don't find the answers themselves.

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.

Two years after the Fourth Shinobi War, Sai's hair grew longer with his bangs framing his face. His attire is similar but both sleeves of his shirt are long and his boots reach more above his calves. He also has a large scroll strapped horizontally to his back.

Many years after the Fourth Shinobi War, Sai's jacket now is long enough to cover his entire upper body, with both sleeves long. He continues wearing a scroll on his back and long sandals, but his pants are slightly different.

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.

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. Even without the use of his tante, he has shown great skill with a bladed weapon and was able to fight equally with an opponent wielding a larger weapon. A distinct advantage he has in battle is to perform techniques with a single hand, leaving the other free for enemy counter-attacks.

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

Fuinjutsu
As noted by Kakashi, Sai is one of Danzo's prized soldiers and as such, his Root training also included learning fūinjutsu. With the Sealing Technique: Tiger Vision Staring Bullet, he can trap people within his paintings by using a giant brush and drawing a tiger on a large scroll. Due to the preparation time it would take, he would need 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.

Nature Transformation
Sai is able to use Earth Release to conceal himself underground without disrupting the surface of the earth. He can also use Fire, Water, and Yang Release.

Sasuke & Sai arc
Sai was assigned to join Team Kakashi by his superior Danzo to assist in meeting with a spy in Orochimaru's ranks to find out about Uchiha Sasuke. Sai was confrontational with his new team-mates upon their first meeting, exasperated both Uzumaki Naruto and Haruno Sakura. 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 Danzo had ordered Sasuke be killed as a traitor. Sai was surprised since Danzo 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 apologized 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. Hyuga Hoheto 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, Momochi 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 Hatake 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 Danzo'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 Uzumaki 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 Rock 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 apologized 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 dead Hokage marvelled at the original Team 7's combined performance, Sai questioned Jugo about Uchiha Sasuke's true motives, to which he replied that even he himself didn't know. He would later tell Haruno 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. 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 Nara 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 Uchiha 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 Senju 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.

After being revived and gaining access to his full power, though without his dojutsu, Madara was easily able to overwhelm the shinobi in the surrounding area, including Sai, before absorbing Hashirama's senjutsu chakra and going to capture the nine Tailed Beasts. Sai then teamed up with Sasuke, letting the Uchiha perform a sneak attack from the air through the use of a ink bird.

Much later, after Madara became the Ten-Tails' jinchuriki and reclaimed his missing eye, Sai stood next to Hashirama while the Infinite Tsukuyomi was cast, before falling prey to it like the rest of the world and being captured by the roots of the Ten-Tails. In the anime, Sai dreams of learning to properly express himself again and the village came to admire his smile.
 * Tsunade's Infinite Tsukuyomi dream

While being informed by Danzo that Sasuke is to become Orchimaru's next vessel, Sai is sent with Hayate, Yugao and Anko to stop Naruto and Shikamaru, even if it means killing them. She and her group sneak out of the village, while unknown to them that Neji spotted them. Once Sai and his group catch up to Naruto and Shikamaru by sending flying Kunai's at them, Naruto tries talking the group out of attacking them, but the group don't listen. Sai stays back to watch the fight from the sidelines. So he watches Anko go into battle with Naruto, while Shikamaru battles Yugao. But Neji, Rock Lee and Tenten arrived just in time to help Naruto and Shikamaru fight the ANBU. He and his group fall back except for Anko and Naruto, who are still fighting. Once the sunlight shows up, Sai and his group are reveal to Shikamaru, Neji, Rock Lee and Tenten. Upon realizing that the ANBU are trying to kill them, Shikamaru realizes they don't serve under Minato because they would never kill Naruto and Neji says he heard about a separate ANBU faction secretly led by someone else that trains them. This leads to Neji and Shikamaru learning that this secondary ANBU is known as Root.

Naruto finally manages to unmask the Root member fighting him, revealing her to be Anko. Anko then manages to cut Naruto's right cheek and licks the blood off his cheek with her tongue, which scares him like crazy. Shikamaru realizes their mission, and has the group flee from the fight and continue pursuing Sasuke. While running away from the ANBU, Lee stays behind to stall all the Root shinobi, but Hayate engages him, allowing the others to continue. Once the ANBU gets closer to them, Tenten stays behind to fight Yugao. Thus Naruto, Neji, and Shikamaru continue to give chase, while being followed by Anko and Sai.

