The Bakufu is the government of Japan, which is led by the Tokugawa Shogunate, though it is in reality controlled by a council of Amanto called the Tendoshu.
Voiced by: Yuki Ono (JP), Lucas Gilbertson (EN)
Also known as the Great General, he is the ruling Shogun of Edo in the Gintama world. He is a close friend of Matsudaira.
- Butt-Monkey: It's amazing how a man who could order to execute any person he wish can achieve such big levels of humiliation and pain in just a few seconds/a few panels after his appearance. It's a record even by Gintama standards!
- Covert Pervert: Gets a nosebleed at the prospect of seeing the girls naked at the pool.
- Crouching Moron, Hidden Badass: Despite not being shown fighting, he's very honorable and would sacrifice his own position in order to make justice. Then he turns fully badass when it's revealed he's received ninja training back in his childhood.
- Died in Your Arms Tonight: Dies peacefully and smiling with his head on his unknowing sister's lap.
- Go Out with a Smile: He dies with a smile on his face.
- Historical Domain Character: His historical counterpart is Tokugawa Iemochi, who was Shogun during the Bakumatsu period. His name meanwhile, is taken from Tokugawa Ieshige—ironically one of the shoguns least-interested in his job (in contrast to Shigeshige's effort to know the affairs even of regular people).
- I Just Want to Be Normal: The main reason behind his appearances, as he tries to experience the life of a normal citizen. It always ends up badly for him.
- Kneel Before Frodo: Bows down to Kagura and Shinpachi and thanks them for helping save his retainer and father figure, Maizo.
- Naked People Are Funny: Almost constantly ends up naked. Always funny.
- Nerves of Steel: No matter what happens to him, he never loses his cool.
- Nice Guy: Compared to his uncle (and Nobunobu), he is a humble man that wants to make a difference in Edo, and at the same time, puts himself at the same level of their citizens.
- Phrase Catcher: Gintoki will often say "Shogun ka yo...!" ("It's the shogun..!") when he shows up.
- Puppet King: For his uncle Sadasada, who still ran the show behind the scenes, and the Tendoshu. He later turns against his role as puppet and openly opposes the Tendoshu's rule.
- The Quiet One: He usually lets others do the talking for him.
- Reasonable Authority Figure: He may be a Puppet King, but he has the best interests of his people in mind and tries to improve their lives to the best of his ability.
- Running Gag: Him getting naked.
- Sacrificial Lion: He is the first major recurring character to die, being killed with a poisoned needle at the end of the Shogun Assassination arc. This has major consequences in the following events.
- Screw the Rules, I'm Doing What's Right!: Surprisingly heroic during the Courtesan of a Nation arc, getting the entire police force to overthrow Sadasada and then defies the Tendoshu's orders.
- The Stoic: He always keeps up his composure as shogun, even if he is secretly crying on the inside.
- Teeny Weenie: In his first episode after he strips off all his clothes, Gintoki mentions that Shigeshige has a foot soldier instead of a shogun down there.
- The Wise Prince: Despite his young age, Shigeshige has the best intentions for his people and seems to be a legitimately competent ruler in his own right.
Princess Soyo Tokugawa
Voiced by: Ryo Hirohashi (JP), Caitlynne Medrek (EN)
Shigeshige's little sister. She occasionally sneaks out of the palace because of boredom and loneliness. She met Kagura at one time and they have been good friends ever since.
- Cheerful Child: Constantly cheerful and oblivious.
- Chekhov's Gunman: Becomes quite a pivotal character in the Courtesan of a Nation arc few hundreds chapters/around two-hundred episodes after her introduction.
- She sees no problem in sneaking into a prison for sleepover.
- She gets kidnapped and threatened with death by Joi extremists in episode 286, but remains calm the entire time because she believes the whole ordeal is simply an elaborate watermelon-smashing game.
- Cute Is Evil: She isn't really evil, but she enjoys the suffering of others if it makes herself look good.
- Forehead of Doom: She has a rather prominent forehead.
- Hime Cut: After the two-year Time Skip, Soyo has parted blunt bangs, cheek length sidelocks, and mid-back length straight hair.
- Interclass Friendship: Soyo, a princess, is best friends with Kagura, a Yato from a very poor family and currently living in Perpetual Poverty because her boss Gintoki rarely pays her a good salary.
- Lonely Rich Kid: She feels lonely in the palace, which is why she sneaks out.
- Older Than She Looks: She's apparently older than Kagura, who is 14, but just like Kagura she looks and acts like she's a couple of years younger.
- Rebellious Princess: Mild example. She likes sneaking out of the palace because she feels so trapped there, but won't put up a fight when the Shinsengumi arrive to get her back.
- Sadist: Soyo seems to have high potential as a sadist, according to both Kagura and Shinpachi. Unlike Okita she is more of a psychological sadist than a cruel fighter. And seemingly enjoys watching others in pain rather than directly causing it.
Voiced by: Takaya Hashi
Shigeshige's uncle and predecessor as Shogun. Despite having retired, he secretly controls the government from behind the scene. He made use of Suzuran's popularity, at the time Yoshiwara's highest ranking courtesan, prior to and during his reign to trap and assassinate his political rivals. He's also the one responsible for having cut off her lover Maizo's arm.
- Arc Villain: Of the Courtesan of a Nation Arc.
- Asshole Victim: He gets assassinated by Takasugi in prison.
- But for Me, It Was Tuesday: The loss of Gintoki's sensei, for him, was a traumatic experience implied to be the very reason he joined the war. For Sadasada, it was just one worm more crushed in his way to power, to the point he can't even remember his name. This might have to do with him not being personally involved in Shoyo's arrest and execution, but he's responsible nonetheless.
- Chekhov's Gunman: First appeared in flashback in the Red Spider Arc as Jiraia's original prey before he makes his actual appearance in the Courtesan of a Nation arc.
- Composite Character: Inasmuch as it is possible, there are possibly two Historical Domain Character's serving as his bases:
- Tokugawa Iesada, the predecessor shogun to Iemochi (Shigeshige's basis), providing a tangible link to the house of Tokugawa. Probably not coincidentally, the Naraku, which is operational under him, takes its full name (Tenshoin Naraku) from a homonym of the title of Iesada's Real Life wife. His reign also saw the rise of the second basis...
- Tairo Ii Naosuke, or at least a heavily negative caricature of him based on shishi prejudice and Meiji Restoration propaganda. Tairo Ii, for all intents and purposes, definitely made life hell for most rebels/opponents of the Shogunate during his heyday—which made him very unpopular and ended with his assassination.
- Corrupt Politician: Backstabbed his way to power and screws over everybody else just to stay there.
- Establishing Character Moment: When Tsukuyo confronts him about reuniting with Suzuran again, were those tears from his face due to him not seeing her in a long time? No. That was actually drool from the memories of her hands stained in blood by his corrupt takeover as Shogun and wanting to suck them again. From that point on, we look into his history and what had his actions resulted in the past that made him the most evil villain in the series to date.
- Evil Gloating: Constantly, when Gintoki and his friends come looking for Maizo.
- Evil Is Petty: Really? You're going to have Suzuran killed just to prevent Maizo from meeting with Suzuran again, for no other reason than to get the last laugh after being ousted from your position?
- Evil Old Folks: He's as despicable in his old age as he was in his youth.
- Evil Prince: In the past, having ascended to the position of Shogun by murdering his rivals to the position.
- Evil Uncle: He is Soyo's and Shigeshige's uncle, but has little to no good intentions to do with them.
- Fat Bastard: A despicable and fat monster of a man.
- Faux Affably Evil: He acts politely in front of others, but his speech is just dripping mockery and venom.
- Hate Sink: Virtually everything he does makes him more and more despicable.
- Humiliation Conga: Gets ousted from his position, pinned to a wall by his arms and crotch by Tsukuyo, accidentally beaten up and poisoned by Oboro, before getting arrested and then murdered by Takasugi in prison. He had it all coming.
