The arc comes to a close. Takasugi vs Oboro and Oboro's past is revealed.
Umibouzu stands in a field of flowers with Kouka also standing across from him. Seeing her confirms for him his own demise and he walks towards her. Stopped by a chasm between them, he recognizes that his wife still believes that there was something for him to do but the hunter admits that he can no longer hold or discipline his children thanks to his armless state. He pleads to her retreating figure on what should he do. He awakens from his dream to find himself in a sick-bay room in the Kaientai's Kaienmaru. A voice nearby speaks about Umibouzu's tendency to survive dangerous and deadly situation and then later talking about them to her. The voice, Mutsu, wishes to know about this latest interesting tale; the older Yato counters if she minded if the story was just complaining.
Mutsu then recites what happened after he was taken away from the fight with his son by Sadaharu. The defeated Kamui lays on Kagura's lap while the injured Shinpachi, Gintoki, and Abuto watch on. The Yato vice-commander was annoyed that the Yato siblings were passed out while they wanted to as well and Gintoki wholeheartedly agrees. They then find themselves surrounded by the Harusame and prepare themselves to fight. But the injured Shoukoku stops them and the equally injured Batou reveals that they and some of the Harsame were abandoned by Utsuro after losing against the humans; Abuto counters that they abandoned Utsuro. The monkey Amanto admits he never liked the immortal and believed him to be a poor example of a pirate; the humans looked more free-spirited and interesting. Batou then wonders if Kamui, the Harusame's "Thunderbolt", was okay; Abuto wasn't sure if the figure before him was his boss or a sibling but remarks that the teen was never one to stay down even after being defeated. Kamui raises an arm to Abuto and declares that he will never lose again to anyone. As Abuto picks him up and they and the rest of the Harusame remnant leave, Kamui states that he had spent far longer as a "pirate" than as a "son" or "big brother" and plans on continuing moving forward, to the point where his sister can't reach him, he surpassed his father and will be able to reach his mother. It will be at that point that he will be able to catch up and return.
After hearing the tale, Umibouzu admits that despite their resolve in wanting to kill each other, he and Kamui weren't able to do so, thanks to their familial bonds. He and Kamui never needed to try to cut those ties since they can't be cut; they instead needed to bring these ties closer, through both good and bad times. He thanks Kagura and her Yorozuya bonds for making him realize this and for not letting go of her family ties. Kagura quietly overhears her father's talk before walking into the ship's deck where Shinpachi, Gintoki, and Sadaharu stood. She apologizes for acting selfishly as she didn't want the males to be involved. Gintoki interrupts by wondering what kind of place Kagura's hometown was but answers that it was similar to Kabukichou, then tells her to put the envelope in her hand away. Shinpachi adds that they knew she can't leave her father but they won't accept the resignation letter; they will instead accept a leave letter and will wait for her to come visit them.... Except Kagura shows that the envelope was actually a paid leave letter, a request to add pay into their holiday; Gintoki, Shinpachi, and Sadaharu throw Kagura into the ocean in retaliation. She berates them for throwing her and tells them that it was for frivolous expenses and medical bills for Umibouzu. Gintoki counters that Umibouzu will be fine, though his hair was still a lost cause. Suddenly, he and Shinpachi are attacked from behind by a missile (Sadaharu jumps out the way). The perpetrator was Umibouzu in a wheelchair, carted by Mutsu. He was testing out his new mechanical arms then continues to maliciously blast the two humans, letting Mutsu know to send the bill to the Yorozuya. On the docks, Sakamoto and Katsura overhears the explosions and the Kaientai leader declares that his ship's damage will be billed to the Yorozuya, too. Three people stop on the docks in front of them and Sakamoto asks them, the Kiheitai members, what happened after the three of them separated. One of the men, Takechi, answers he had a message from his boss.
When Takasugi, Sakamoto, Katsura and their groups separated (and Sadaharu was running with Umibouzu), the Kiheitai continues to fend off Naraku's persistent attacks. Takechi notes that they were separated from the others but Takasugi states they were never allies to begin with, he was already indebted to them for saving him and he will return the favor someday. But he must deal with one other person first; the group runs towards a clearing where on top of a ruined building stands Oboro. He thanks the assassins for leading them to his location but commands them to retreat as the Harusame was doing so too and they do so. Matoko wonders what was happening yet the Naraku leader admits that their survival was unexpected but didn't change Utsuro's plans at all as they, the "insects", mean nothing to him. Takasugi wonders why Oboro was here and Oboro responds that he knew that insects will never give up and will continue to fly until reaching the heavens; after all, he gained the same wings as them through the same man. Slightly surprised, Takasugi insists that Shouyou was dead and the person responsible for his death was in front of him. The two pull out their swords as Oboro declares that he will use the last of his life to pluck Takasugi's "wings".