While finally reaching the tower that Sasuke is at, Neji decides to fight Anko and Sai while Naruto and Shikamaru run to go into the tower. As Neji begins his fight with Anko at the bridge, she reveals that this Sai that is with her is an Ink clone. Sai finally revealed himself using his big ink bird in the sky while trying to stop Naruto and Shikamaru from reaching the tower. While in the air he throws flying shurikens at Naruto and Shikamaru as they reach the inside of the tower. Shikamaru decides to handle Sai by himself outside while Naruto goes inside the tower to get to Sasuke. As Sai and Shikamaru's fight begin, Shikamaru destroyed Sai's ink bird making him land on the ground to fight him. When Shikamaru catches Sai with his shadow technique, he also tells Shikamaru that he has no grudges against this is his mission. Then Sai tells that the weather looks nice tonight, which Shikamaru notice that his shadow had disappeared. Sai reveals that his shadow technique is useless because they are in the dark, they then continue their fight off screen. Sai then retreats from the battle to meet up with Anko, Hayate and Yugao in order to make sure that Sasuke is with Orochimaru.

Ultimately, Sai was freed from the genjutsu by Naruto and Sasuke as the war finally ended. Later on he attended Neji's funeral.

Blank Period
Nearly a year after the end of the Fourth Shinobi War, Sai and Naruto are on a mission in the Land of Waves to capture Garyō, leader of the Ryūha Armament Alliance, a group that follow the example set by Uchiha Madara, and in doing so has cost the lives of several of the Land of Waves' citizens. While dealing easily with most of the enemy forces, Garyo's bodyguard holds them off using Ice Release. Garyo insists that his group is doing the world some good by releasing it from the corruptive influence of money. Ultimately, Sai and Naruto capture Garyo on and leave on Sai's bird.

Two months later, when the Tobishachimaru, an airborne ship, is commandeered by Garyō's men in an attempt to free him from the Hozuki Castle, Sai is sent to aid Kakashi in the air. Sai arrives in to save Kakashi and Guy as they begin falling from the sky. Kakashi informs Sai of what they learned about the Armament Alliance's shinobi and asks how things are going on Konoha's end. Kakashi sends a message to Ino that Tobishachimaru is heading to Blood Prison and asks Sai to take him back to the ship so he can try and stop it. Sai complies, but finds the Tobishachimaru has risen well above its usual altitude owing to the ongoing conflict on board. After getting Kakashi back inside, the hijackers agree to let Sai take a young boy with asthma off the ship but is warned they will kill a hostage if they see him again.

Two years after the war ended, one of Sai's ink birds approaching the office of Kakashi Hatake, the Hokage. Eager to finally have news about Sai's mission, Shikamaru rushes to the Hokage to hear his report. During the War and every month since then, a large number of shinobi (almost exclusively young, single men) have been deserting their hidden villages and then disappearing. The number of missions has also seen an unusually sharp decline. From investigating both matters, Kakashi believed the Land of Silence - a samurai-run country on a distant continent - was involved. He sent Sai and a team of ten Anbu to investigate.

Kakashi and Shikamaru are concerned by a number of things in Sai's message: the clear haste it was written with, not having Sai's characteristically clear handwriting; his report that his entire team has gone missing; his warning of the threat posed by Gengo, the Land of Silence's strangely charismatic leader; Sai's choice of words that suggest he is awed by Gengo and doubtful of the Shinobi Union. What troubles them most, however, is the fact that Sai did not deliver the report in person. It is apparent to Kakashi that, if nothing is done, the Union will inevitably go to war with the Land of Silence. In order to avoid this, Gengo must be assassinated. Shikamaru does not hesitate to volunteer for the job, chiefly so that he can try to find Sai.

When Shikamaru rushes at Gengo in order to perform the assassination himself, but is intercepted by Sai, now an Enlightened One. Sai attacks him with numerous ink tigers and Shikamaru tries to counter with his Shadow Sewing Technique, but Gengo commands his shadow to stop. Shikamaru is captured and imprisoned, forced to listen to the tortures of Rō and Soku while he must only endure occasional smalltalk from Gengo.

When Shikamaru tries to go after Gengo, Sai attempts to stop Shikamaru but his way is blocked by Temari, who has been desperately searching for Shikamaru ever since he left for the Land of Silence. She summons Kamatari to destroy Sai's ink animals, but he pierces through her giant folding fan to stab her with a kunai. He moves in for a finishing blow with tears in his eyes, but he's restrained by Choji. Sakura heals Temari's wound and Ino delves into Sai's mind in order to break Gengo's hold over him. She finds him trapped deep in his consciousness, wrapping himself with memories of his friends. She helps him break out and he thanks her with a heartfelt smile.