- It's All About Me: All that matters to Sadasada is that he stays in power and that everybody submit themselves to his authority.
- I Was Quite a Looker: He looked much like a meaner Shigeshige in his youth, though his eyes were shadowed.
- Jerkass: Cruel and sadistic. Even Takasugi isn't as assholish as he is.
- Karmic Death: As pointed out by Okita. He built up his power base and attained his position through assassination and was ultimately assassinated in prison. The assassin, Takasugi, was even one of Shoyo's students to boot.
- Kick the Dog: Several.
- He cut off Maizo's left arm and prevented him from meeting with Suzuran forever. He later has his other arm cut off as well when he learns Suzuran is alive.
- He mocks Shouyo Yoshida's way of life and sacrifice right in front of Gintoki.
- Laser-Guided Karma: The Courtesan of a Nation Arc is basically a long overdue string of karma finally catching up to him.
- Cutting off Maizo's arm for disloyalty and preventing him to meet with Suzuran again? Gintoki and his friends' attempt to reunite the two lead to him being ousted from his position.
- Proclaiming his intent to have the Naraku take over Yoshiwara and kill Suzuran just to spite them? Tsukuyo, the law in Yoshiwara, pins him to a wall with kunai by his arms and a pointy staff between his legs.
- Ordering Shoyo's arrest and execution for very vague and minor reasons? Takasugi, one of Shoyo's students, murders him in his prison cell. Though he later turns out to have less to do with Shoyo's death than intially thought.
- Man Behind the Man: He still controls the nation through the Shogun Shigeshige, though he himself is being controlled by the Tendoshu.
- Non-Action Big Bad: Never fights physically, instead letting the Naraku do all the dirty work.
- Smug Snake: He's a competent manipulator and backstabber, but his petty desires and vile actions ensure everybody turn against him to oust him from power. Appropriately, he completely loses his cool when his plans fall apart.
- Villainous Breakdown: As his plans fall apart, he devolves into shouting and raging against the people that ousted him from power.
- Villain with Good Publicity: As the former shogun he still has a lot of power.
Voiced by: Daisuke Namikawa (JP), Giles Panton (EN)
Member of the Hitotsubashi branch of the Tokugawa Clan and their candidate for the position of Shogun. His claim is supported by high-ranking members of the Bakufu called the Hitotsubashi faction. By the time of his actual appearance, he has pretty much been confirmed for next in line for the position.
- 0% Approval Rating: His approval among his minions is in tatters by the Battle On Rakuyo Arc, which comes back to bite him as several of them leave him behind in a critical moment. Even Hankei calls him out on this, causing him to realize where he went wrong.
- The Atoner: After his close encounter with Hankei, he switches sides and starts working to undo all the bad things he's done, but is well aware he will probably never be forgiven.
- Badass Longcoat: Wears a rather cool long coat.
- Big Bad Wannabe: When it comes to his alliance with Takasugi, he seems to consider himself equal if not superior to him, but in reality he's just being used by Takasugi. Even when he betrays the Kiheitai and becomes Shogun, he's just a puppet for the Tendoshu and Isaburo.
- Butt-Monkey: Of a karmic sort. He seems to have a tendency to get himself punched into a wall.
- He spends the negotiations with the Altana Liberation Army wanting to use the bathroom thanks to Kagura spiking his food with excessive seasonings as her way of payback.
- End of an Age: As he dies, he verbally put an end to the Shogun system knowing that the people are strong enough to lead the nation without the Shogun. Just as evidenced of electing their First Prime Minister of Japan in the timeskip.
- Evil Counterpart: He is the complete opposite of Shigeshige. Especially as the Shogun, where he freely uses the privilege of executing anyone he wants. And while he and Shigeshige are punchable, Nobunobu's case is karmic.
- Evil Is Petty: Really, Nobunobu. You have the Mimawarigumi cut down two innocent hostesses out of dissatisfaction... just because they reminded you of Shigeshige?
- Faux Affably Evil: He addresses others civilly, but with a clear hint of mockery and arrogance below the surface.
- Hate Sink: His Jerkass behavior and sadism have done him well in earning the hatred of both the characters and the audience. However, he later seems to realise where he went wrong through his interactions with Sakamoto and his encounter with Hankei.
- HeelFace Turn: After his talks with Sakamoto and his close encounter with Hankei, Nobunobu finally realises where he went wrong and switches sides. To the point where both Sakamoto and Katsura present him as the Shogun during a meeting with the Anti-Tendoshu Alliance.
- Historical Domain Character: He's based on Tokugawa Yoshinobu, the last Shogun.
- Humiliation Conga: After finally becoming Shogun, he is the victim of a long string of humiliations.
- After having two hostesses cut down in the Snack Smile cabaret club, he tries to slowly cut into Tae's neck with a sword, but ends up getting knocked out by Gintoki with a single punch.
- At the end of the Farewell Shinsengumi Arc, he loses both the Shinsengumi and Mimawarigumi as police forces and other police forces end up defecting.
- Then when he attempts to stop Gintoki and the others from leaving Earth, they immediately ambush and capture him, and afterwards humiliate him in front of his retainers. When he orders all retainers to kill themselves for failing to protect him, he gets knocked out in one punch by Bansai, breaking his two front teeth, while his own forces end up leaving him with the rebels.
- It's All About Me: He wants to lead the new era as the Shogun by changing Edo to his image. By that, he means getting rid of anyone who speaks ill about him and his mandate or support Shigeshige instead of him.
- Jerkass: Has little regard for anybody, mocking people and belittling them as he sees fit.
- Kick the Dog: His actions get worse as the series progresses. The most notable event would be the entire ruckus he causes at the Snack Smile cabaret club, where he not only threatens to make Hijikata the security for Kondo's execution and has two innocent hostesses slashed up, he also puts a sword to Tae's throat while smiling in satisfaction.
- Knight Templar: Like Takasugi, he appears to believe the country is corrupt and beyond repair, and has similar intentions of destroying it, only to rebuild it in his own image. This is subverted once he actually becomes Shogun. He's not pursuing an ideal, he just wants to stay in power and do with it what he wants.
- Not So Stoic: As soon as he gets what he wants, the stoic demeanor is replaced by angry shouting and smug smiles, along with several expressions of sadistic pleasures.
- Odd Friendship: His interactions with and growing respect towards Sakamoto of all peoplenote actually triggers Nobunobu's HeelFace Turn.
- Puppet King: Takasugi plans to install him as one. He later takes up the Tendoshu's offer and becomes their puppet instead without a single regret.
- Redemption Equals Death: Takes a bullet through the heart while talking down the Altana Liberation Army from pulling a last-ditch attack on Earth—ironically the same bullet that takes Prince Enshou's life. His Final Speech encourages both sides—Earthling and Amanto alike—to end the conflict and focus on the real enemy at hand, before joining up with the spirits of Shigeshige and the other past shoguns of Japan.
- Sadist: He takes pleasure in slowly cutting into someone's neck with a sword.
- Sadistic Choice: He proposes for Hijikata to be part of the security for Kondo's execution, and if he sheds a tear, he will be forced to be the security of his comrades' execution... only as a test of loyalty. And entertainment.
- Slasher Smile: He sports a horrific grin when he has his sharp blade pressing into Otae's neck!
- Smug Snake: Arrogant and very confident in his own plans, but in reality he's just a tool for Takasugi to take down the Bakufu. He turns out to be even worse after he betrays the Kiheitai to the Tendoshu.
- The Stoic: When he first shows up, he appears to be calm, reserved and stone-faced. It doesn't last long...
- Tyrant Takes the Helm: He orders Kondo and Matsudaira to be executed for Shigeshige's death when it is obvious that the Tendoshu had a part in it. He also runs around town and has innocent people cut down for reminding him of his predecessor, while also promising to tear down everything he represented.
