Takasugi Shinsuke (高杉 晋助, Takasugi Shinsuke) is the leader of the Kiheitai, an extremist group which he formed during the Joui Wars. The Kiheitai is a Joui faction bent on causing world destruction. He can be considered a former villain of the series, being originally meant to be the main antagonist of the series due to his first appearance until being considered as an anti-villain of the series until the end of the Shogun Assassination Arc.
According to the moderate Joui faction led by Katsura, the Kiheitai accumulates military firearms through shady arms dealing so that they can become a powerful military organisation. Contrary to Katsura, who wants to find a better solution and a way to save the world, Takasugi only wants to destroy, specifically taking down the Bakufu and targeting Sakata Gintoki due to personal grudges. He will go to any lengths to see his world destruction through, even conspiring with the Harusame. He fought alongside Sakata Gintoki, Katsura Kotarou and Sakamoto Tatsuma in the Joui wars.
Takasugi grew up very recklessly, matching his personality even today. He was prone to challenging others and swiftly defeating them, and he drifted and defeated many groups of children until one day he was "rescued" by Gintoki and Yoshida Shouyou, a samurai who had begun teaching for free in the village Takasugi and Katsura lived in. Curious about their strength at the poor school, Takasugi challenged the students there as well to kendo, only to lose to Gintoki. After the first match, Shouyou bandaged Takasugi's wounds and encouraged him to get stronger, telling him that with his strength he can become as great as a samurai as he desires and how he was looking forward to seeing his path.
Learning that their child was hanging around the school, his parents begun to threaten disowning him, but Takasugi disregarded them. He realized he was weak, mentally and physically, and he begun challenging Gin to constant battles, often to a point where his old wounds hadn't even healed before the next match. He grew to desire becoming a stronger samurai than Gintoki and finally won a match, which at that point it was finally pointed out to him that he begun visiting so often that he may as well have become a student; one could say he did the following day, as Gintoki himself told Takasugi to make up for all the loses he had by dropping by again and fighting.
Over the course of their life, Takasugi and Gintoki fought 492 times (prior to chapter 518). It's unknown if these numbers are from just their childhood or if they sparred during the Joui wars.
By the time the Kansei Purge occurred, Takasugi and Katsura abandoned their previous schools to learn at Shouyou's. Over the course of this time, Takasugi obviously became attached to Shouyou, to a point where his grudge against the Bakufu runs so deeply rooted in his attachment the grief never left. He wasn't present, it seems, when Shouyou was arrested, but he did make a request to Gin on the battlefield to keep their teacher alive. However, he was present when Shouyou was executed alongside Katsura and Gin, and this event scarred him for life: not only did he see his own comrade Gin execute Shouyou, but Takasugi comments the last thing his left eye ever saw was Gintoki's tears after being forced to execute their own sensei.
Takasugi, Gintoki and Katsura were classmates under the same tutelage of Shouyou until their teacher's capture, but Takasugi has always regarded himself as a student of Shouyou's, the bond being much more outward and personal than Katsura's or Gin's thoughts. After the Kansei Purge event Katsura , Gintoki and Takasugi would rise up as the last warriors of the Joui Patriots because the government killed Yoshida Shouyou.
He would later become comrades with Sakamoto Tatsuma in the Joui War. He would create Kiheitai group during the war.
Takasugi has short, black hair with dark-purple highlights, often appearing pure dark purple in some shots. His left eye is bandaged as it was caused by Oboro during Joui war and after Shouyou's death, and he is usually seen wearing a yukata with a design dependent on the medium and occasionally a haori jacket to go with. He is usually seen smoking a thin pipe called kiseru (キセル), a pipe commonly used to smoke tobacco (and also showed high social status), when gazing from his ship's windows. He has also been seen playing the shamisen and wearing a sedge hat.
In the Class 3-Z universe, Takasugi wears the standard school uniform but has unbuttoned it to reveal a crimson red shirt underneath. He wears a more standard, medical eye patch and he doesn't seem to smoke in this universe.
As a samurai in the Joui war, he wore a low-collared black vest under a long coat lined with violet cloth and patterned with gold-colored lines. He wore with it black pants, black boots (similar to the ones Gin wears today) and a white obi. Like his companions he also adorns his head with a long strip of white ribbon, which may actually be what his bandage is made out of. Turning this time his hair is a lot more smoother and well-kept.
As a child, he wears a light green kimono with a diamond pattern trimming the edge. Over it, he wears a violet or crimson haori with no design.
Takasugi Shinsuke's Gallery
A ruthless man, Takasugi is defined by his tenacity towards destroying the world. A very charismatic individual, all of his soldiers willingly trust and assist him in his desire. However, it's very clear that he is not exactly the most stable person around and he openly admits it: often comparing himself to a beast, Takasugi is driven by anger and guilt that runs through every action he does. He rejects the change of the world and refuses to see anything but the path of total destruction, willing to kill his subordinates if they defy him or get in his way even by accident. His cold nature is widely feared by those who respect him and it's best not to turn on him.
