Itachi Shinden: Book of Dark Night

is an original story written by Takashi Yano and illustrated by Masashi Kishimoto. It is the second instalment of the Naruto Shinden series.

The two Itachi Shinden novels received a loose adaptation for the Naruto: Shippūden anime: Itachi Shinden Book: Light and Darkness.

Chapter 4
At age eleven, Itachi Uchiha is given the assignment to assassinate Mukai Kohinata - a traitor to Konohagakure - before he can join the village's Anbu. The day before the mission is to take place, Itachi practices shurikenjutsu while his younger brother, Sasuke, watches. When they return home they find their father, Fugaku, waiting for them. Fugaku offers to accompany Itachi on his mission in order to guarantee its success, unaware that Itachi has already secured the assistance of his best friend, Shisui Uchiha. Itachi does not reveal this, instead declining because Sasuke will be joining the Ninja Academy the next day and it is important to Sasuke that Fugaku be there for him. Fugaku tries to insist on helping Itachi, causing Itachi to insist on Sasuke's happiness. Fugaku relents, unwilling to risk jeopardizing Itachi's mission because of how important his membership in the Anbu is to the Uchiha clan's plans to overthrow Konoha.

The next day, Itachi and Shisui follow Mukai's movements around Konoha, watching as he leaves a shadow clone in the village to keep up appearances for him while he meets with his Kirigakure-contacts. Itachi and Shisui follow him to his rendezvous location, defeat the Kiri-nin waiting there, and then turn their attentions to Mukai. Mukai refuses their offer to surrender, prompting Shisui to attack him. Despite his considerable talents, Shisui is unable to land a blow against Mukai's Gentle Fist and Byakugan. In truth, Shisui's attacks are all feints, meant first to distract Mukai while Itachi conceals himself and then to trick Mukai into making eye contact with the hidden Itachi's Sharingan, thus trapping him in a genjutsu.

Mukai is too experienced to fall for their ploy, and as soon as he lets on that he knows what they're up to he starts attacking Itachi with Eight Trigrams Sixty-Four Palms. Shisui interrupts the attack, but Mukai catches him by the neck and begins crushing his throat. Though he has difficulty moving because of Mukai's attack, Itachi tries to use a genjutsu on Mukai, only to find it is too weak. In response, Shisui activates his Mangekyō Sharingan, successfully catching Mukai in a stronger genjutsu. To their surprise, Mukai immediately cuts open his own stomach, a command he'd placed on himself in case he ever fell prey to genjutsu. Before he dies, Mukai confesses to his crimes so that his family in Konoha will not be persecuted for anything he did.

With the mission accomplished, Itachi is accepted into the Anbu. He requests to be added to Team Ro under the leadership of Kakashi Hatake, which Danzō Shimura agrees to. Danzō also assigns one of his Root-agents - a masked man codenamed Sugaru - to Team Ro with the specific task of protecting Itachi. Itachi does not feel he needs protection, but Danzō alludes to how others might react if anything happened to him. Itachi realizes that the Uchiha, already so angry with Konoha, could very easily use his death as a pretense to take action against the village; he does not argue against Sugaru's assignment. As he returns home afterwards, he runs into Izumi Uchiha, a friend from his days in the Academy who has recently become a ninja herself. She congratulates him for joining the Anbu, but shares her concerns over the direction he's taking. Itachi can do nothing but stand with her until her concerns pass.

Upon joining Team Ro, Itachi finds Kakashi's title of "Friend-Killer" to be undeserved, as Kakashi is very kind to him and a model leader. When, at the clan's next meeting, he is asked about the Anbu, Itachi can honestly that there is no systemic prejudice against the Uchiha. Individuals may have prejudices and jealousies, but as much is to be expected. Fugaku and the other Uchiha choose to latch to the latter fact rather than the former, and become upset when Itachi tries pointing out their invention of conflict. Shisui speaks with Itachi after the meeting and informs him that he's been given permission by the Third Hokage to try to end the Uchiha's planned coup, in effect making him an Anbu like Itachi. Itachi agrees to help him.