After Gengo's arrest, Shikamaru checks on Sai and assures him that he is not to blame for anything he did while under Gengo's control. Just as he leaves Sai's side, however, Shikamaru is immediately assaulted by Naruto, who is upset that Shikamaru would put himself in danger without telling him. Shikamaru promises to never keep anything from Naruto ever again. Most of the Konoha and Suna forces return to their villages, but with a small force Naruto and the others remain behind to help the Land of Silence return to normalcy after Gengo's arrest.

Later, as Naruto began dating Hinata, he borrowed one of Sai's instruction books about relationships, particularly about dating protocol. A week later, Kakashi meets with Sai and tells him about two separate attacks by unknown perpetrators against the Fire daimyo and Mitokado Homura. Although nobody was badly hurt and there's no proof the two attacks are connected, Kakashi wants Sai to investigate both incidents by himself. Sai meets with an informant just outside of Konoha and sends him to investigate if some criminals listed in the Bingo Book are behind the two attacks. As he returns to the village, Sai is attacked by two masked individuals. Although each of the attackers has a cloak of tailed beast chakra, he is able to drive one of them off and capture the other. Sai starts questioning the captive, but when the man begins to respond a juinjutsu activates and his body blows up.

When Kakashi returns to his office he is met by Sai, who tells him of the earlier attack he fought off. Both observe that the attacker's suicidal juinjutsu is similar to what Danzo used on his agents. This, combined with the fact that nobody but an Anbu could have even guessed Sai's assignment and thus known to attack him, convinces Kakashi that it is all part of a scheme concocted by Kido Tsumiki, a former ally to Danzo. Kakashi instructs Sai to focus his investigation on Kido.

Sai follows Kido's movements between his different hideouts for three days, but he has no way of getting inside any of them without revealing his presence. His informant requests a meeting and, there, reports a rumour about Sasuke: that he approached some arms dealers several weeks earlier seeking weapons for an attack on Konoha, and then killed the dealers when they failed to cooperate. He also reveals that, after the war, he saw an Anbu collecting samples from the Valley of the End and the bridge where Sasuke fought Danzo. Sai pays him for this information and requests another meeting in the future.

Sai runs into Sakura afterwards and she tells him her theory, which makes enough sense to him that he asks her to accompany him to Kakashi's office. 1.With Sakura's theory and his informant's earlier report about Anbu activity at the Valley of the End, Sai believes the Anbu – specifically Kido and Magire – are behind the Sasuke impostor. He also believes this would explain the tailed beast cloaks he encountered, with those being drawn from skin and hair samples taken from Naruto and other jinchūriki. Since Sakura, Sai, and Ino are apparently all investigating the same thing, Kakashi makes them a team; Ino dubs themselves "Ino-Saku-Sai" (猪サクサイ). The three agree to continue their investigations and keep each other informed of their findings.

Later while taking a shower at his house, he hears someone knocking on his door. He then answers the door, and learns that it is Ino who needs his help. She tells him that Sakura is missing and they assume she's been kidnapped by Kido. While he gets dressed, Ino contacts Kakashi and informs him of what's happened. He advises not getting anyone else involved in the rescue as that might only provoke Kido to kill Sakura. He also informs them that the Fourth Raikage is contemplating a Kage Summit to discuss reports of Sasuke's activity.

Sai and Ino go to one of Kido's hideouts and Ino senses the interior for Sakura's chakra. Sakura isn't there, but Sai decides they should see what intel they can get anyway. Ino uses the Mind Body Switch Technique on the hideout's sentry while Sai captures them, her first time using such a tactic without Shikamaru or Chōji. When the sentry, an acquaintance of Sai's, is unwilling to answer their questions, Sai forces Sakura's whereabouts from him by tickling him with a paintbrush. They go to the hideout where Sakura is being kept, but find that she's already escaped and is on the offensive.

She and Sai finally found Sakura, which leads for them to work together. Sakura, Sai, and Ino work well together despite being outnumbered. Sakura is drawn into a fight with the Sasuke impostor, who chokes her using his synthetic tailed beast cloak. Sakura breaks free and, as she beats him unconscious, warns him to never impersonate Sasuske again. This has the added benefit of revealing that the synthetic cloaks disappear when their user loses consciousness; Sai and Ino also discover that the cloaks have time limits. Sai recommends they use this information to end the fight quickly.