Most of his bitterness originates from the loss of his mentor Yoshida Shouyou, as Takasugi wants to destroy the world that took away his teacher. According to Imai Nobume, Takasugi seeks to destroy what Shouyou left behind, but this is hypocritical as he still cherishes his memories from back then. The idea to take revenge for his teacher's death clouds his mind and it's what drives him to be antagonistic towards Gin and the Bakufu, for it was both the Kansei Purge and the Shiroyasha that took his dear teacher away. If it were not for the loss of his teacher, Takasugi likely never would've gone down this path.
There's a lot of hatred towards Gin, again going back to him executing Shouyou. When given the chance, the two will clash, but Gin feels like he should be the one to drag Takasugi back onto the path of peace. However, be it due to good memories or simply not having anything to hate, Takasugi seems to (barely) get along with Katsura: prior to the Benizakura arc, communicating with him while passing by and even chatting with him idly while watching a battle. However, he does have enough hatred in him to offer up both Katsura and Gintoki's heads to the Harusame Space Pirates in exchange for their co-operation in his world-destruction plans. It's unknown how he gets along with Sakamoto, but it might be either a neutral feeling (as the two were only comrades) or contempt.
Generally, though, Takasugi is quiet and more of a listener than a speaker. Like some other antagonists, Takasugi tends to appear randomly, but unlike others it's usually cameos or the like. He rarely ever takes action himself, using caution and tricks to his benefit and often being uncannily apathetic about things. He appears to be avidly watching those around him and he was quite aware of Itou Kamotarou's desire to have friends, Okada Nizou's desire of destruction, and being very receptive to the opinions of others since most of his men were recruited with similar ideologies in mind.
However, Takasugi has a peculiar tendency on humoring people, suggested by Gin or up front, despite his otherwise threatening persona. For instance, despite his antagonism towards Gin, Gin himself believed he would be one of the few to send a geniune New Year's card in chapter 294, wishing a Happy New Year and making note that he will "destroy everything this year as well", written in a style like a threat. He also dropped by and humored the jailed and broken Kada twice, guessing at "Odds and Evens", and even slipping up and calling Admiral Abou "Admiral Aho (Stupid)" like everyone else during the events of Lessons 310 and 311. It was also easy for Gin, Katsura, and Sakamoto to believe he wrote them letters about Yakult that were ridiculous enough for them to question his leadership. Furthermore, and the truth of this may be slim, Henpeita said he once ordered for the Kiheitai a large amount of Yakult and shirako because he couldn't show up for the New Year's party.
As a child, Takasugi was largely stubborn and desiring strength, something that can still somewhat be seen. He constantly sparred with Gin even when heavily wounded, battling day after day until he won and then continuing on after Gin's own suggestion. In the Joui army days, although he seemed largely concerned about Shouyou and rescuing him, he was always childish with Gin and often fought with him then, largely over petty things like choosing geisha or playing kick the can.
In the 3-Z Universe, his taste for destruction is heavily downplayed, turning into a simple case of absolute defiance. He's still quiet and commanding of his gang, but he's been seen balancing on his chair with his feet kicked up and onto his desk (see picture). He also refused to become the lead singer of Bansai's band due to "attending abacus class", despite the fact he just returned from an excessively long suspension and tending to show no interest in class.
Since the Reunion arc, he has been known for having an affection for Yakult. Although it was only mentioned in a passing set of jokes, it has made a large impact as prior to it: Takasugi lacked any kind of "features" (catchphrase, favorite food, obsession, running gag, or so on) like the other characters, so when given the chance, it became quite popular.
Strength & Abilities
Master Swordsmanship: He's an excellent swordsman, being a perfect equal to Gin despite the other's own capabilities and skill. Although he usually strays from battling, he can take on armies by himself and can win battles without wounds.
Charisma: Most of Takasugi's subordinates, including his closest, seem to have been won over by Takasugi's words, not actions. He recruited most of his men by finding those with similar ideas to him and brought up his goal of destruction to them, promising to assist if they desired the same. It's known that he did this to Okada Nizou and Itou Kamotarou, and it can be inferred that Matako was also pursued through a similar method. Despite how outlandish the goal is, there is not a single person who doubts his power.
Takasugi uses a katana, which he always carries with him, a shikomizue, which is a kind of concealed blade that, while lacking the tsuba, or guard, has a casing made of wood and on first glance isn't much different than the kind of sword Gin wields. However, Takasugi's sword has an actual blade and, furthermore, may be the blade he's had since his days in the Joui war.