- Well-Intentioned Extremist: Like Takasugi, he seemingly intends to completely destroy the country, but only so that he can rebuild it into a stronger and better nation. This is later subverted, when offered the position of Shogun by the Tendoshu, he completely betrays his "allies" and their plans.
- Would Hit a Girl: He puts his blade against Otae's neck for no reason other than calling out his actions in cutting down two innocent hostess. Said women were cut down because they reminded him that Shigeshige enjoyed the club.
- You Have Failed Me:
- Cuts off Yaemons head after he loses to Gintoki and helps him and Asaemon to escape.
- After being captured by Gintoki, Sakamoto and Katsura, he attempts this again with all of his remaining forces for failing to protect him, before Bansai knocks him out and tells them he's not worth killing themselves over.
- Villainous Breakdown: Takes the news of the Mimawarigumi's defection and the Shinsengumi's rebellion less than well, ordering the police to be disbanded and reformed in anger. This backfires when it causes several of his followers to defect to the rebellion.
Officials and Retainers
Voiced by: Norio Wakamoto (JP), Kyle Jones (EN, movie)
An infrequently recurring character, as the head of national police he acts as the direct superior to the Shinsengumi and reports to the Shogun. He's often regarded as a dangerous, paranoid nutcase who resorts to violence at the first sign of provocation and sees potential assassins everywhere around him. In addition, he is extremely protective of his daughter, Kuriko, often ordering the Shinsengumi to assist him in shadowing any dates she goes on.
Although appearing to be an unstable lunatic, he is highly devoted to his job. Unlike Kondo, he is unable to sympathize with the Shinsengumi on a personal basis as he is not in direct command of them, but he holds the safety and well-being of the country and its people in high priority.
- Badass Longcoat: Wears a pretty nifty black coat.
- Bad Boss: He frequently threatens to shoot his subordinates in the face.
- Bunny-Ears Lawyer: A very quirky and nutty official who is actually competent at his job. Sometimes.
- Catch Phrase: Has a tendency to say that he'll shoot in three seconds. Then he says "One..." Then he shoots anyway. When he's protested with "What happened with two and three!?", he'll respond with "Never heard of them. A man only needs the number 1 to get through life."
- Conspiracy Theorist: Believes that people who wear sunglasses are usually assassins, even though he himself wears them in addition to other abnormal things such as the idea that righteousness is what makes up 80% of old men and the police being not more than a branch of the mafia community.
- Cool Old Guy: A competent official despite his age. When his paranoia and trigger happiness doesn't take over that is.
- Cool Shades: Nothing like shooting up terrorists with a cool pair of sunglasses.
- Crouching Moron, Hidden Badass: Paranoid nutcase. Extremely competent marksman.
- Da Chief: Of Kondo and, through him, the whole Shinsengumi.
- Dirty Old Man: As if he weren't crazy enough, drinking often reduces him to this.
- Doting Parent: Constantly dotes on his daughter Kuriko.
- The Gunslinger: More prone to using firearms than a sword when he acts directly.
- Historical Domain Character: He's based on Matsudaira Katamori, the last daimyo of Aizu who doubled as the direct supervisor of The Shinsengumi.
- Overprotective Dad: So much so that he frequently orders the Shinsengumi to assassinate any of his daughter's suitors.
- Papa Wolf: Don't mess with his daughter, as the terrorists who kidnapped Kuriko soon found out.
- Perma-Stubble: Constantly unshaven, yet it never grows beyond stubble.
- Red Baron: Known as the "God of Destruction" for his highly destructive solutions to any problem.
- Rule of Three: Parodied. He has a tendency to declare that he'll shoot something in three seconds... then shoots anyway after 1 second, because a man only needs '1' to advance in life.
- Smoking Is Cool: Though funnily enough he's one of the foremost enforcers of the smoking ban.
- Talkative Loon: The fact that he's voiced by the normally serious and cool Norio Wakamoto makes it even weirder.
- The Team Benefactor: Sort of as he's the one keeping tabs on the Shinsengumi and reports their activities to the Shogun to make sure they don't stay out of line.
- Trigger Happy: He won't hesitate to pull a gun on somebody for the most minor offenses.
- Undying Loyalty: He's completely loyal to Shigeshige, both as a subject and as a friend. Even when Nobunobu becomes the new Shogun after Shigeshige's death, he's still loyal to the deceased Shogun.
- Wave-Motion Gun: His personal flying warship is equipped with one called the "Matsu-Blaster." Probably a major contributing factor as to why he's called the "God of Destruction."
Voiced by: Shigeru Chiba (Old), Eiichiro Tokumoto (Young)
A loyal retainer of the Tokugawa Clan, noted for his service in keeping the former Shogun alive in a time of political turmoil. As proof of his loyalty, he lost his left arm in service to Sadasada.
He raised the orphaned Shigeshige and Soyo, and currently serves as Soyo's personal retainer. It is revealed that he was once Suzuran's lover and the one she made a promise to leave Yoshiwara with. Sadasada had learned of the promise and cut off the arm he made the promise with, as well as forbidding him to go see her on the pain of death for both of them.
- An Arm and a Leg: Supposedly lost his left arm long ago in service of the former Shogun. In reality Sadasada himself had it cut off when he learned of his promise to Suzuran. He later has his other arm cut off as well when he learns Suzuran is still alive!
- Big Ol' Eyebrows: As seen on his image, his eyebrows are quite big, and they were prominent even when he was young!
- Cool Old Guy: A competent and well-respected retainer of the Tokugawa Clan.
- Distressed Dude: The Yorozuya set out to rescue him and reunite him with Suzuran when they learn of his past with her.
- Grumpy Old Man: Constantly complains about Soyo's antics and what she's allowed and not allowed to do.
- In-Series Nickname: "Jiiya" (Translated as "Grampy").
- I Was Quite a Looker: Not too bad on the eyes in his youth, though he still had his big eyebrows.
- Miniature Senior Citizens: He was quite a bit taller in his youth, but has become tiny in his old age.
- Non-Action Guy: He is simply too old and is lacking an arm to be able to fight, really.
- Old Retainer: He has served the Tokugawa Clan for a long time.
- Parental Substitute: The one who raised the orphaned Shigeshige and Soyo, both of whom view him as their father figure.
- The Promise: Promised Suzuran long ago that he'd take her away from Yoshiwara with him, but due to Sadasada's interference, this is postponed until they are finally reunited just before her death.
- The Reveal: He was Suzuran's lover all along.
- Star-Crossed Lovers: With Suzuran, though they're finally reunited in the end.
- Unexplained Recovery: Maizo is heavily implied to die alongside Suzuran, with his younger self carrying her to the moon being symbolic of the two going to the afterlife together. Isaburo even outright says he will die if he goes to meet her. Despite this, he inexplicably shows up alive again more than a hundred chapters later in the Shogun Assassination arc.
Voiced by: Takeshi Watabe
Toyama is a corrupt magistrate in Edo, known for taking bribes and flaunting his wealth. He seemingly captures Elizabeth in order to lure in Katsura and kill him, which will increase his status in the Bakufu. In order to save Elizabeth, Katsura gets help from the Yorozuya and Sacchan, briefly taking ninja training and forming the group called the Go-Ninja. When they storm his mansion, they clash with Zenzo and his Shinobi Five, who have been hired by the magistrate. After the Shinobi Five and the magistrate are defeated, it's revealed that the Elizabeth he held captured was actually a fake.
- Arc Villain: He is the main villain of the short Go-Ninja arc.
- Corrupt Politician: Katsura calls him an evil magistrate who takes bribes to fill his own pockets and satisfy his desires. He only wants to eliminate Katsura to increase his own status in the Bakufu.
- Death Course: His mansion is filled with various death traps which Gintoki and Katsura power through, including wooden logs, arrows, explosives and falling roofs. In the anime, the death traps are replaced with something resembling a game show obstacle course, though still deadly.