Sakura, Sai, and Ino defeat all but Kido and Magire. Because Magire is a medic-nin, they decide to separate Kido from him so that Magire can't heal his injuries. Sakura leads Kido away into a nearby forest to fight him by herself. When she repeatedly dodges his lightning jutsu, Kido activates a synthetic tailed beast cloak.

Sai and Ino exchange attacks with Magire, but neither side is able to hit the other. Magire activates a synthetic tailed beast cloak and, with its tails, is able to create glowing orbs that detonate on contact. While Sai tries and fails to overpower Magire with his Super Beast Imitating Drawings, Ino takes control of a passing eagle which she uses to stab Magire from behind with a poisoned kunai. Magire's movements become slow, allowing Sai to deliver a finishing blow. Kakashi arrives to help as soon as Magire is defeated, with Naruto and Hinata tagging along. Together they head into the forest to help Sakura.

As Sakura is verifying that Kido has been defeated, she is joined by Ino, Sai, Kakashi, Naruto, and Hinata. They congratulate her on her victory, but are interrupted by news that several of Kido's Anbu have fled the village. Though he can't move, Kido explains that they're going to continue his plans. Sakura and the others immediately give chase, but on reaching the Anbu they find them all defeated with a combination of fire and genjutsu. They guess that it was Sasuke's doing and that he chose not to stick around when he confirmed Kido was defeated. Although they're disappointed that Sasuke didn't at least say hello, they are glad that the entire ordeal is over. After Ino–Saku–Sai is dismissed by Kakashi, Sakura is called to a meeting with Suna-medics. Ino offers to go with her, but Sakura tells her to instead have lunch with Sai.

Many years later in Konoha, Kakashi assigns all the wedding's attendees a mission that is to be kept secret from Naruto and Hinata: bring a gift. Sai has painted something with so much passion that it flew away. In the anime, after doing a weird video message, Sai learns that everyone who gave Naruto a gift will have to do a mission on his wedding day. Therefore he and his friends tell Kakashi that they can do missions back and forth so this way they can still attend Naruto's wedding. On the day of the wedding, guests start arriving at the ceremony to be held under the Hokage Monument. Sai is seen happily holding hands with Ino. While everyone watches them.

A few months after Naruto and Hinata's wedding, upon learning from Kakashi that a genjutsu user was behind people disappearing, and wants Sasuke to assist due to his Sharingan and Rinnegan being able to cast out genjutsu. Naruto, Sakura and Sai are joined with Shikamaru, Choji, and Ino, on a mission to stop the intruders from putting people in a genjutsu. As they converse on what information they have on Tadaichi's disappearance and those in Kiri and Kumo. They find the Barrier Team ninja battling the intruders, and Ino recognizes one of them as Tadaichi. Sakura also recognizes the other intruders as the missing Konoha shinobi. Before they can engage in a fight, the intruders use an explosion to retreat and everyone suspects the missing shinobi were under a genjutsu. The missing shinobi explode due to the injuries received from Tadaichi's explosion. Yamashiro Aoba soon arrives to alert them that there are more intruders, revealed to be the missing Kiri and Kumo shinobi.

As Naruto and the others battle the intruders, Naruto's wife, Uzumaki Hinata, comes to their aid and uses her Byakugan to see if the opponents are under a genjutsu, which she says it is unlikely. They suspect that a different type of chakra is controlling the opponents and they can't injure them or else they will explode. Naruto uses Shadow Clones to distract the opponents while Shikamaru uses his Shadow Imitation Jutsu and Hinata used her Gentle Fist to hit their chakra points and render them motionless. Aoba uses his sensory abilities to enter a Kiri shinobi's mind but is caught in a genjutsu trap, and Ino uses her Mind Body Switch Technique to save him, both passing out. As Sakura cures Ino and Aoba, Sai takes everyone else to the hospital.

Epilogue

 * Boruto Naruto Next Generations (Anime)

13 years later, Sai eventually married Ino and took on the Yamanaka name. The two had a son named Yamanaka Inojin. In the anime, he would also work part-time at Yamanaka Flowers with his wife. Once Naruto became Hokage, Sai is seen speaking to his son and Shikadai. Later Sai along with Kiba, Choji, Rock Lee, Shikamaru and Shino help a unconscious Naruto arrive at his house. It turns out Sai and the others are also drunk.

