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Voiced by: Yuki OnoAlso 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 appearence. It's a record even for 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/Go Out with a Smile: Dies peacefully and smiling with his head on his unknowing sister's lap.
- Historical-Domain Character: His historical counterpart is Tokugawa Iemochi, who was Shogun during the Bakumatsu period.
- 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.
- Our Shoguns Are Different
- 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's secretly crying on the inside.
- Teeny Weenie: Mentioned in his first episode after he strips off all his clothes.
- 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 HirohashiShigeshige'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.
- Cloudcuckoolander: Sees no problem in sneaking into a prison for sleepover.
- Cute Is Evil: She isn't really evil, but she enjoys the suffering of others if it makes herself look good.
- Everything's Better with Princesses: As a member of the ruling Tokugawa Clan, she's considered a princess.
- Forehead of Doom: Has a rather prominent forehead.
- I Just Want to Have Friends: 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.
- Sadist: According to both Kagura and Shinpachi. Unlike Okita is she more of a psychological sadist rather than a cruel fighter. And seemingly enjoys watching others in pain rather than directly causing it. Even if it's her own best friend, which Kagura fell victim to.
- Spoiled Sweet: Despite her upbringing she's a sweet girl.
Voiced by: Takaya HashiShigeshige'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 made his actual appearance in the Courtesan of a Nation arc.
- 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's Soyo's and Shigeshige's uncle, but has little to no good intentions to do with them.
- Fat Bastard: He's really let himself go in his old age.
- 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, accidently 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: At least he thought so...
- 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 NamikawaMember 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.
- 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 Liberation Army wanting to use the bathroom thanks to Kagura spiking his food with excessive seasonings as her way of payback.
- 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.
- Heel–Face 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 becoming Shogun, he ends up getting knocked out by Gintoki for attempting to kill Tae. After the Farewell Shinsengumi Arc, he loses both the Shinsengumi and Miwarigumi as police forces and other police forces end up defecting. Then when he attempts to stop Gintoki and others from leaving Earth, they immediately ambush and capture him, and afterwards humiliate him in front of his retainers by Gintoki, Katsura, and Sakamoto. After he orders all retainers to kill themselves for failing to protect him, he gets knocked out in one punch by Bansai which broke off his two front teeth and 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 supported Shigeshige instead of him.
- Jerkass: Has little regard for anybody, mocking people and belittling them as he sees fit. He's also quite the sadist, taking pleasure in slowly cutting into someone's neck with a sword.
- 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 believes the country to be corrupt and beyond repair, and has similar intentions of destroying it. However, his vision seems to entail rebuilding the country in his own image. 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 pleasure.
- Only Six Faces: Subverted. With him one can see that Sorachi's art has really evolved as his face actually looks similar to the historical person's as seen here◊.
- 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.
- 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 intends to completely destroy the country, but only so that he can rebuild it into a stronger and better nation. 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 Yaemon’s head after he loses to Gintoki and helps him and Asaemon to escape.
- Attempted this again with all of his remaining forces for failing to protect him until 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 Grandpa: He's pretty fit for a man his age, going up against an entire building filled with terrorists to save his daughter.
- 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.
- 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.
- 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.
- 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: 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 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's 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.
Yaemon Ikeda, Jr.
Yaemon Ikeda, Jr.
Voiced by: Isshin ChibaThe current head of the Ikeda Clan, which comprise a long line of executioners for the Bakufu. He serves as the Bakufu’s 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 Asaemon’s Abel.
- Combat Pragmatist: Brings in riflemen as backup and goads Asaemon into wasting her attack on Gintoki in order to kill her when she’s let her guard down, though the latter plan doesn’t 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.
- 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!: When he notices 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.
- "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.
Yaemon Ikeda, Sr.
Voiced by: Keisuke IshidaThe 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.
- 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 MorikawaThe 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.
- 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 against 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.
- Cultured Badass: Sophisticated elite asskicker.
- Cultured Warrior: A sophisticated and well-spoken fighter.
- 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.
- Even Evil Has Loved Ones: 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. He then appears to have taken Mukuro in as a replacement for his daughter, naming her what he'd intended to call his own daughter: Nobume.
- 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.
- 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.
- Man in White: Complete with having rather shady motivations.
- 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.
- The Proud Elite: He's 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.
- 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.
- Waistcoat of Style: Under his uniform.
- Well-Intentioned Extremist: What he turns out to be.
- Wild Card: A rather grey character since it's never really clear whether he's an antagonist or just neutral.
Voiced by: Aya HiranoThe 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.
- Cool Big Sis: She acts like a big sister for Soyo. They even share a bed!
- 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.
- 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: To Sougo.
- 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.
- 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.
- Iaijutsu Practitioner: Her preferred style is quickly drawing and then sheathing her nodachi.
- Ice Queen: Except when donuts are involved.
- Lady of War: Swings her sword with a deadly lady-like grace.
- 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.
- The Stoic: She's cold and composed at virtually all times. Well, except for when it comes to donuts.
- Sweet Tooth: Her favourite food is donuts, which Sasaki uses to bribe her.
- That Man Is Dead: Nobume Imai is a pseudonym. Oboro reveals her former name was Mukuro. Whether or not this was also a pseudonym is unknown as of now. In Chapter 539, it turns out that Nobume is the name Isaburo was about to give to his newborn dead child.
- Trademark Favorite Food: Donuts, as mentioned above.
- 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.
- 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.
- Woman in White: Well, white clothes are part of the Mimawarigumi and she's fighting alongside people with rather shady motives.
- You Gotta Have Blue Hair: Dark blue at that.
- Zettai Ryouiki: Grade A.
Voiced by: Kazuhiko InoueThe 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.
- 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.
- 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.
- 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.
- Arch-Enemy: To Gintoki, but less so than Takasugi.
- 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.
- Evil Versus 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 Attack.
- 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.
- 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 Attacks: 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 of all people.
- Light is Not Good: Dresses in white robes and claims to speak for the heavens, but his intentions are by no means noble.
- Man in White: His robes are white and his intentions are anything but benevolent.
- 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's likely dead for good once he finishes explaining about Utsuro to Takasugi
- 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.
- Older Than They Look: Utsuro's blood makes him age much slower.
- The Paralyzer: In addition to being poisoned, the needles will severely immobilize his opponents when they strike a Pressure Point.
- Perpetual Frowner: Never seen cracking a smile.
- He cracked a smile in chapter 542 when Gin broke his staff
- Poisoned Weapons: His needles are coated in a deadly poison that will kill its target.
- Power Palms: Utilizes palm strikes against his opponents in hand-to-hand combat, sometimes combined with a Ki Attack.
- 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.
- 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: Koichi YamaderaFirst leader of the Naraku, who rose to become one of the Tendoshu.
- The Ageless: He is referred to as such, thanks to the Altana that mutated in his body, making him immortal.
- 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 them all up 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.
- 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.
- 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.
- 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 was thought to be defeated by Umibouzu who used the Altana crystal from his wife's planet to cease his ability and crush his heart. Only he came back... in a new body thanks to pouring his large amount of Altana in his severed right arm! Though he admits that it took a large amount of it so he is going back to Earth to recharge.
- Meaningful Name: "Utsuro" means "hollow", as in "empty". His latest incarnation feels empty because he doesn't know what "death" would mean to him.
- The Nameless: 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.
- 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.
- 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.
- Blade Below the Shoulder: Wields a pair of short retractable blades attached to his armguards.
- 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 in the back with several swords if not for Utsuro's immortal blood.
- 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 Voiceless: He has not spoken a single word so far.