Takasugi also holds some ability in playing the shamisen, as he has been seen playing it alone and with Bansai. It might just be a hobby of his.
- Yoshida Shouyou: Takasugi alongside with Katsura and Gintoki studied under Shouyou until their beloved teacher was executed during Kansei Purge. The three students would later see his execution and received the decapitated head of their teacher. Takasugi deeply admires Shouyou and said he is unable to stand the world that took Shouyou away and act like nothing had happened, including Gintoki himself when he was forced to execute their own master by Tendoshu, under orders of Sada Sada. However, Shouyou sacrificed himself to save his students' lives. According to Nobume, Takasugi seeks to destroy what Shouyou has left.
Friends & Allies
- Kawakami Bansai: Due to his true identity being safe from the police, Bansai appears to be Takasugi's negotiator and mole as Bansai, being the songwriter and producer for Otsu, can access most news and information without being in any danger. Bansai appears to hold a second-in-command position as well, usually being at base while Takasugi is aboard the Harusame or the like.
- Kijima Matako: Matako is openly in love with Takasugi, affectionately calling him "Shinsuke-sama". Matako is also able to be in close quarters with him in ways one doesn't expect a ruthless warrior to allow. It's unknown if he simply has great patience for her, balances it out mentally due to her assistance, simply can't care, or actually has affection for her in return.
- Takechi Henpeita: Being the tactical adviser to Takasugi, Henpeita plays a more open, second-in-command role than Bansai. He appears to be in charge whenever Takasugi is absent and people follow his commands whatever they may be, and although again it's unknown how Takasugi feels, it appears there's a bit of respect for him if Henpeita is even allowed to disguise himself as Takasugi (as no doubt others have brought it up). Henpeita seems to have an approach of doing whatever is "best" for Takasugi, as some attacks towards Gin have been purely organized by the tactician.
- Okada Nizou: Used more openly to an end, Takasugi took up Nizou after finding him killing in the slums of Japan. Asking him to join his cause to destroy, Nizou accompanied Takasugi and even took up the Benizakura for their cause, despite the mechanical weapon slowly taking over the blind samurai. However, Nizou, with his ability to see "lights" within people, quickly discovered Takasugi's "light" aggressively shone with sorrow, hinting at desire Takasugi hides inside.
- Kamui: Kamui and Takasugi have a relationship mirroring and foiling that of Kagura and Gin's, and one far closer than any of Takasugi's other subordinates. While Kamui addresses Takasugi as a friend instead of a father figure and Takasugi seems to treat Kamui as both an ally and a tool, Takasugi shares many of Gin's regular replies: he doesn't seem bothered by Kamui's personality and addresses his flaws with little notice, they can act anywhere between close friends (the Shogun Assassination Arc's first two chapters) to purely antagonistic (see the 3-Z books where they were enemies), and from their first meeting to the recent chapters the two play off each other and continue analogies, if just with minor enthusiasm on Takasugi's side. At the end of the Shogun Assasination arc, Kamui was even assisting Takasugi out of the battlefield and the Yato believes that Takasugi will not fail in his mission. As well, since their meeting up, the anime openings began to show Kamui standing close to Takasugi, revealing their bond of trust even there.
- Abuto: While Takasugi and Abuto aren't seen together very well, it's implied that Abuto is simply following along Kamui since he seems hesitant about working with Takasugi. It's possible that he was the one that tipped Takasugi off about Zenzou faking his murder of the Shogun, however.
- Sasaki Isaburo: Not much is known of the relationship between the Kiheitai and the Mimawarigumi, but before they went undercover after Shige Shige's death caused by Nobu Nobu and Tendoshu, by siding with Nobu Nobu and Tendoshu themselves, to stop their reign in aiding Katsura's Joui faction and Shinsengumi, it was known that Isaburo and Takasugi were on friendly terms, enough to where Takasugi could play along with Isaburo's visual gag of fishing up Nobume. Isaburo may have similar goals in mind to Takasugi, thus their partnership, but according to Nobume, the Mimawarigumi chief intends to see through Takasugi's "lies".
- Sakata Gintoki: They once studied together in his childhood and fought together in the Joui War but now they had gone on different paths, Takasugi wants to kill Gintoki because he sees him as the obstacle of overthrowing the Bakufu, he also hates to be called their former comrade. Gintoki often mocks him about his family position and army during the war. Gintoki would also make remarks about his height, which would probably be the reason for their rivalry.. His hatred towards Gintoki largely stems on Gintoki's choice of killing Shouyo to save him and katsura when the Tendoushu forced him to choose between killing Shouyo to live or die with Shouyo. But deep down both him and Gintoki know the hatred was directed at his weaker self who were unable to save their beloved teacher and was made to live by stepping on the teacher's corpse.