- Non-Action Guy: He doesn't fight himself, leaving it to Zenzo and the Shinobi Five.
- Smug Snake: Arrogant, smug and completely confident that his plan to eliminate Katsura will go as planned. He quickly loses his cool when the Shinobi 5 fool around and are defeated in a humiliating manner.
- Surrounded by Idiots: He becomes exasperated with the Shinobi Five when three of them are incapacitated by poisoned curry, while Zenzo and Kaoru Waki are too busy fooling around with their opponents to fight.
- This Cannot Be!: He is incredulous after the Shinobi Five are defeated in a humiliating manner, outright saying "this can't be".
Voiced by: Satoshi Yamaguchi
An old childhood friend of Shigeshige and an official working for the Bakufu. When he learns Shigeshige is in trouble, he goes to pledge his political support.
- Childhood Friends: Shigeshige calls him a childhood friend and puts a lot of trust in him.
- Cyanide Pill: He immediately kills himself with poison after being captured.
- Face Framed in Shadow: His face is covered in shadows as he kneels and pays his respects to Shigeshige, hinting that he is up to something sinister.
- I Have Your Wife: Matsudaira speculates that his family was taken hostage, which is why he killed Shigeshige, his old childhood friend.
- Meaningful Name: His name has the kanji for "friend" in it, since he is an old childhood friend of Shigeshige.
- Poisoned Weapons: He carries a poisoned needle, which he uses to assassinate Shigeshige with when they shake hands.
- Small Role, Big Impact: He only appears for a few pages, but during those he is responsible for one of the biggest shocks in the series: Killing Shigeshige, the first major recurring character to die.
- We Hardly Knew Ye: He only appears in three pages of the manga and is revealed to have died in the next chapter.
Voiced by: Marina Inoue (JP), Carol Anne Day (EN)
A rogue member of the Ikeda Clan, which comprise a long line of sword testers and executioners for the Bakufu. She is on the run for supposedly murdering the clan's former head, who had previously adopted her. She grew up and bonded with her adoptive brother, who would eventually take on the position as the clans head and the name Yaemon. It's quickly revealed that the former head had aided a number of criminals to escape because he believed them to be innocent. The matter was handled within the clan, allowing him to commit seppuku with Asaemon as his assistant.
- Abusive Parents: Her real father was a Dirty Coward who hit her and tried to sell her to the Hitotsubashi in exchange for his own life.
- Achilles' Heel: The Ikeda style of swordsmanship is mainly used for the sake of quick and painless executions. While it's very effective in combat, the style has a critical weakness in that the user is left open after an attack, which can be exploited by making the user waste their attack.
- The Atoner: Wishes to atone for having to kill her adopted father.
- Broken Bird: Being forced to execute her father left Asaemon overcome with grief, guilt and hopelessness.
- Cain and Abel: The Abel to Yaemon's Cain.
- Cool Mask: Shaped like a skull, as Asaemon is seen as a "God of Death".
- Dark Is Not Evil: She's an executioner wearing black clothes along with a creepy skull mask, but has a kind heart.
- Death Seeker: After having to execute her own father, Asaemon left the Ikeda clan to look for a place to die. She first asked Gintoki to assist her in her seppuku and when that failed, she wanted to let the police arrest her as the Serial Killer who was murdering former criminals despite being innocent. Thanks to Gintoki's help, Asaemon recovers her will to live.
- Et Tu, Brute?: Towards her brother Yaemon when she finds out he sold her and Gintoki out to the Hitotsubashi.
- Fashionable Asymmetry: Her left sock is much longer than her right, and she wears an armwarmer on her left arm.
- Forgotten First Meeting: She met Gintoki when she was a child when he appeared before the Hitotsubashi in an attempt to get them to spare the people her father sold out, including herself.
- Happily Adopted: By the former head of the Ikeda Clan, though it didn't end happily.
- Historical Gender Flip: of Asaemon Yamada, who were actual official executioners of the Tokugawa Shogunate. More specifically, she is based on Yoshiaki Yamada, the last official executioner in the family who is famous in Japan for executing the murderers of Toshimichi Okubo and later served as a prison warden after the Meiji government enacted a new penal code that banned decapitation as death sentence.
- Iaijutsu Practitioner: Her style of swordsmanship involves quickly drawing, slashing and then sheathing the sword again in the blink of an eye.
- Implausible Fencing Powers: Most swordsmen in the series get some improbable feats, but she and her brother Yaemon take it to another level with the special techniques of the Ikeda Clan, which allows them to cut things in a way so they either stay attached or can be easily reattached. The primary use of the technique lies in executing criminals without letting their heads fall off, letting them die with some semblance of dignity.
- In the Hood: While she mostly keeps it down, she wears a hooded cloak.
- Legacy Character: Invoked, Yaemon hands over his name and leadership of the Ikeda Clan to Asaemon, as it is tradition for every head of the clan to bear the name.
- Master Swordswoman: She's an excellent master of the sword.
- That Woman Is Dead: Declares Asaemon to be dead after taking on the name Yaemon and leadership of the Ikeda Clan. To symbolize this she cuts her skull mask in half.
Yaemon Ikeda, Jr.
Voiced by: Isshin Chiba, David Kaye (EN)
The current head of the Ikeda Clan, which comprise a long line of executioners for the Bakufu. He serves as the Bakufus official executioner and sword-keeper, which means that he controls and distributes swords for the Bakufu, and is also responsible for testing them on the corpses of criminals.
- Achilles' Heel: The Ikeda style of swordsmanship is mainly used for the sake of quick and painless executions. While it's very effective in combat, the style has a critical weakness in that the user is left open after an attack, which can be exploited by making the user waste their attack.
- Arc Villain: Of the Shinigami Arc.
- Badass Back: Flips around the Hitotsubashi retainers with his back turned to them in his You Shall Not Pass! moment.
- Cain and Abel: The Cain to Asaemons Abel.
- Combat Pragmatist: Brings in riflemen as backup and goads Asaemon into wasting her attack on Gintoki in order to kill her when shes let her guard down, though the latter plan doesnt work as intended.
- Dissonant Serenity: Always smiling and polite, even when he's sneaking up on somebody and threatening to cut them up.
- Eyes Always Shut: Keeps his eyes closed most of the time, rarely opening them.
- Face Death with Dignity: He takes his death calmly, standing still as Nobunobu walks up to him and cuts off his head.
- Historical Domain Character: Based on the eighth and last Yamada family head who bore the Asaemon name.
- Iaijutsu Practitioner: Part of the Ikeda swordsmanship style consists of quickly drawing his sword to execute a criminal.
- Implausible Fencing Powers: Most swordsmen in the series get some improbable feats, but he and his sister Asaemon take it to another level with the special techniques of the Ikeda Clan, which allows them to cut things in a way so they either stay attached or can be easily reattached. The primary use of the technique lies in executing criminals without letting their heads fall off, allowing them to die with some semblance of dignity.
- Legacy Character: Invoked. Every head of the Ikeda Clan take on the name Yaemon.
- Off with His Head!: As the Bakufu's chief executioner, his job entails cutting off the heads of criminals. He ends up getting his own cut off by Nobunobu himself.
- Oh, Crap!: He panics when he notices just a bit too late that Asaemon has given her sword to Gintoki while he himself is open to attack.
- Passing the Torch: Hands over the name of Yaemon and leadership of his clan to Asaemon after his defeat.
- Perpetual Smiler: Never lets go of that smile on his face.
- Redemption Equals Death: Redeems himself by allowing Asaemon and the Yorozuya to escape, but it costs him his life.
- Red Eyes, Take Warning: He has red eyes in the anime. When he opens them at least.
- Villain's Dying Grace: After being defeated by Gintoki, he allows Gintoki and Asaemon to escape from the pursuing Hitotsubashi retainers by holding them back, but pays for it with his life.