When Inojin is in the Ninja Academy, as the mysterious attacks began happening more commonly and expanding in area, evidence was found to suggest that the real goal of the perpetrator was to harvest people's chakra. It was also discovered that Wood Release was possibly involved. As Root had a history of conducting its own secret research on the famed power of the First Hokage, Shikamaru decided to research if more with Sai. As the attacks continued to occur, Sai intensified his efforts. While Naruto told him to calm down, Sai was determined to save the potential culprit from following the misguided ideology of Root. Later, a strange release of chakra began spreading throughout the village. As it showed a similar nature to the chakra of the rampages, Sai went to act.

His investigation led to an old facility of Root, which turned out to be the hideout of the late-Tanuki Shigaraki, one of Danzo's top researchers and most loyal followers. Putting the pieces together, Sai remembered that Tanuki was in charge of creating an ultimate weapon made from the First Hokage's cells. While looking around the demolished building, he found a picture of Tanuki, with a young girl Sai immediately recognized as Sumire Kakei. After reporting his findings to Naruto, Sai and his unit went in search of Sumire, who disappeared from the hospital. Sai soon found her and subdued her. While preparing to take her in, she unleashed the Nue. The rampaging beast gave Sumire the chance to escape while Sai and his unit attempted to hold off the beast. Kakashi soon appeared, severing its tail, only for the creature to sprout dozens of smaller tails and steal people's chakra. As Kakashi organized the unit to hold off the creature, it suddenly teleported away.

Kakashi deduced that the creature acts differently from normal summonings, naturally existing in its own separate dimension. By morning, Sumire returned from the separate dimension along with Boruto and Mitsuki. Sai, still sympathising with Sumire's history with Root, offered to help her forge a new brighter path. Having let got of her anger at the village thanks to Boruto's words, Sumire accepted Sai's offer and peacefully turned herself in. Sai promised Boruto that she would be fine.

Later, Sai discussed the future of Sumire with Naruto and Shikamaru. Sai also removed Sumire's Ninja Academy records to weigh in their options.

On the day of the Five Kage Summit in Konoha, Ino becomes irritated that her son Inojin didn't turn up to his training, as Sai attempts to calm her down. The week before Inojin's Ninja Academy graduation exam, Sai practices his signature technique with his son. When Naruto and Boruto's sparing session interrupts them, Sai tells the Seventh it's petty of him to consider using multiple Shadow Clones against Boruto. Afterwards, Inojin tells him his taste in art is ancient.

The morning before training, Sai discovers that Inojin has been photocopying his Super Beast Imitating Drawing instead of drawing by hand due to finding it exhausting much to Sai's shock. However, during training Inojin loses the ability to perform the technique even after drawing by hand. After Inojin asks his father for the reason he can no longer perform the technique, Sai advises his son to enter a children's art competition much to Inojins displeasure. After Inojin loses to Himawari Uzumaki, Sai attempts to guide him by telling him to find the difference between him and Himawari. However, this only leads to Inojins frustrations building as he continues to fail in performing the technique which then causes him attempt to use his mothers Mind Body Switch Technique.

Whilst working together in their flower shop, Sai tells Ino of his belief that their son needs to find the solution to his problem on his own but Ino remains worried. Sai then comforts her by telling her that he has faith in Inojin because he is their son, causing Ino to become flustered.

Later, when a group of self-proclaimed noble thieves began making various heists throughout Konohagakure, their act of distributing their stolen wealth to the poor began gaining much support from many of the villagers. Even more, swarms of protestors began emerging in the village against various legitimate companies, fueled by the Byakuga Gang's claims of the said companies being corrupt, one of which included the Kaminarimon Company. In hopes of better understanding this new enemy, it was decided to talk to the other villages for any information on the Byakuya Gang.

Later, the villagers supporting the Byakuya Gang began acting out against companies accused of corrupt actions. Sai joined his fellow ninja in working to pacify the situation. Ultimately, it was discovered that several of the protestors were under genjutsu. Sai helped in dispelling the genjutsu. This along with Naruto's speech was able to peacefully end the riots.

As the next Chunin Exams drew nearer, Sai continued to watch over Sumire's development. He would regularly make contact with her jonin-sensei Hanabi, advising her to let Sumire go at her own pace for reconciling with her friends.

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.

Naruto Shippuuden movie 7
Two years after the Fourth Shinobi War, Sai was drawing a scenery outside of Konohagakure in the middle of the night, only to notice the moon's descent towards the Earth and a hooded shinobi riding on a flying creature while carrying the unconscious Hyuga Hanabi, much to his shock. He tried to chase after them, only to be taken down before he could rescue Hanabi. After reporting to the Sixth Hokage about Hanabi being kidnapped by Otsutsuki Toneri, he joins with Naruto, Sakura, Shikamaru, and Hinata on a mission to rescue her.