- Katsura Kotarou: In his childhood, Takasugi and Katsura were always at odds but even then Katsura thought of him as a comrade. They were consistently close friends throughout their time and, even when Takasugi begun his streak of antagonism, Katsura did not consider him an enemy until the Benizakura Arc, and eventually the two become allies once more after finding out Shige Shige's assassination was Tendoshu and Nobu Nobu's plan. Prior to it he began to remember Gintoki's saddened face with his last left eye and realized that it was their master's choice to pass them his legacy to live on if he died. He was willing to offer his head to Harusame, along with Gintoki's. Despite this all, though, Takasugi always calls Katsura "Zura".
- Tokugawa Sada Sada: Upon finding out that Sada Sada was the one whom started the Kansei Purge, resulting in the events of Tendoshu forcing Gintoki into killing Shouyou for the sake of his and his former allies' life, Takasugi begans to hates him most of all compared to his hatred of the Amantos, the government and his former comrades Gintoki and Katsura, before he reconcile with his former allies. He hates him for what he did to Shoyo, so he decided to kill him when he found out that he was at a weakened state for being a shield for Gintoki, to block Oboro's poison needles during an incident, and locked in prison and went in disguised as a member of the Tendoshu. Before he killed him, Takasugi told Sada Sada to send greetings to Shoyo.
- Oboro: During the Joui war where he went to stop Gintoki from beheading Shoyo, Oboro stops him by throwing a katana at his left eye. When they finally meet again in the present, Takasugi gives him a payback to Oboro, after what he did to his left eye in a past during Shogun Assassination arc.
- Hitotsubashi Nobu Nobu: Originally, Takasugi and Nobu Nobu are working with each other. Takasugi says that he will keep standing alongside Nobu Nobu as long as he keeps opposing the bafuku and that no matter which path Nobu Nobu takes, the one to kill him the end will be either Gintoki or Takasugi. This agreement comes to an abrupt end after Nobu Nobu joins sides with the Tendoshu after Kamui severely injures him.
First Appearance and Gengai Arc
Takasugi first appeared in flashbacks, but wasn't mentioned. He is first seen on Lesson 13's 18th page, standing beside Sakamoto (who, as well, wasn't introduced yet) with signs of his bandage absent and his eye hidden with hair. Katsura or Gin never make mention of him.
When Takasugi first officially appears, he first appears before Katsura before a festival celebrating the Amanto's first arrival comes on, revealing a similar relationship to him that Gin has through the unified nickname of "Zura". Although both men are disliked by the Bakufu, they both appear in public, but Katsura outright states that Takasugi is "hated by the Bakufu more than [Katsura] is" and that Takasugi was previously staying in the Kyoto area. Takasugi returns the remark by replying that he wouldn't miss the up-coming festival, suggesting he's planning on killing the shogun there. However, he adds that he "doesn't plan on doing something outrageous", but remarks it may happen and, if it did, it would overturn Japan.
True to what he said, Takasugi himself doesn't engage. He stands by, likely watching Hiraga Gengai prepare his robots with the assistance of the Yorozuya Gin-Chan group, which is how he learns of Gin's presence at the festival. Despite being covert, however, the Shinsengumi are deployed at the festival on Hijikata Toushirou's instinct, as the police officer believes a man who has killed multiple Bakufu officials and has been involved in multiple terrorist actions will appear.
As Gengai does his fireworks display, Takasugi sneaks up behind Gin and comments that "festivals aren't fun unless they're flashy". Caught off-guard by his old friend's voice, Gin attempts to draw his sword only to hear Takasugi draw his, the terrorist bearing his blade and poking fun at Gin's failure to defend himself. Takasugi slips that he knows Gengai's son died during the war, then further reveals he knew the son, Saburou, personally: Takasugi once led a volunteer cavalry during the war, and Saburou worked under him until his beheading by the Bakufu. Gin connects the dots, but Takasugi denies "inspiring" Gengai, instead "telling him to sharpen his fangs" due to sympathy out of feeling the same way.
With an idea in mind, Gin uses Takasugi's distraction for his own advantage, grabbing a hold of Takasugi's blade with a bare hand while he wasn't paying attention. Using this to hold Takasugi still, Gin punches his old friend and makes a break for it, moving to get over to Gengai and convince him out of causing more of a mess. Although fine, Takasugi escapes, acknowledging his plan was foiled. After the festival, he found by Katsura and the two discuss Gin's "fangs", with Takasugi revealing he believed they had been lost whereas Katsura states everyone has fangs when they protect something.
Interestingly enough, his next appearance wouldn't be for another 59 chapters, but in the popularity poll in between, he landed in 4th with exactly 1,500 votes. As well, he is seen carrying a gourd canteen when he jumps Gin, implying he actually was enjoying the festival.