Itachi is soon introduced to Team Ro's ongoing assignment: constant monitoring of the entire Uchiha compound via hidden cameras. Itachi decides the best way to avoid a coup is to never tell the Uchiha about the surveillance. During his shift at the monitors, Itachi does not watch any one feed for long, not wishing to intrude on his clansmen's lives more than necessary. Despite how quickly he switches views, Itachi does well at task, even catching the imperceptible signs of a disturbance at the Naka Shrine caused by the masked man. Itachi considered the possibility that the man was an Uchiha when they met years ago, but his presence at the Naka Shrine seems to confirm it. When trying to guess who the man is behind his mask, Itachi decides it could only be someone reported dead but whose body the clan never recovered; Madara Uchiha is the only such person he knows of. He keeps this discovery from the other Anbu.

Chapter 5
After several months with the Anbu, Itachi is part of a team assigned to observe a discussed alliance between Konoha and the Land of Frost. The Frost-ninja end up killing their Konoha counterparts, prompting Itachi and the other Anbu to retaliate. Although Itachi does not mind killing those directly responsible for the Konoha-nin's deaths, he tries to let the others escape. All are cut down by Kakashi, Sugaru, and Tenzō. Afterwards, Itachi laments that, despite all his strength, he still is no closer to achieving his childhood dream of ending conflict. If he is never to be successful, he would prefer to stop being an Anbu, but knows that would never be allowed.

His frustrations with the Uchiha continue to grow: during meetings, he tries to tell them nothing so that they will not find excuses to feel wronged, but this only causes many of the Uchiha to become suspicious. His only outlet are the brief moments he can spend with Sasuke. Sasuke excels in the Academy and for that reason has no friends, the same experience Itachi had. Unlike Itachi, Sasuke is constantly bothered by Naruto Uzumaki; Itachi feels that Naruto only wants to get to know Sasuke and suggests they become friends, to Sasuke's horror. Sensing the pressures weighing on Itachi, Fugaku tells him to do what he thinks is best, even if that means disagreeing with the rest of the clan. Itachi vows to never let anyone else make decisions about his life, filling Fugaku with guiltless pride for the first time in a long time.

Shisui calls Itachi to a secret meeting in the middle of the night. Itachi navigates out of the Uchiha's compound using the monitoring cameras' blindspots, which he's previously taught Shisui about. When he arrives, he finds Shisui tired and clearly overworked. Itachi apologizes that he hasn't been able to help like he'd promised, but Shisui does not blame him since Itachi has responsibilities to the Anbu. Shisui informs him that the clan suspects him and that they've ordered Shisui to spy on him; he makes clear that this order did not come from Fugaku. Because the clan is to vote on the coup at their next meeting, and because the consensus is expected to be in favor, Shisui believes they must intervene.

Shisui proposes using his Mangekyō Sharingan's ability, Kotoamatsukami, on Fugaku to change his mind and make him oppose the coup. As the coup's ringleader, Fugaku will undoubtedly sway the clan in the end. However, Shisui anticipates that the coup's most ardent supporters will try to blame Itachi for Fugaku's change of heart if he's there, and so asks that he not attend. Itachi agrees. He informs his father and mother of his planned absence the following night; it is only now that it occurs to Itachi that his mother would naturally support Fugaku's plans. Fugaku is angered by Itachi's decision and begins pressing him on his reasons. Rather than be drawn into an argument, Itachi brings attention to the fact that Sasuke is eavesdropping, abruptly ending the discussion.