- "Well Done, Son!" Guy: Desperate to prove himself worthy of the title of the clan's head, to the point where he murders several criminals ahead of time in order to master the Ikeda style of swordsmanship. His father did not approve.
- You Shall Not Pass!: Stands against the Hitotsubashi retainers to allow Gintoki and Asaemon to escape after his defeat. Nobunobu cuts off his head for it.
Yaemon Ikeda, Sr.
Voiced by: Keisuke Ishida
The previous head of the Ikeda clan, who also served as the royal sword-keeper and official executioner for the Bakufu. He adopted Asaemon and raised her along with his own son, training them both to eventually succeed him as the next Yaemon and head of the clan.
Unfortunately for the clan, it was eventually discovered that he had released several prisoners that were due for execution, having believed them to be innocents. To prevent this information from leaking out and shaming the clan, the matter was handled internally, allowing Yaemon to commit seppuku with Asaemon as his assistant.
- Badass Mustache: Had a nice mustache to go with his position.
- Berserk Button: Mistreating prisoners under his care is a grave offense in his eyes. He even drew a sword on his own son (though he didn't use it) when he found out he executed a lot of prisoners before their time simply to master the family techniques.
- Dark Is Not Evil: He was the previous royal excutioner, but treated the prisoners he had to execute with respect and allowed them to die with dignity.
- Honor Before Reason: Took responsibility for releasing prisoners whom he considered innocent and committed seppuku.
- Historical Domain Character: Based on the seventh generation Yamada Asaemon, who was notorious for executing members of the joi shishi faction during the Ansei Purge. Of interesting note, he was the one who executed Yoshida Shoin, the basis for Gintoki's master Shoyo.
- Implausible Fencing Powers: He's mentioned as a master of the Ikeda style of swordsmanship, which allows the user to cut things in a way that allows them to stay or be easily reattached. The use of the technique is intended for executing criminals without letting their heads leave their necks, allowing them to die with dignity.
- Off with His Head!: Asaemon serves as his assistant during his seppuku and cuts off his head.
- Posthumous Character: Dead by the time of the Shinigami arc, but his character is explored through flashback.
- Screw the Rules, I'm Doing What's Right!: At the end of the war, he released a number of prisoners captured by the Hitotsubashi, believing them to be innocent. One of those prisoners also happened to be Gintoki, who recalls the man with admiration.
- Seppuku: Subjects himself to honorable suicide to not bring shame on the clan.
Voiced by: Toshiyuki Morikawa (JP), Fred Henderson (EN)
The leader of the newly-established and significantly more illustrious Mimawarigumi. He comes from an elite samurai family, with the skills and training to match. He's polite and disdainful—but his personality changes completely when he uses emails, becoming sickeningly sweet instead.
At the end of his first appearance, he was shown amiably conversing and plotting with Shinsuke Takasugi, suggesting an alliance between the two. He's also backed by the Hitotsubashi faction, which is opposed to Sadasada and seeks to install Nobunobu Hitotsubashi as shogun.
- Aloof Big Brother: He calls his younger half-brother Tetsunosuke a failure right to his face and doesn't have any qualms with letting him die if the situation calls for it.
- Ambiguously Evil: Was shown having a friendly conversation and possibly plotting with Takasugi, but his actual motivations remain unknown through most of his appearances. His plan is to provoke a new rebellion against the corrupted Bakufu and Tendoshu, taking down the country with him.
- Badass Longcoat: Wears a rather awesome white longcoat as part of his uniform.
- The Captain: Of the Mimawarigumi.
- Cavalry Betrayal: Subverted in the Courtesan of a Nation Arc. While he initially makes it seem like the case when he arrives at the scene and shoots Gintoki, it's quickly revealed that he shot him with an antidote to Oboro's poison, making him genuinely part of The Cavalry.
- Cerebus Retcon: You know the gag of him sending sweet emails on his phone as a habit? Turns out it has a rather dark twist to it... His pregnant wife made him use a phone so they could communicate while she was giving birth to their child. However, after making sure the Shinsengumi succeeded in their first mission, the Naraku turned on his family, killing his wife and newborn child.
- The Chessmaster: It's heavily implied he planned and orchestrated the events that led to the former Shogun Sadasada being ousted from his position, though certain details, such as Shigeshige's attempted (but rejected) resignation, were not part of his plan.
- Combat Pragmatist: Brings a gun to a sword-fight and doesn't hesitate to use the environment to his advantage.
- The Comically Serious: Completely serious and composed at all times, even when writing his sickeningly sweet e-mails or trying to shake Nobume off the hand he held a donut in.
- Crusading Widower: The Naraku murdered his wife and newborn daughter as punishment for Isaburo secretly helping the Shinsengumi complete their first mission. Isaburo swore revenge against the corrupted Bakufu and Tendoshu, but instead of rebelling immediately, he spent years pretending to still be their loyal enforcer and waited for the right moment to turn the tables.
- Cultured Badass: Sophisticated elite asskicker.
- Cultured Warrior: A sophisticated and well-spoken fighter.
- Cynicism Catalyst: He was much less ruthless and arrogant in the past, to the point he opposed to the Naraku using children as assassins. When he foiled an assassination he found too wrong, the Naraku murdered his wife and newborn daughter. This was what made Isaburo swear to spark rebellion against the Bafuku and Tendoshu.
- Dark and Troubled Past: He had a pregnant wife who was discussing with him by phone on what to name their child... only for them both to get killed by the Naraku in retaliation for Isaburo covertly helping the Shinsengumi complete their first mission.
- Death Seeker: Since his plans involve provoking a rebellion against Nobunobu's government and the Tendoshu, he has no intentions of surviving. In fact, he tasks Nobume with killing him.
- Dragon with an Agenda: As the new Police Chief, he serves as Nobunobu's chief enforcer, but is really not loyal to him or the Tendoshu. His actual intentions are to provoke a rebellion against the Bakufu and Tendoshu.
- Enigmatic Minion: His motives and goals are only hinted at, while his actions confuse people even further.
- Exactly What I Aimed At: Shoots a charging Hijikata (who was counting on taking the hit so he could attack a vulnerable Isaburo) through his shoulder, with the bullet hitting barrels of gasoline behind him, which explodes and throws Hijikata straight in the path of Isaburo's sword.
- Good All Along: For a given value of "good". He's trying to spark a rebellion against the Bakufu and the Tendoshu, hoping to be taken out in the process while the country destroys itself.
- Go Out with a Smile: Falls to his death from a flying ship with a smile on his face after saving Nobume and his half-brother Tetsunosuke from a bunch of Naraku.
- Gun And Sword: Wields both a sword and a pistol at once to stunningly deadly effect.
- Heroic Sacrifice: He saves Nobume and his half-brother Tetsunosuke from a bunch of Naraku who were about to kill them and gets stabbed through the back for his trouble, before he falls to his death.
- High-Class Glass: As seen above, he wears a monocle befitting his elite status.
- Historical Domain Character: His historical counterpart is Sasaki Tadasaburo, the leader of the real Mimawarigumi. In a significant ironic twist, despite the real Tadasaburo and Mimawarigumi remaining loyal to the Shogunate in its dying days, Isaburo became a significant player during the subsequent fall of the Bakufu in the closing arcs of the story.
- Jerkass: He's more condescending than he's truly evil. His default attitude is very apathetic and arrogant to everyone, especially his half-brother. He's only nice in his text messages.
- Keigo: Addresses everyone politely.
- Light Is Not Good: Despite wearing purely white clothes, his intentions are morally questionable at best.
- Major Injury Underreaction: He barely reacts at all when he gets run through with a poisoned katana.
- Manipulative Bastard: He's quite good at playing everyone around him with words.
- Nerves of Steel: He never flinches from any kind of threat, at most acting with mild surprise that he's actually been stabbed.
- No Celebrities Were Harmed: Based off of the Mimawarigumi captain Sasaki Tadasaburo.