Although Takasugi himself doesn't appear, his subordinate, Okada Nizou, did. Depending on the translation, a passing reference is made to Takasugi, as Nizou compares Gin's scent to his employer's as both being beast-like.
Takasugi again resurfaced in Edo during the Benizakura chapters. This time, he didn't come alone: he had brought Kawakami Bansai, Kijima Matako, Takechi Henpeita, Nizou, and the rest of the Kiheitai with him in order to stage a military coup and forcibly overthrow the Bakufu, but from the looks and sounds of it, they were simply ported in Edo in order to test Benizakura and gain information on it, as the bio-weapon required in-battle data to become a true weapon. Using the help of Murata Tetsuya, who created the Benizakura swords, he gave Nizou the first blade and more or less sent him off to gather data. However, Nizou begun to target random samurai and assassinating them in one-strike sword battles, eventually attempting to take down Katsura. While he did fail, as the book Shouyou gave to all his students ended up saving Katsura and taking most of the slash, it's hinted at that Takasugi was a little upset with this move - whether it was because Nizou was attracting attention or because it was Katsura is unclear. It may be more of the first, though, as the rest of the Kiheitai were upset Nizou recklessly garnered attentionTakasugi threatened to cut through both Nizou and the sword if Nizou ever called Gintoki and Katsura his "comrades" again, as he claims that their relationship wasn't nothing that sweet
In search of Katsura, Kagura found and faced off against Takasugi for a brief moment under the light of the full moon. She didn't attack due to her instincts alerting her of Takasugi's "dangerous smell", and she was swiftly attacked and captured by the combined efforts of Henpeita and Matako. Takasugi silently watched the battle and appeared to have made no orders concering Kagura or Nizou, who had returned to the base missing an arm, as Nizou was left alone and Kagura was next seen tied to the wall presumably for information, though honestly no one there knew who's side she was on (as Takasugi never saw her alongside Gin until after this arc).
As the Joui patriots under Katsura attacked in revenge, Takasugi had disappeared to monitor the Benizakuras alongside Tetsuya and had made a quick stop to speak to and threaten Nizou. On deck, as the firefight raged on, Kagura was put up as a hostage only to be fully ignored. He did eventually reappear, though, when Shinpachi (who had hopped upon the ship himself to save the Yato girl) and Kagura were hoisted back on deck by Elizabeth, slicing through the head of the penguin mascot. Though he states this "isn't a venue for cosplay", he's surprised that Katsura was under the costume and is nearly cut down by his former ally.
Katsura reveals he had been on deck this entire time, watching from the shadows and studying Takasugi's plot. It's revealed that Takasugi was also protected by the blunt of the attack through Shouyou's book, and the two idly chat abou Nizou's failure before a bomb Katsura set up goes off. In the confusion resulting form that and the Joui patriots boarding the ship, Takasugi escapes back inside with Matako and Henpeita, his subordinates holding Shinpachi and Kagura back. He rests for a bit, finding a balcony from which he can watch Gin battle Nizou, and he idly chats with Katsura again. He reveals to his old friend his contemplations about the world and being a samurai, stating he can't see anything but a path of destroying the Bafuku, and he exposes the source of his pain: the world they live in now took away Yoshida Shouyou, his former teacher, and because of that his burning hatred will lead him to do anything to take revenge.
Although Katsura tries to pull Takasugi back, stating he's upset as well but now has things to protect, the Amanto appear as Takasugi's allies. Explaining that he heard both Gin and Katsura had gotten into an altercation with the Amanto earlier, he offered his assistance in taking their heads for their gunpower and manpower. Reinforcing that all he wants is to destroy this corrupted world, he flees his burning and battered ship with the rest of the living Kiheitai members onto the Harusame flagship, only sticking around long enough to see Gin and Katsura promise a battle the next time they met.
The bomb Katsura set up and the multiple wounds the boat suffered from the air battle that surrounded the ship caused the loss of the main Kiheitai ship. Through losing the ship, Takasugi also lost the Benizakura swords and some manpower, which caused his disappearance. Yamazaki backs the claim by reporting to Toshirou several chapters later, stating that both the Kiheitai Faction and the Joui Faction both lost enough man power to cause their respective retreats from the public eye.
Much like with Nizou in the Infant Strife Arc, Bansai appears and makes multiple references to him, revealing Takasugi's plan through conversations with Yamazaki Sagaru and Gin. Depending on whose word you take, Bansai or Shinsuke's, the ultimate goal was to lure the Shinsengumi away from the Bakufu, allowing the Harusame an opportunity to sign a truce with the top authorities that likely would've ended in an eventual degradation and destruction of the government, or what Takasugi wanted, absolute destruction of the Shinsengumi.