Shisui plans to use Kotoamatsukami on Fugaku immediately before the Uchiha's meeting. He is summoned before Danzō shortly before this is to happen, where Danzō reveals that he already knows of Shisui's plans. He explains that changing Fugaku's mind will only postpone the coup, as there are too many who support it. Shisui begins arguing that it's worth the effort when Danzō cuts him off, stating he could make much better use of Shisui's Mangekyō. By the time Shisui realizes what Danzō intends, he has already been paralyzed by Sugaru's insects. The insects' poison will kill Shisui in a short while, giving Danzō time to take his eyes. He plucks Shisui's right eye, but Shisui escapes before his left eye can be taken. Danzō orders Sugaru and the other Root agents to kill him, fearful about what Itachi might do if Shisui speaks to him.

Itachi waits for Shisui at the same location as their previous conversation. He expects it will be a few hours until Shisui arrives, so is therefore surprised when Shisui appears before the Uchiha's meeting has even started. Shisui reports his failure: that he could not use Kotoamatsukami on Fugaku due to Danzō's interference and that the coup is now unavoidable. Itachi is now the last hope. Shisui entrusts his remaining eye to Itachi in case it will prove useful and so that Danzō cannot have it; he calls on a passing crow, implants his eye within it, and instructs it to follow Itachi. Shisui explains that he awakened his Mangekyō by killing his closest friend: shortly after the Third Shinobi World War ended, he and the friend were on a mission that was much too difficult for genin as they were. While being pursued by enemy forces, the friend fell behind, and Shisui did not make the effort to save him.

While Shisui may not have literally killed the friend, he confesses he'd been jealous of the boy's abilities and that that jealousy motivated his refusal to help. The guilt he felt was enough to awaken the Mangekyō. Shisui reiterates that he will die from Sugaru's poison, making this the perfect opportunity for Itachi to kill him and gain Mangekyō of his own. Itachi understands and begins to approach Shisui, doing his best to keep his tears at bay. Shisui confides to Itachi that he believes Itachi's abilities are great enough to change that world, that he is glad to have met Itachi, and that he trusts him to handle the rest. Once Shisui is dead, Itachi feels the Mangekyō's power pulsing within his eyes, which he vows to use to stop the clan.

Chapter 6
The day after Shisui's death, Itachi talks with Sasuke. Although he's distracted by the events of the previous night, Itachi notices that Sasuke is now jealous of the attention he receives from Fugaku. Itachi remarks that it's probably for the best that Sasuke hate him. Sasuke tries to reassure Itachi that he has no ill-feelings, but they are interrupted by the arrival of Inabi, Tekka, and Yashiro Uchiha, major conspirators of the clan's coup. The three inform him of Shisui's apparent suicide, but do not hide their suspicions that Itachi killed him. Already upset by Shisui's death, Itachi becomes enraged that they have missed the call to stop the coup in Shisui's suicide note, which he dictated to Itachi before he died.

Itachi attacks them, earning a reprimand from Fugaku when he arrives on the scene. Itachi contemplates killing all four of them, being a quick and effective means to his dreams of peace. Sasuke pleas for Itachi to stop and Itachi complies, remorseful about what he almost did in Sasuke's presence. Although Itachi apologizes for his actions, it is now clear to Fugaku that Itachi has sided with Konoha. The coup cannot succeed without Itachi's support, but Fugaku does not know how he can change Itachi's mind, or even if he should. Izumi later stops by their home looking for Itachi, so Fugaku asks that she give Itachi the support that Fugaku wishes he was able to.

At age twelve, Itachi is promoted to Anbu captain so that he will be able to focus on resolving the Uchiha's conflict in the same way that Shisui was. The Third Hokage wishes to object because of his unofficial rule that Anbu captains be at least thirteen, but is swayed by Danzō's suggestion that they falsify Itachi's age in official documents. Danzō later informs Itachi of all this, careful to present it as being the best way for them to help the Uchiha. Itachi bluntly asks why Danzō killed Shisui, so Danzō repeats what he told Shisui: Shisui's plan would have solved nothing. Danzō proceeds to voice other methods Itachi might try, but explains why each would ultimately be a disservice to Konoha. Itachi attempts to leave rather than listen to him, which Danzō interprets as proof that he already knows the one solution that will work: the Uchiha must be exterminated since the coup cannot be averted, and it must be done by an Uchiha since any appearance that Konoha was involved would incite the village's other clans into rebellion.