After Naruto is brought out of his depression by Sakura, she and Sai go to save Hanabi while Naruto and Shikamaru go after Hinata. After Toneri's defeat, the group heads back for Konoha. Later, Sai was seen at Naruto and Hinata's wedding. He was also seen holding Ino's hand, hinting they were in a relationship at the time.

Boruto movie
Sai is put in charge of the second phase of the Chunin Exams with Nara Shikamaru. He is lastly seen during the end credits. In the Boruto manga, after learning that Katasuke was being controlled by someone. Naruto has Ibiki and Sai continue investigating.

Boruto Naruto Next Generations Manga
In the anime, when two Chunin-level gate guards were attacked by unknown assailants, the village was put on lockdown. Sai oversaw the investigation of the attack, finding Mitsuki's forehead protector. Sai then reported to Naruto and joined him when overseeing Ino probe one of the guard's mind for answers, learning that Mitsuki had left willingly with the attackers. When Naruto revealed to the others Mitsuki was in fact Orochimaru's son, much outrage followed from learning that Naruto would permit an offspring of the man who killed the Third Hokage live in Konohagakure, let alone keep it a secret. Naruto rationalised this on the grounds that Orochimaru's conduct as changed from before and that his aid in investigating the Otsutsuki. Despite this, noting the unpredictable nature of Orochimaru, the meeting ended with deeming the Oto-born boy as a threat.

Sai then tells Naruto and Shikamaru that Yurito has explosive tags on him that are very dangerous. Because the explosive tags are C2.

Later, as talks about what to do about Mitsuki's apparent betrayal continued, it was reluctantly determined that they would have to place extreme punishment for Mitsuki. Overhearing this, Konohamaru insisted that he be the one to bring Mitsuki back, which Naruto reluctantly agreed to.

In the days following the Otsutsuki attack on the Chunin Exams, Sai and Ibiki report that Tono Katasuke was under mind-control to Naruto, and suggest it's likely that the perpetrator was after Konoha's technology. Afterwards, Naruto has them look further into the matter.

Later, after the Mujina Bandits were captured by Team Konohamaru, Sai and Ibiki were tasked with interrogating the leader, Shojoji. While arrogant at first and demanding compensation, the timely arrival of Sasuke and his dark reputation quickly swayed Sojoji to talk. While knowing very little, Shojoji explained that mark on Boruto's right palm was identical to one used by an organisation called "Kara". He also said that the marks' nature is vaguely similar to Orochimaru's Juinjutsu.

When Naruto decided to test Katasuke's new Scientific Ninja Weapon, Sai and Shikamaru watch Naruto test it against Boruto at the Training Hall. During the match, Sai comments how Boruto attacking his father from behind is a ballsy move.

Video Games
Sai is a playable character in the following video games:
 * Jump Forces
 * Jump Ultimate Stars
 * Naruto Shinobi Collection
 * Naruto Shinobi Collection Shippu Ranbu
 * Naruto Shippuuden Clash of Ninja Revolution 3
 * Naruto Shippuuden Gekito Ninja Taisen! EX 2
 * Naruto Shippuuden Gekito Ninja Taisen! EX 3
 * Naruto Shippuuden Gekito 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 Blazing
 * Naruto Shippuuden Ultimate Ninja Heroes 3
 * Naruto Shippuuden Ultimate Ninja Storm 2
 * Naruto Shippuuden Ultimate Ninja Storm 3
 * Naruto Shippuuden Ultimate Ninja Storm 4
 * Naruto Shippuuden Ultimate Ninja Storm Generations
 * Naruto Shippuuden Ultimate Ninja Storm Revolution
 * Naruto Shippuuden Ultimate Ninja Storm 4 Road to Boruto (non playable)
 * Naruto to Boruto Shinobi Striker
 * Naruto Ultimate Ninja Online
 * Naruto X Boruto Ninja Voltage

Uzumaki Naruto
When Uzumaki Naruto first met Sai, they had a rough start due to Sai's constant criticism and regards of Sasuke as a traitor. However, the two got to understand each other better during their attempt to retrieve Sasuke with Naruto now considering Sai a member of Team Kakashi. Inspire by Naruto, noting that Naruto reminded him of his own brother Shin, Sai works to become a more social person. Although his attempts can sometimes be awkward, and although Naruto's ties to Sasuke were his overall motivation for changing himself. Sai began to feel what he believed to anger over Sasuke becoming beyond redemption with all the grief that he caused for Naruto through his crime-riddled vendetta. During the Fourth Shinobi War, Sai finally reaches a full understanding of friendship before arriving to Naruto's side during his battle with the Ten-Tails.