According to bits of information offered by Bansai, when Itou appeared before the Kiheitai, Takasugi quickly formed an idea to use Itou's rebellion plan for his own advantage: destroy the Shinsengumi through a disruption in their ranks and then kill Itou, as the Kiheitai (according to Bansai) has a personal policy on not dealing with those easily capable of betrayal as members like that may easily become double-edged swords. Then, either to earn Itou's trust or to have someone keep an eye on everything, Bansai was ordered to follow along and respect Itou's orders whenever given and Itou was allowed use of the Kiheitai manpower.
After the battle, which ended in Itou's death and Bansai himself nearly getting crushed by a helicopter, the swordsman of the Kiheitai returned back to base and greeted his true boss. Takasugi, seen playing a shamisen, comments that the Bakufu government is strong and chides both his subordinate and Itou for being weak. When Bansai reminds Takasugi of the plan, Takasugi replies that the mission was to destroy. When Bansai leaves, he states that the things Gin fights for "remains the same" and that he shows interest in hearing the rest of Gin's song. As Bansai leaves, Takasugi looks on in disdain and continues to play his shamisen.
In Lesson 173, it's brought up that, due to the battle, enough man power was lost to weaken the Kiheitai enough to cause inactivity.
In the aftermath of the Kabukichou Four Devas arc, Takasugi is shown on the main Harusame ship, likely making more dealings for assistance. However, the Admiral of the pirates at the time, Admiral Abo, sent Kamui to eliminate him due to Takasugi's reoccuring habits of following his own plans. Although it was revealed to eventually be a ruse to kill Kamui, as the Admiral feared that he'd be overthrown if Kamui stuck around, the Yato's endurance prove to be the undoing of the whole event: because he withstood being periced by poison arrows and being struck by Takasugi's sword, Takasugi had the chance to recruit Kamui by taking him up on an offer of being allowed as much destruction as he wanted.
In Kamui's public execution, Takasugi broke the bonds holding Kamui and sided with him, taking on the Harusame with the Yato by his side. When Squad 7 and the Kiheitai got involved in a growing brawl, Admiral Abo fled and was soon caught by and killed by Kamui. With Harusame now in control of Kamui, the two became allies in a temporary truce (as Kamui showed interest in battling and killing Takasugi and Takasugi wanted to use Kamui as a weapon) and the Yato under Kamui's control begun to follow the orders of the Kiheitei.
It's revealed during this arc that Henpeita regularly disguises himself as Takasugi in order to issue commands, or to fool his subordinates into believing he's around in order to cease worriment or something of the sort. Whether or not Takasugi approves of this is unknown, but it's possible he may since Henpeita ends up doing this multiple times later as well as having a megaphone shaped like Takasugi that can change someone's voice into Takasugi's.
Beginning a long history of appearing only at the end of arcs, Takasugi meets up with Sasaki Isaburo as the police chief is literally fishing for his subordinate, Imai Nobume. Noticably Takasugi refers to Sasaki with the honorific dono, showing respect he otherwise wouldn't give. Sasaki speaks about how he realizes he, the Bakufu, and everything else is on the edge of "crumbling away" and after stating he's already accepted the idea of becoming bait, Takasugi leaves with a smile with the promise to turn the sea of rubble that is Edo and transform it into a vacant lot. Although they, all in all, state plans to work together, it would be quite a while to see this in action.
Irony strikes Tokugawa Sada Sada, who believed he could escape from jail without death. Disgusing himself as a Naraku agent, Takasugi slips into the jail Sada Sada is confined in and visits. Stabbing Sada Sada, he states he'll judge him and, with even more irony, accidentally requotes Gin from several chapters ago. With the words "Give my regards to Sensei for me", Takasugi slices the head off Sada Sada and disappears before the Shinsengumi can catch him.
Nobume states that she and Isaburou would be joining forces with Takasugi, but she chastises Oboro for doing the same. When asked if they're similar to Shouyou, Nobume says that Takasugi is "seeking to destroy what he had left". Noticably, while she's saying this, the panels cut to reveal Gin and Takasugi (in his normal kimono) walking by each other in the street, with only Gin bothering to look back.
Sakamoto and Katsura organize a reunion for the members of the Joui Army, inviting Gintoki and Takasugi in an attempt to kickstart a "Past Arc" where they could all finally be cool together. However, Takasugi himself never really appeared, mostly because his subordinates intercepted the invite and never told him about it. Instead, Henpeita comes in his place, falsifying letters from Takasugi and then proceeding to use the mysterious fifth member, Kurokono Tasuke, and Gin's fear of ghosts to kill them off and help further their leader's plan. It's unknown if Takasugi actually would've come or not, or if he even remembered Kurokono, since nothing was passed by the Kiheitai leader.