Sugaru approaches Itachi as he leaves the meeting with Danzō. He reveals himself as Yōji Aburame, who was briefly teamed with Itachi when he was a genin; he has been monitoring Itachi on Danzō's orders since the day Itachi entered the Academy. Guessing that Itachi wants to kill Danzō, Sugaru advises against it, explaining that Danzō has taken sole responsibility for doing too many deplorable things for the sake of Konoha. As one example, Sugaru explains that Danzō leaked to the village that Naruto Uzumaki is the jinchūriki of the Nine-Tails, giving the villagers somebody to direct their hatred towards after the Nine-Tailed Demon Fox's Attack which, in turn, helped them recover from that crisis. Until Itachi is prepared to perform such acts as often as Danzō does, killing him would harm Konoha.

Itachi spends the next year gathering intelligence on the Uchiha. Because the clan no longer trusts him and because he no longer attends its meetings, he relies almost exclusively on what he learns from the surveillance footage. Gozu and Mezu, two members of Root who alternate duties of impersonating Kagen Uchiha and who thus are better informed, tell Itachi that the clan will decide a date for the coup at their next meeting. Itachi attends the meeting and tries to convince the clan to stop the coup, as they are grossly overestimating their strength relative to Konoha's. Fugaku states simply that what he does he does for the futures of Itachi, Sasuke, and their children. Itachi argues that this course will only destroy their futures, causing the clan to expel him from the room. Izumi follows Itachi and encourages him to keep trying to reason with the Uchiha, but he replies that it's too late.

Itachi informs the Third Hokage and the Konoha Council that the Uchiha have decided to begin the coup in ten days. He is silently enraged that the Third is surprised by this and begins to feel that this time that was bought by Shisui's death has been wasted. The Third asks Itachi to delay the clan as best he can while the Third reaches out to them, leading Itachi to wonder why the Third is only now willing to get involved, having been previously content to leave the matter to others. Danzō meets with Itachi afterwards and tells him what he already knows: that the Third won't be able to accomplish anything and will inevitably side against the Uchiha. Danzō repeats his previous proposal that Itachi wipe out the Uchiha before they can act. Although tormented by the knowledge that Shisui would disapprove, Itachi accepts Danzō's assignment, remembering Fugaku's encouragement to not let his actions be determined by others.

Itachi begins watching the Naka Shrine. When, one night, he sees Yashiro Uchiha exit the shrine alone, Itachi sneaks in and finds the masked man there. He addresses the man as Madara Uchiha, revealing that he knows of Madara's decades-old vendetta against both Konoha and the Uchiha. The man does not deny any of this. Because the man's current efforts to have the Uchiha destroy Konoha cannot possibly succeed, Itachi proposes that the man join him in wiping out the clan. The man confesses he has no attachment to the planned coup and that it was merely one of a variety of projects he could have spent his time on. Intrigued by Itachi's proposal, the man agrees both to help him and to leave Sasuke alone, a condition that Itachi insists upon.

The Uchiha Clan Downfall is to take place the night before the Uchiha's coup, as it is expected that most of the clan will stay within the compound to rest in preparation for the coup. Danzō arranges for the Military Police Force's headquarters to be renovated on the same night, ensuring that those Uchiha who would be on duty will also be in their homes. Danzō also sees to it that Sasuke will be delayed at the Academy until late, allowing him alone to be spared from the Uchiha clan's demise. When his mission starts, Itachi makes Izumi his first target. He uses Tsukuyomi on her, causing her to experience in mere moments a long and happy life with Itachi. When she dies of natural causes within Tsukuyomi's illusion, her body is tricked into expiring as well.