- No Good Deed Goes Unpunished: He foiled an assassination attempt from the Naraku in order to save the Shinsengumi from having to commit seppuku for the crime, as well as preventing children from being used as assassins. The Naraku got a wind of what Isaburo did and assassinated his family in retaliation.
- Parental Substitute: He took Nobume under his wing when she was a child, intending to use her skills as an assassin to further his own plans and eventually order her to kill him once he succeeded in starting a rebellion. Despite the way their relationship started, Nobume ended up becoming the closest thing to family Isaburo had left. In his final thoughts, Isaburo acknowledges Nobume as the daughter he always wished he had.
- The Proud Elite: He is the heir of the elite Sasaki family, with the skills to match and he will proudly remind you of the latter as many times as possible.
- Revolvers Are Just Better: Uses one in the manga. The anime version has him use a modern pistol instead, though he did use a revolver when he shot Gintoki with an antidote.
- Secret Secret-Keeper: He had long figured out that Nobume wasn't the real murderer of his wife and child. However, he let her assume the blame so she wouldn't hesitate to kill him once his revenge was done.
- So Proud of You: His final thoughts are something along the lines of this, about Nobume. Isaburo was happy that Nobume grew into a girl who has many friends, can get along with everyone, is kind-hearted and strong-willed; everything Isaburo wanted for his daughter.
- Stalker Without a Crush: He has a habit of sending text messages every few seconds to the point of annoying the receiver until he gets an answer. Turns out there's a tragic reason behind this. He and his wife texted each other as they waited for the birth of their firstborn. One day, she suddenly stopped replying his messages and when he went to search for her, Isaburo found she had been murdered by the Naraku.
- The Stoic: He's usually stone-cold and composed.
- Sugar-and-Ice Personality: Is usually quite cold but he's much nicer when he's writing e-mails. A bit too nice.
- Taking the Bullet: Pushes away Nobume and Tetsunosuke and shields them when a bunch of Naraku attack from behind.
Voiced by: Aya Hirano (JP), Chiara Zanni (EN)
The Vice-Commander of the Mimawarigumi. A cold and highly efficient assassin with a surprising fondness for donuts.
It is later revealed that she used to work alongside Oboro in the Naraku and was known as Mukuro, with a tattoo on her neck to show for it. However, she has made it clear that she has no intention of joining forces with him and remains loyal to Isaburo.
- The Atoner: Hates herself for all the deaths she has caused and failing to stop the assassination of Isaburo's family. To make up for it, she joins in his cause, but finds herself unwilling to follow through on his final order to kill him. She ultimately decides to atone by choosing her own path instead of blindly following someone's orders.
- Ax-Crazy: Played for Laughs. Whenever there's a problem you can expect her to suggest cutting it up.
- Badass Longcoat: Wears a white longcoat as part of her uniform.
- Child Soldiers: Served as a highly skilled assassin in the Naraku even as a little child.
- Contralto of Danger: Aya Hirano gives Nobume a very deep-sounding voice to emphasize the deadly assassin she is.
- Cool Big Sis: She acts like a big sister for Soyo. They even share a bed!
- Cry Cute: In the Farewell, Shinsengumi arc, the peak of her defrosting occurs when she sheds tears for Isaburo.
- Dark Action Girl: While her motives are unclear, she's still a ruthless assassin that won't hesitate to cut you up. Turns into a normal Action Girl after Isaburo's death.
- Defector from Decadence: She deserted the Naraku after Shoyo's teachings and the assassination of Isaburo's family made her realize just how wrong it was to work for people that allow corruption to happen.
- Defrosting Ice Queen: While she starts out cold and emotionless, she warms up slowly to Soyo and the Yorozuya. Her true defrosting begins during the battle at Kokujou Island, where her refusal to kill Isaburo leads her to acting more emotionally and independently. It culminates in her tearfully bidding farewell to Isaburo, her eyes now shining bright with life.
- Distaff Counterpart: She's basically a female Sougo. Both are sadistic Heroic Comedic Sociopaths who are closer to being a Psycho for Hire instead of a police officer. The one thing that keeps them from being mere assassins is their Undying Loyalty for their respective commanders. Nobume herself even points out Sougo has the same murderer's eyes as her when they first meet.
- The Dragon: To Isaburo as the vice-commander of the Mimawarigumi.
- Dressing as the Enemy: Along with Gintoki and Tsukuyo, she disguises herself as a member of the Naraku to sneak aboard Sadasada's escape vessel and destroy the ship's core.
- Dual Wielding: Has a tanto sheathed in the bottom end of her sword's sheath which she occasionally uses in conjunction with her nodachi.
- Emotionless Girl: Never shows any emotion. Except when donuts are involved.
- Empty Eyes: Reflecting her cold nature and profession as an assassin, her eyes are lifeless and without light. After Isaburo's death, they begin reflecting light and are filled with life.
- Hime Cut: Being set around the time of the Bakumatsu, her hairstyle makes at least some sense. It looks right for the trope and she fits the "loyal" and "elegant" character traits.
- Historical Gender Flip: The inspiration of her character's name is Imai Noburo, a male former member of the Mimawarigumi.
- Iaijutsu Practitioner: Her preferred style is quickly drawing and then sheathing her nodachi.
- Lady of War: Swings her sword with a deadly lady-like grace.
- Lonely Together: This is what originally motivated her to stay with Isaburo. Isaburo took her in to use her for his revenge after his wife and daughter were murdered. Nobume became his subordinate to atone for failing to save his family, but she also didn't want to be alone and wished to keep Isaburo company after he lost everything.
- Meaningful Name:
- The name given to her by Isaburo, Nobume, literally means "girl of faith". That was the name Isaburo intended to give to his deceased daughter. Since Isaburo and his wife wished their child to grow up into a good person with many qualities, he came up with Nobume to symbolize his faith that his daughter would become everything her parents hoped. Before he dies, Isaburo feels glad that the girl he named Nobume is everything he wished his daughter would be.
- Her original name, Mukuro, means "corpse". It was befitting given her upbringing as a child assassin and reputation as the "bastard child of a Shinigami" because of her exceptional skill at murder.
- Meaningful Rename: She was called Mukuro, meaning "corpse", when she was a child assassin serving the Naraku. After she became the vice commander of the Mimawarigumi, Isaburo renamed her Nobume Imai, saying her original name was too ominous for a police officer. Turns out Nobume was the name Isaburo wanted for his daughter.
- My Greatest Failure: She failed to protect Isaburo's wife and newborn daughter from the Naraku and let Isaburo live with that grief. Ever since, she has loyally served under Isaburo to at least make sure he isn't alone.
- Not So Above It All: While she will keep up her stoic composition, she's one of the few people to always join Gintoki during his antics.
- Not So Stoic: Mostly when donuts are involved, but she's not incapable of crying. Especially after Isaburo falls to his death after saving her and Tetsunosuke.
- One-Handed Zweihänder: She wields a nodachi, a two-handed weapon, in one hand due to being a Iaijutsu Practitioner, but also because she sometimes wields a tanto in the other hand.
- Red Eyes, Take Warning: She's stone-cold assassin with red eyes, be warned.
- Rei Ayanami Expy: A blue-haired, red-eyed girl with an eerily emotionless behavior (unless there's donuts around) and a monotone voice. She displays Undying Loyalty to her morally ambiguous boss who is the closest thing to a father she has. Said boss also took her in and renamed her to be a Replacement Goldfish for his deceased daughter. It's eventually revealed she's not as cold-hearted as she seemed at first and becomes much more emotional over time. When she was a child, she had a bob haircut like Rei just to drive the point across.
- Replacement Goldfish: A mundane and positive example. Isaburo appears to have taken her in as a replacement for his dead newborn daughter, naming her what he'd intended to call his own daughter: Nobume.