Upon arriving at the battlefield, he apologized to Kakashi for their late arrival and later stood alongside the remaining members of the Allied Shinobi Forces to face their opposition. During the battle with the Ten Tails, Sai back up Naruto in his battle.

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 jump into action at the original Team 7's combined performance, Sai still couldn't decide to trust Sasuke or not.

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 defense 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 Ten-Tails' tree form from blooming. Ultimately, they succeed in removing the tailed beasts from Obito, reverting the Uchiha to his original form.

Much later, while the Infinite Tsukuyomi was cast, Sai fell prey to it like the rest of the world and being captured by the roots of the Ten-Tails. Ultimately, Sai was freed from the genjutsu by Naruto and Sasuke as the war finally ended.

Two years after the Fourth Shinobi War, Sai was about to draw a scenery outside of Konohagakure in the middle of the night, only to notice a hooded shinobi riding on a flying creature while carrying the unconscious Hanabi, much to his shock. He tried to chase after them, only to be taken down before he could rescue Hanabi. After reporting to the Sixth Hokage about Hanabi being kidnapped by Otsutsuki Toneri, he joins Naruto, Sakura, Shikamaru, and Hinata on a mission to rescue her.

After Naruto is brought out of his depression by Sakura, the team decide to go save Hinata and Hanabi. After Toneri's defeat, the group head back for Konoha. Sai also attended Naruto and Hinata's wedding. When Naruto finally became Hokage, Sai along with Choji, Shikamaru, Kiba, Lee and Shino help a unconscious Naruto arrive at his house. Sai and Naruto remained good friends over the next several years and both often comment on the other's parenting skills; Sai calling Naruto childish for being fooled by Boruto's shadow clone. While Naruto sees Sai calling himself immature when Inojin, calls his art old-fashioned.

Haruno Sakura
When Sai first met Haruno Sakura, she tried to hold back Naruto from attacking him due to the fact that Sai insulted him. Therefore she told him that name-calling was not nice. However Sai replied by saying he always likes people, and calls her "ugly". In response, Sakura tried to attack him. Sai made this even worse by condemning Sasuke as a traitor and Sakura angrily punched him, and threatened to hit him harder if he ever bad-mouthed about Sasuke again. While Sakura also admits that she doesn't care if Sai forgave her for hitting him.

However, as the two began to understand each other in their attempt to find Sasuke, Sakura began to consider Sai a comrade. This is more evident upon finding his art journal and deducing his desire to make friends. Sakura remained a bit wary about Sai when she learned he was ordered to kill Sasuke but accepted him more when his desire to help reunite Team Kakashi is genuine. When Sai noted Sakura and Naruto's friendship by their friendly name-calling, Sai wonders if he can give them nicknames as a friendly gesture, and Sakura says a nickname is based by a person's characteristic is. Sai then begins to call Sakura "ugly", which frequently angers her enough to hit him.

Although Sakura is the one who gives him ideas on how to make bonds with everyone, Sai comes to understand Sakura's feelings for Naruto and Sasuke. He ultimately comes to the conclusion that Sakura relying on Naruto to keep his promise on brining Sasuke back is causing him pain. When he confronts her about this, he also tells her that he clearly can tell that Naruto loved her. However, when Sai's words cause Sakura to decide to lie to Naruto about loving him, and secretly going to kill Sasuke to free him from hatred, Sai felt guilty for forcing this on Sakura and alerted Naruto out of concern for her welfare.

During the battle against the Ten-Tails and Sasuke's sudden arrival to help them, Sai told Sakura that Sasuke could not be trusted. Sakura, however smiled and said she was just happy he was back, but Sai could immediately tell that her smile was fake while her words were sincere. Two years after the war, Sai was assigned with Sakura, Naruto, Shikamaru, and Hinata to rescue Hanabi from Toneri on the moon. With Sai pairing up with Sakura to guard an unconscious Hanabi, while Naruto and Shikamaru go save Hinata from Toneri. After the battle was over, Sai along with Sakura and Shikamaru, took Hanabi out of the genjutsu lake. He and Sakura then saw Naruto and Hinata blasting through the lake to have their along time. He and Sakura remained good friends over the years. Even to the point that Sakura supported Sai's relationship with Ino. The two even went to Naruto's wedding by congratulating him.