In the Joui flashbacks, however, Takasugi is a constant element, since most of the conversation ended up becoming about him. It's seen that he has a rivalry with Gin and that they ended up fighting about a lot of things while not in war, like choosing girls in red light districts (and if he won, Takasugi spent the whole night drinking away) and childishly playing Kick the Can with everyone with outrageous enthusiasm. The running joke was how he had an obsession with Yakult, from sending a large supply of it to the New Years Party from threatening Sakamoto into drinking it, which left a large impression on the fanbase since it was the first time Takasugi was, since his introduction, the butt of a joke.
It should be said as well that Gin, Katsura, and Sakamoto were easily fooled into believing Takasugi had left them threatening-looking messages like "I'll pay for the Yakult at this party too; go drink with Shirako all you want" and the like, as well as Gin saying that Takasugi is the kind of person who'd go to a reunion only to play on his phone the entire time and quesitoning his abilities at writing letters.
Takasugi's habit of only appearing at the end of arcs comes back as he appears before Hitotsubashi Nobu Nobu, smoking his pipe. He comments tha Nobu Nobu will never take his or Gin's head, but the other man seems more interested in Takasugi's desire for destruction than killing him. Their words imply partering up, but as Takasugi leaves, he warns that Nobu Nobu will either face Gintoki if he opposes the government or Takasugi if he joins their side.
The Shogun Assassination Arc features the first time Takasugi appears at the very beginning, but in usual circumstances. As Nobu Nobu states he plans on removing Tokugawa Shige Shige, he hears someone coming from behind and believes they're the "new limbs". However, it is Kamui, delivering a punch that sends Nobu Nobu flying. Takasugi appears shortly after, addressing Kamui's mistake with the same attitude Gin would to Kagura: Kamui says that, since Nobu Nobu is the "next Shogun" and they were wanting to kill the "current Shogun", they were one in the same because both of them were "a Shogun". In response, Takasugi sighs and comments that Nobu Nobu probably won't remember anything (considering he's now lodged in a wall across the street) and he says that Nobu Nobu is simply another one of Takasugi's "limbs".
Kamui and Takasugi talk, revealing that they've gain a close relationship inbetween the arcs. Takasugi tells Kamui that, even if Nobu Nobu is weak, he is who they're trying to enstate as Shogun and if anyone makes a wrong move, it'll end with Nobu Nobu's head being cut off. At the very least, Kamui critically injuring Nobu Nobu has averted all eyes from the Hitotsubashi, so Takasugi treats it as a good thing and they prepare to attack. 
Seemingly aware of the plan to use multiple Shogun doubles to protect the real Shige Shige, Kamui and Takasugi split up, with the Yato forces attacking the flying ships while Takasugi splits his men to attack the Shinsengumi troupe, the fleet of boats on the ocean, and the palace al at once, with Takasugi taking Matako, Bansai and Henpeita to fight the naval battle. As well, to top it off, many Kihentai members are aboard or within the four groups, seemingly defecting in order to attack from the inside. Kamui comments that Takasugi and he are in a contest to claim the real Shogun's head, but as usual it's unknown how Takasugi himself feels.
Takasugi's invasion of the naval fleet is a success, with his subordinates quickly killing enough men to make a path to the Shogun. Although he realizes it's a fake, Takasugi still kills everyone in the room and reveals to the faker that what he wants is to destroy the entire Bakufu, a reinstatement of his earlier plans from the beginning. When asked for a ringleader, Takasugi makes an interesting comment: that he's in Hell.
- Takasugi Shinsuke is based on the real Kiheitai leader Takasugi Shinsaku, a samurai who founded and commanded the Kiheitai in an effort to fight against the Bakufu. His actions eventually lead to the Meiji Restoration, but he died before he could see it through.
- In all versions of Episode 150 he appears as the final enemy, in a battle against Gintoki while Edo is burning, but this is proven false because he joins forces with Kamui.
- In the manga, Takasugi's yukata is a complicated pattern of mountains, flowers and fog, but in the anime it was turned into a very simple-looking yukata with yellow butterflies and a "fog" of yellow at the very end. His jacket, however, remains a constant: a dark green jacket carefully patterned with gold swirling lines.
- In the popularity poll, Takasugi is placed 4th in the first and second popularity poll and in 5th during the third popularity poll which makes him one of the most popular characters even though he barely appears. Furthermore, although Takasugi is often brought up, is the largest known villain, holds a connection with most of the main characters, and holds probably the most destructive potential, he never appears in any filler episode content unless in flashback or as a joke. As such, other characters take his place when he's needed: Madao dresses up as him in the Popularity Poll arc, Katsura in the second movie, and Henpeita when Takasugi is away or somewhat important to the plot.
- However, in chapter 454, Matako outright states that no one told Takasugi that a reunion was being held, so it could be said his previous absences are simply because of communication failure.