- Silent Scapegoat: She pretended to be the murderer of Isaburo's family in front of him. The truth is that Nobume had tried to save them from the real assassins and since she failed, she thought she should let Isaburo hate her. However, Isaburo saw right through it and just played along until shortly before his death.
- The Stoic: She's cold and composed at virtually all times. Well, except for when it comes to donuts.
- Suddenly SHOUTING!: Her demeanors are mostly stoic and cold and she rarely ever raised her voice... until that one time Sougo mocked her by eating her Trademark Favorite Food while she couldn't, because she's behind the bars. Played for Laughs of course.GAAAAAHHHHH!!! GIMME MY PON-DE-RING!!! (pulls Sougo's leg while Kagura did the same to the other leg, inflicting something in you-know-where)
- Sugar-and-Ice Personality: The first impression you get of Nobume is that of an emotionless, cold-hearted and ruthless killer who only cares about donuts. Eventually, Nobume is proved to be a human being very much capable of love and compassion through her strong bond with Isaburo.
- Trademark Favorite Food: Her favourite food is donuts, which Sasaki uses to bribe her.
- Tyke-Bomb: She was raised and trained by the Naraku to be an assassin who would follow their orders without question. However, she ended up defecting to work for Isaburo after seeing the evil of their ways thanks to Shoyo.
- Undying Loyalty: Shown to be very loyal towards Isaburo, trusting in his survival and stating to Oboro she only works with Takasugi because he is.
- Voice Changeling: She can imitate the voices of other people to perfection, as seen when she speaks with the shogun's voice.
- Who Wears Short Shorts?: Although hers are hidden by her long white coat.
- Wild Card: Just like Isaburo, her motives are pretty unclear. Especially since we know that she used to work with Oboro.
- You Gotta Have Blue Hair: Dark blue at that.
- Zettai Ryouiki: She wears a pair of shorts and thigh-high socks.
Voiced by: Kazuhiko Inoue (JP), Mark Oliver (EN)
The leader of the Naraku, a secret assassination squad employed directly under Sadasada Tokugawa, but is actually serving the Tendoshu.
He was the one responsible for Kansei Purge which eradicated most of Anti-Foreigner Faction of the past including the falsely accused Shoyo Yoshida.
- Acquired Poison Immunity: He's immune to the poison he coats his needles in.
- Animal Motifs: Crows, specifically the three-legged crow Yatagarasu which is considered a symbol of the will of heaven or divine intervention in Japanese Mythology.
- Arch-Enemy: To Gintoki, but less so than Takasugi.
- An Arm and a Leg: Kondo cuts off his left arm from behind while Hijikata attacks from the front. He shows up alive later with a new arm.
- Artificial Limbs: After Kondo cuts off his left arm he replaces it with a mechanical arm.
- Bare-Fisted Monk: Still a quite capable fighter without weapons, mixing martial arts with ki attacks.
- Blood from the Mouth: Starts coughing up blood after turning up alive from being cut up by Kondo and Hijikata. The immortal blood that allows him to survive fatal injuries is beginning to take its toll on his body after dying so many times.
- Combat Pragmatist: Utilizes poisoned weapons and paralyzes his opponents to gain an advantage in a fight.
- The Dragon: He works as Sadasada's right hand man.
- Dragon with an Agenda: While he seemingly serves Sadasada, his true loyalty is to the Tendoshu, specifically Utsuro.
- Driven by Envy: It's implied that Oboro revealed Shoyo's location to the Naraku and had him arrested because he grew jealous of his new students enjoying a peaceful life with their teacher while Oboro had to leave Shoyo to stop the Naraku pursuit.
- Evil vs. Evil: Due to his allegiance towards the Tendoshu, he also considers Takasugi an enemy.
- Eye Scream: Karmically, Takasugi stabs out his left eye while he's busy fighting Gintoki as payback for stabbing out Takasugi's eye in the past.
- Face Palm Of Doom: Grabs Gintoki's face while he's already downed and blasts him point-blank with a Ki Manipulation.
- The Fatalist: Is of the belief that those who have been dealt a bad hand by fate should accept it, as they can't change anything and any attempt will only result in further loss. It's part of the reason he hates Gintoki so much, as he sees him as refusing to learn from the losses he's suffered and continuing to oppose the people in charge who were responsible. This is the result of him failing to live up to Utsuro's teachings who was trying to atone. Then he was the one who captured his former teacher and had him executed to come back as Utsuro.
- Fond Memories That Could Have Been: He spends his final moments imagining what his life could have been if instead of serving the Naraku, he had stayed with Shoyo and became friends with his fellow students.
- Good Scars, Evil Scars: Has a long scar across his face which he got the first time he was killed as a kid.
- Hidden Weapons: He's got a sword hidden inside his staff, though Gintoki breaks it immediately. He also has a lot of needles hidden inside the straw hat he wears.
- Impaled with Extreme Prejudice: With Gintoki's wooden sword. However, he survives thanks to the intervention of the Tendoshu.
- I Owe You My Life: Fiercely devoted to Utsuro for saving him as a kid by giving him some of his immortal blood.
- Ki Manipulation: Able to produce short range ki blasts from the palm of his hands.
- Knight Templar: Any act of defiance towards the Tendoshu's rule is a crime against the heavens in his eyes.
- Laser-Guided Karma: Twice from the same person:
- He stabbed out Takasugi's left eye with a thrown dagger to stop him from charging in after Shoyo's execution. Takasugi later pays back the favor stabbing out his left eye while he's busy fighting Gintoki.
- Ends up being defeated and fatally struck down once and for all by Shoyo's pupil Takasugi.
- Light Is Not Good: Dresses in white robes and claims to speak for the heavens, but his intentions are by no means noble.
- Not Quite Dead: The Tendoshu retrieve and patch him up after Gintoki had presumably killed him. Later again after both Kondo and Hijikata cuts him up, he shows up at a meeting with Harusame.
- There's a very good explanation for it: Utsuro gave him some of his immortal blood when he was dying, allowing him to live through fatal injuries, however it's taking its toll on his body.
- After being defeated by Takasugi, he is finally dead for good.
- Ninja: While he looks like more of a warrior monk, his role as an assassin and the skills he wield puts him in the role of a ninja.
- Oh, Crap!: When he notices that he's about to fall down and be impaled upon a piece of Gintoki's broken wooden sword.
- The Paralyzer: In addition to being poisoned, the needles will severely immobilize his opponents when they strike a Pressure Point.
- Perpetual Frowner: Rarely ever seen cracking a smile.
- Poisoned Weapons: His needles are coated in a deadly poison that will immobilize and kill its target.
- Power Palms: Utilizes palm strikes against his opponents in hand-to-hand combat, sometimes combined with a Ki Manipulation.
- Pressure Point: Attacks enemy pressure points with his needles in order to immobilize and damage his opponents, though he is quite capable of hitting them personally in close quarters.
- A Pupil of Mine Until He Turned to Evil: He was Utsuro's first disciple who was atoning for his behavior until he went against his teachings and became a full-fledged assassin in the Naraku, to the point of capturing him and having him executed.
- Staff of Authority: The Naraku wield khakkhara (Buddhist monk staves) with hidden swords inside as their main weapon.
- Stealth Hi/Bye: In his talks with Nobume, he's made a habit of disappearing when she looks for him, leaving only raven feathers behind.
- Sword and Fist: Fights with both weapons and martial arts at the same time.
- Sword Cane: The khakkhara the Naraku wield are essentially this, featuing hidden blades inside of them.
- Villainous Breakdown: Really loses his cool in the final stages of his fight with Gintoki, though he recovers after he is revealed to be alive.
- Warrior Monk: He's dressed like a monk and addressed as a messenger of heaven.
- White Hair, Black Heart: Unlike Gintoki, Oboro is a definite villain.
- Wrecked Weapon: Gintoki breaks his first sword with his teeth. Later on in the fight as well, he breaks Oboro's second sword with his own wooden sword.