Uchiha Sasuke
Sai was assigned by Shimura Danzo to assassinate Uchiha Sasuke, who had recently been named a threat to Konoha in the Bingo Book. As a result, Sai was placed on the same team as Naruto and Sakura, who had begun their mission to find evidence of Sasuke's whereabouts. Initially, Sai was ready and willing to carry out his mission, but due to Naruto and Sakura's desire to save Sasuke, he was inspired to meet Sasuke and convince him to return to Konoha without bringing him any harm. When they finally met, Sai politely greeted him while Sasuke referred to him as a "loser" and used genjutsu to scare him. Later, Sai spoke of his desire to remind Sasuke of his former bonds, but this irritated Sasuke and he attacked him. Therefore Sasuke fled after a scuffle with his former teammate.

Despite detesting Sasuke and labeling him a traitor, Sai tried to be supportive of Naruto and Sakura's goal to retrieve Sasuke. As Sasuke began committing more crimes to the point where he aligned with the Akatsuki, Sai concluded saving Sasuke was a lost cause. He even expressed anger at himself for causing Naruto and Sakura pain, and felt it was best to eliminate Sasuke before he dragged the nations into a war. However, Sai informs Naruto of his friends' decision to get rid of Sasuke, and Naruto convinces them to change their minds.

During the war, Sai was shocked when Sasuke showed up on the battlefield to help the Allied Forces. However, Sai said Sasuke, as a criminal, can not be trusted as a comrade. Despite this, Sai was willing to fight along side with Sasuke if it meant gaining an advantage to take down the Ten-Tails, and help the injured shinobi. Sai even teamed up with Sasuke to ambush Madara right after the latter was resurrected. Towards the end, Sai fell victim to the Infinite Tsukuyomi and was freed by Naruto and a redeemed Sasuke.

After the war, Sai forgives Sasuke and accepts him as a comrade. Although Sasuke still dislikes him, he puts up with Sai for Naruto and Sakura's sake. While Sasuke travels the world, he and Sai stay in contact and exchange information on potential threats to Konoha.

Hatake Kakashi
When Sai was assigned to Team Kakashi, Sai never met Hatake Kakashi because he was bed ridden from his mission. Which led for his friend Yamato to take his place for the mission to catch Orochimaru's spy. Even though the mission was a failure because Sasuke escaped again. Sai was still eager to meet Kakashi, since he admires the former due to Kakashi's past as an ANBU captain. When they first met, Kakashi welcomed Sai to the team, and the two instantly got along. Sai has great respect for Kakashi, and considers him to be a true shinobi and leader.

Knownable Relatives

 * Shin (Adopted Older Brother/dead)
 * Yamanaka Ino (Wife)
 * Yamanaka Inojin (Son)
 * Ino's mother (Mother in law)
 * Yamanaka Inoichi (Father in law/dead)
 * Uzumaki Naruto (Best Friend/Teammate)
 * Haruno Sakura (Friend/Teammate)
 * Uchiha Sasuke (Friend/Teammate)
 * Hatake Kakashi (Sensei/Friend)

Trivia
According to the databook(s):
 * Sai's name is most likely based off of the kanji (才) meaning "ability, gift, genius, talent, or aptitude".
 * In a ova for Naruto Shippuuden episode 95, it is unknown how many bowls of ramen Sai can eat.
 * As an ANBU member, Sai refers to Kakashi as his Senpai out of respect.
 * Between the end of the Fourth Shinobi War and the events of The Last: Naruto the Movie, Sai changes his rank from "Anbu" to Chubu (柱部). The word chubu means Support Division. Currently, it is not known what exactly this change implies.
 * His birthday is November 25, & his bloodtype is A.
 * Sai's hobbies are drawing & calligraphy.
 * Sai wishes to fight Hatake Kakashi.
 * Sai's favorite word is "Comrades" (仲間).
 * Sai's favorite food is momen tofu. While his least favorite 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.
 * In Tsunade's Infinite Tsukuyomi dream. Sai was part of Root and was one of its best members, alongside Uzuki Yugao, Gekko Hayate, and Mitarashi Anko. He wore a standard-issue Anbu uniform with a black hooded cloak and a mask with abstract symmetrical designs.
 * Sai is the only known male character in the series to take on his spouse's surname upon marriage.

Voice Actors
all information on Sai came from http://naruto.wikia.com/wiki/Sai
 * Japanese : Satoshi Hino (2007 – Present)
 * English : Benjamin Diskin (2009 – Present)