In the past, a child hides quietly in a storage shed, the only survivor of a household massacre. The perpetrators, the Naraku, then finds and fatally wounds him while setting the building on fire. The child, Oboro crawls not far from the shed and collapses, wondering if this was death to a figure that appeared next to him, the Naraku's leader, Utsuro. Utsuro pulls out his small sword and instead of finishing Oboro off, stabs his own arm, allowing the blood to enter the child's wounds and revive him. Utsuro apologizes for being unable to die for the child's revenge, so he hoped that he will hate him forever instead. Surprisingly, Oboro decided to serve Utsuro as a thank you for reviving his meager existence until the donated blood he gained runs out. Weeks later, Utsuro tells Oboro he should leave before he will be officially trained as a killer, though the child refuses, believing him to be a great teacher that deserves respect. Utsuro refutes this, he would much rather learn to clean his blood-covered hands. Oboro suggests to open a school where student and teachers can learn together. Utsuro wonders what could he teach except killing and the child counters that Utsuro had refused to teach him assassination techniques so he wasn’t truly evil. Oboro asks to be Utsuro’s first student in his new school. In the present, Takasugi and Oboro fight but when the Naraku corners the Kiheitai leader to a wall, he thrusts his left arm at him which Takasugi barely dodges, revealing that hand to be actually mechanical.
Back in the past, Oboro learns that Utsuro has run away and must be punished. Oboro stumbles across Utsuro hidden on a tree branch. The Naraku leader admitted he had long since planned on running away but meeting Oboro gave him the push he needed to go through with it; he also did it to lure the child, his first student, away. He will atone for his sins and fight the shinigami within him. In the present, Oboro uses his fake arm for a chi thrust, knocking Takasugi down and rushing at him with his sword yet seeing Takasugi thrusting his sword at him. Oboro grabs the opponent’s blade and continue his thrust but Takasugi kicks his own sword, breaking it and continuing his thrust. In the past later that night, Utsuro gives the name of his new school, Shoka Sonjuku, referencing the two of them under the pine tree forming the school just now and a promise to have more students under the same tree. A while later, Oboro sees a group of searching Naraku down a cliff and realized that they will be caught. He hatches a plan to use himself as bait and use a trap set up by Utsuro (though it wasn’t meant to kill them) to get rid of them. He stabs himself with Utsuro’s sword and walks towards the pursuers telling them that he helped Utsuro escape but was then betrayed by him. But the assassins didn’t fall for it and stab him as Utsuro watch on; he states that Utsuro will never kill again and he will make sure of it and activated the trap. Large boulders roll down the cliff, crushing both the trackers and Oboro with Utsuro watching on. Before being crushed, the child apologizes for breaking his promise but he was happy to sacrifice his life to protect him, his future school and his future students.
Thanks to Utsuro’s blood, Oboro survives but Utsuro never realizes this at the time. He formerly joins the Naraku to make sure that they stay away from Utsuro, fully embracing being a killer. He didn’t care as he believed that he was protecting his teacher and his ideals. But when he waked past Utsuro, now Shouyou, with his three students Gintoki, Katsura, and Takasugi, he realized that he actually wanted his teacher back and he ended up reporting Utsuro’s location to the Naraku, leading to his arrest and his school being burned down. He knew though that Utsuro will return. In the present, he reveals his transgression to the downed Takasugi, admitting how similar they were, one who swore to never betray him again and the other who swore to bring him back, even if it means killing him again. Oboro pulls out Takasugi’s broken sword from his neck while Takasugi pulls out Oboro’s sword through his cheeks and rises. The two strike while the assassin notes the core strength of Shouyou’s students: to keep fighting until the spirit Shouyou gave them runs out. In the past at the moment of his execution, Shouyou walks past Oboro. He thanks all his students for making him who he was but apologizes to Oboro, wishing that Oboro and his other students have met in different circumstances.
Takasugi defeats Oboro and the man admits to seeing his junior disciples strength as he collapses. He sees that the wounds were finally fatal yet remarks that his pain was nothing compared to Utsuro’s. He asks Takasugi to listen to his information on Utsuro while at the same time, Utsuro meets with his fellow Tendoushuu.
- Kouka (cameo)
- Sakata Gintoki
- Shimura Shinpachi
- Pluto Batou
- Neptune Shoukaku
- Tenshouin Naraku
- Katsura Kotarou
- Yoshida Shouyou (flashback)
- Tendoshu (cameo)