- A part of his popularity may come from who voices him in the show: Koyasu Takehito, who has voiced well over four hundred characters and is currently one of the most prolific voice actors around.
- Takasugi has the same voice actor is Aokiji from ONE PIECE, Ryouji Fujioka from Ouran Koukou Host Club and Sister from Arakawa Under the Bridge.
- (To Sakata Gintoki) "I know his suffering, after all the black beast of vengeance lies within me as well."
- (To Katsura Kotarou) "I'm fine with being a beast, I neither want nor need anything to protect. I just want to destroy everything, until the beast stops whining."
- (To Admiral Abou) "It's better to be the head of the cat than the tail of a lion. I'd rather be a bandit chief than a pirate or bigwig."
- (To Kamui) "It's more fun to dance with a batshit crazy idiot, than a plain old idiot."
- (To Katsura Kotarou) "Zura...The sword in your hand...who taught us how to use it ? Our samurai code, our way of living. Who taught us these ? The one who gave us a world to live in, was without a doubt...Shoyou-sensei. Yet, this world... took him from us. In that case, we have no other choice, but to fight this world. We have to completely destroy...this world that took him from us. Hey Zura...how do you feel living in this world? In this world that took our teacher away from us. How could you live in it, in such a carefree manner? It pisses me off!"
- (To Kawakami Bansai) "Bansai. Can't you get into the groove of my song?"
- (To Admiral Abou) "You're the one who's no longer needed. Didn't you hear me? I'm the executioner here, the only executioner needed in this place. Off with your heads."
- (To Sakamoto Tatsuma) "I bought you some damn yakult. So shut the hell up and drink it!"
- (To Hitotsubashi Nobu Nobu) "I'm touched by your having such a high estimation of me. As long as you are opposing the bakufu, I'll keep standing here. But the moment you gave up on that it might be that the ones bitting at that neck may be him (Gintoki) or me."
- (To Kamui) "I'm like you...searching for a place to use my sharpened fangs,but this leaky boat won't take me anywhere."
- "Have a nice nap in hell...leaky boat crew!"
- (To Okada Nizou) "Don't label us as comrades,our relationship isn't that simple."
- (To Tokugawa Sada Sada) "That's right.You won't be judged by the shogun or the heavens.You will be judged...by me.Don't bother trying to remember me, cause I'll bring the Tendoshu and those worthless crows,no...I'll bring the heads of every person on this planet down to hell with me....Say hello, to sensei for me."
- (To a ninja) " We never had all that much interest in that from the start. What we've been really seeking is not his head. It's you guys. The Shogun's limbs. Hit or miss, if we pull up all the roots, the head will fall on its own. "
- (To a ninja who asked him about his ringleader) " He's in Hell. Where you're about to go. "
- (To Gintoki when realize he realized why his old friend was saving him and Katsura, instead of Shoyo in the past. Shortly before Oboro arrives and impales him) "I see... Looks like I wasn't expelled from that school after all."
- (Response Gintoki's words to Oboro on "never dare" to) "... talk about Shoyo."
- (To Oboro after stabbing him in the eye) : " Make sure...you burn that into your memory as well. The last face that eye saw. Me or him? Even if one drops dead here the other one will definitely send you to hell."
- ↑ Chapter 516, page 16
- ↑ Chapter 517
- ↑ Chapter 518, page 3: "That's 247 wins and 246 losses."
- ↑ Chapter 29
- ↑ Chapter 95
- ↑ Chapter 453; "I made sure to take note of the fact that the girl liked Takasugi better. Hey, was that when you guys started fighting?"
- ↑ Chapter 453; "No suddenly, they're really on board! Even more than they are with the war!"
- ↑ Chapter 94, page 4
- ↑ Chapter 310, page 13; Even though it isn't Takasugi himself, it should be noted that Matako had no problem openly hugging who she thought was her boss.
- ↑ Chapter 93
- ↑ Chapter 454, page 9
- ↑ Chapter 95
- ↑ Gintama Manga: Lesson 477, page 8
- ↑ Lesson 13, page 18
- ↑ Lesson 29
- ↑ Lesson 30, page 16, top panel; it's seen again on the 6th page of the following chapter, held in the same hand.
- ↑ Lesson 78, page 7
- ↑ Lesson 91, page 18
- ↑ Lesson 95, It's his own desire to [wield Benizakura]. If he dies while doing this, it would be a personal wish fulfilled.
- ↑ Lesson 93, page 10
- ↑ Lesson 92, page 9
- ↑ Lesson 93
- ↑ Lesson 95
- ↑ Lesson 97
- ↑ Lesson 164, page 18
- ↑ Lesson 168
- ↑ Lesson 370
- ↑ Lesson 398
- ↑ Lesson 453
- ↑ Lesson 468
- ↑ Lessons 502 and 503