Itachi and the masked man make plans to move through the compound from opposite ends. Itachi volunteers to deal with as many of the women and children as possible, but the man advises against it since Itachi is already burdening himself with enough sinister deeds. The man also points out that his ability makes him best suited for dealing with targets likely to scream. Itachi agrees. Itachi kills most of his targets quickly and painlessly, but gives those such as Inabi and Tekka opportunities to fight back. Mezu, currently in disguise as Kagen Uchiha, offers no resistance, well aware that Kagen's body must be among the dead. Itachi takes care to prolong the suffering of Yashiro Uchiha, considering him to be the clan's biggest coward for using others to do his dirty work: forcing Fugaku to be leader of the coup and ordering Shisui to spy on Itachi.

When all the Uchiha except for his parents are dead, Itachi pauses in his mission and watches the entrance into the compound. He sees Sasuke returning home and basks in Sasuke's last moments of innocence before he discovers what has happened. Itachi hurries home ahead of Sasuke and finds his mother and father waiting calmly for him. They do not fight him, nor do they accept his apology, as they are proud to have raised a son so willing to do what he believes is right. Fugaku feels that it is Itachi who is owed an apology, as the clan's actions have driven him to this act that he will never be able to forgive himself for; Fugaku regrets that he did not trust Itachi more, as he believes Itachi, being so gifted, could have someday have become Hokage, thus reuniting Konoha and the Uchiha. Before he kills them, his mother and father ask only that he look after Sasuke.

When Sasuke returns home and finds Itachi standing over their parents' bodies, Itachi initiates a plan he has set forth for him: to provoke Sasuke into grow up hating Itachi, gaining enough power to someday kill him and avenge their family, in the process becoming a hero in the eyes of Konoha. Itachi agonizes over the things he must say and do to sever Sasuke's love for him and drive him along this intended path, but he manages to accomplish it. He is so successful that Sasuke immediately takes action against him, using all of his energy and willpower to pursue and attack him. Sasuke can only manage to damage Itachi's forehead protector before he escapes into the night, but Itachi fears Sasuke might also have noticed him crying, which would ruin everything.

Only an hour after Itachi completes the mission, Danzō begins leading the collection of the Uchiha's bodies. He is approached by who he thinks is Gozu, but actually turns out to be Itachi wearing Gozu's clothes and mask. Itachi warns Danzō to do nothing to Sasuke, otherwise he will share every secret he knows with Konoha's enemies. Itachi also meets with the Third Hokage, who has stripped Danzō of all his authority for what he drove Itachi to do. Itachi asks that the Third do everything he can to look after Sasuke. He also informs the Third that, in his continuing service to Konoha, he will be investigating an organization called Akatsuki. Sugaru follows Itachi as he finally leaves the village, having instructions from Danzō to continue watching him. Itachi uses Tsukuyomi on the bugs inhabiting Sugaru's body, preventing him from moving and making him an easy target for Amaterasu, vengeance for Shisui.

News of Itachi's actions spreads quickly throughout Konoha and he is labeled an unprecedented traitor. Shinko Inari and Himuka Suzukaze, former teammates of Itachi's, are particularly saddened by what he's done, having a hard time reconciling what he did with the kind boy they once knew. With his infamy only going to continue to spread, Itachi approaches the masked man about what options are available to a criminal such as himself. The man arranges a meeting with Orochimaru, another traitor to Konoha. Although Orochimaru is far more familiar with Itachi than he has any reason to be, Orochimaru feels that what Itachi has gone through has exposed him to the hypocritical peace of the world, making him perfect for Akatsuki. Orochimaru leaves them, the masked man escorts Itachi to Amegakure, and Shisui's crow follows from high above.

Years later, after the defeat of Kaguya Ōtsutsuki but before the Infinite Tsukuyomi is to be brought to an end, Sasuke reflects on the events of Itachi's life. He finds merit in Itachi's decision to take the world's evils upon himself in the name of peace. Ultimately, Sasuke decides that he will follow Itachi's example, bringing about a revolution.