Voiced by: Kōichi Yamadera (JP), Simon Hayama (EN)
First leader of the Naraku, who rose to become one of the Tendoshu.
- Agony of the Feet: Nobume manages to stab him through his right foot to trap him in place, though he barely reacts to it.
- Animal Motif: Like Oboro, a crow. He referred to himself as "the yatagarasu", the three legged crow associated with Heaven's will in Japanese Mythology, and also wears a cape of raven feathers.
- All-Encompassing Mantle: That black cloak of his covers his entire body.
- Back from the Dead: He has been killed multiple times, but always comes back from the dead. This includes coming back as Utsuro after Shoyo was killed.
- Badass Cape: His black cloak is adorned with raven feathers.
- Bare-Handed Blade Block: Grabs Nobume's blade with only three fingers, then smacks the hilt into her open wound with it.
- Being Tortured Makes You Evil: One of previous Utsuro's lives endured endless torture as a kid as he wouldn't die.
- Big Bad: Appears in the Farewell Shinsengumi arc and takes over the role of the main villain from Takasugi for the rest of the series.
- Big Bad Duumvirate: As one of the Tendoshu, he is part of the council that truly controls the country and vies with Takasugi for the Big Bad position.
- Black Cloak: Covered completely from the neck down in a black cloak, which gives him both an air of mystery and intimidation.
- Black Swords Are Better: Wields a black katana with a manji-shaped guard. Remind you of anything?
- Blood Knight: He mentions being bored of only having to deal with the other members of the Tendoshu and regards his presence on the battlefield as him finally getting some fun for himself.
- Board to Death:
- Meets with the Elders of the Harusame only to forcibly take control of the Harusame and then kill all the Elders.
- He later meets with the rest of the Tendoshu, revealing his plans to blow up the Altanas on various planets, leading to the Altana Liberation Army coming to Earth to get revenge, before he cuts all of the Tendoshu into pieces off-screen.
- Came Back Wrong: After Shoyo was killed, his body was burned on a pyre, only for him to rise up again alive with his head attached and a changed personality.
- Charles Atlas Superpower: Doesn't appear to be a Yato, but is able to block a kick from Kagura and toss her around like a ragdoll.
- Complete Immortality: Thanks to the Altana that mutated in his body, he's immortal.
- Cool Mask: Wears an intimidating tengu mask to cover his face.
- Cool Sword: Completely black sword with a guard in the shape of a manji? Awesome!
- Darth Vader Clone: He dresses in all black, complete with an identity-concealing Cool Mask, the Tendoshu's trademark Nice Hat, and a raven-feathered Badass Cape. He even happens to be Shoyo himself, who was Gintoki's master and father figure.
- Death of Personality: When Nobume said that Gintoki wasn't the one who killed Shoyo, she was right. Shoyo was actually killed by his darker self Utsuro by the time Gintoki was forced to execute him and ends up taking over. Now after he's finally defeated, Shoyo comes back but the remnants of the Naraku are planning to bring him back as Utsuro like last time.
- Death Seeker: Is hoping to find a way to finally die.
- Dissonant Serenity: Has a cheerful smile on his face when he tries to cut off Gintoki's head.
- Dramatic Unmask: Gintoki breaks his mask in their fight, revealing him to look just like Shoyo. Gintoki is stunned for long enough that Utsuro almost cuts off his head.
- Evil Counterpart: Like Oboro to Gin — in both power, looks and demeanor, he is designed to be an evil Shoyo Yoshida. In fact, Utsuro and Shoyo are one and the same. His time as Shoyo was a brief moment in his 500-year long life, and he returned as Utsuro after getting killed and then resurrected.
- Flash Step: He is fast enough to disappear and then appear behind Nobume to attack her.
- From a Single Cell: He can rapidly regenerate himself from any part of his body.
- Hat of Authority: A member of the Tendoshu and wears the same style of straw hat as the rest of them.
- Healing Factor: He finishes healing a deep cut through his shoulder before he can finish a sentence. The reason is because of the Altana, also known as the Dragon's Vein, which is the lifeforce of the planet. For some reason it heals his wounds and brings him back from the dead along with a new head.
- Taken to extreme levels when he is thought to be defeated by Umibouzu, using an Altana crystal from his wife's planet to negate his healing ability and crush his heart. Only he comes back in a new body, thanks to pouring his large amount of Altana in his severed right arm! This apparently takes a large amount of the Altana's power, so he is required to go back to Earth to recharge.
- Implacable Man: No matter what the good guys do to try and stop him, Utsuro will keep coming back at them.
- Meaningful Name: "Utsuro" means "hollow", as in "empty". His latest incarnation feels empty because he doesn't know what "death" would mean to him.
- Me's a Crowd: Utsuro's will lives on in the bodies of the Tendoshu who he gave blood to as Takasugi discovered, turning them into basically clones of him complete with his fighting skills to fend off the heroes while his original body is regrowing the heart so he can be fully resurrected.
- Never Given a Name: Utsuro is actually just a pseudonym he took along the way. He has been alive for 500 years, and his latest incarnation is a Split-Personality Merge. As a result, he doesn't remember if he ever received a name in his earlier life.
- Nice Hat: Wears the usual large straw hat like the rest of the Tendoshu and Naraku.
- Omnicidal Maniac: Oh, big time since he wants to literally destroy the world itself to just to try to end his life.
- Perpetual Smiler: Keeps smiling without interruption as soon as the mask comes off. Something he shares with Shoyo himself, since his latest personality at the end merged with him and his all past selves.
- Power Palms: Like Oboro, he also uses palm strikes against his opponents in hand-to-hand combat.
- Psychotic Smirk: Flashes an excited and sadistic smile while ordering the Harusame fleet to fire upon and kill the Elders of the Harusame.
- Really 700 Years Old: According to Nobume, he's more than 500 years old. That is because Utsuro is actually immortal.
- Reincarnation: After his final battle, he comes back as a rapidly aging child.
- Split Personality: Endless torture made him split into multiple personalities, the latest Utsuro is the result of a bitter Split-Personality Merge.
- Staff of Authority: Carries a khakkhara like the rest of the Naraku, but with a more ornate design.
- Suicidal Cosmic Temper Tantrum: Utsuro won't be satisfied with just ending his own immortal life. He wants to destroy the planet Earth and all life in it because of all the suffering it has caused him.
- Sword and Fist: Mixes in martial arts with his sword to deadly effect.
- Walking Spoiler: His appearance and true identity is a major twist with huge ramifications for the rest of the series.
- Warrior Monk: As the head of the Naraku, it goes without saying he's dressed as a monk and deadly as a warrior.
- Woobie, Destroyer of Worlds: It's hard to not feel sorry for the guy, but still get angry at him for the pain he has put others through.
The last of the Three Feathers of the Naraku, the top three members of the group.
- An Arm and a Leg: Gintoki cuts off his right arm with an Altana sword, then stabs him with his own wrist-mounted blade for good measure.
- Blade Below the Shoulder: Wields a pair of short retractable blades attached to his armguards.
- Blood from the Mouth: Starts coughing up blood as he gets affected by Gintoki's Altana sword.
- The Dragon: Takes up this role to Utsuro following Oboro's death.
- Healing Factor: Utsuro's blood grants him limited healing ability and allows him to survive fatal wounds.
- Informed Ability: He is identified as one of the Three Feathers of the Naraku when he appears, implying he is on the same level as Oboro and Nobume, but he immediately gets wrecked by Gintoki and would have died from getting stabbed with several swords if not for Utsuro's immortal blood. While he does put up a much better fight against Gintoki afterwards, the damage to his reputation as a fighter is already done.
- Oh, Crap!: While he doesn't say anything, his eyes are wide open in shock when Gintoki manages to stab his wooden sword through both his arms and into his mouth.
- The Quiet One: He rarely ever says anything, his only words being a warning to Utsuro about Gintoki wielding an Altana sword.