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Relationships
There are many people who have crossed paths with Shishio and those who have even managed to have an impact on his life. Below you'll find a summary of a chosen few of them and the role they played in Shishio's life. I tried to make it as spoiler free as possible
 Kenshin Himura aka Battousai the Manslayer*
He is Shishio's predecessor and his major obstacle in taking over Japan. Too big of a threat for the government to handle, Kenshin was summoned by Lord Okuba to get rid of Shishio for good. Their former professions and tactical way of thinking may be very similar but their ideals are very far from the same.
 Aoshi Shinomori
The Oniwabanshu leader who has an obsession of becoming the strongest. Aoshi's goal involved defeating the Battousai as a means of accomplishment to garnish the graves of his fallen Oniwabanshu comrades. To achieve this objective he went as far as to form an alliance with Shishio under the condition that he would receive information regarding the Battousai. That proved to be to Shishio's advantage since the head strong warrior would have completed his dirty work for him, removing the obstacle that Kenshin Himura posed before him.
 Hajime Saito
He is the former leader of the third squad of the Shinsengumi and lives by the code of Aku Soku Zan. In the peaceful times of the Mejii era, he works as a police officer for the government. By the will of Lord Okuba and mostly on the will of his own, he decided it was best for Japan to be rid of Shishio as well. With the help of the Battousai, he bravely opposed him on a mission to cease his tyranny.
 Yumi Komagata
At the fall of the shogunate, Yumi used to be a very high class courtesan in Yoshiwara. She was familiar with the Red Light district's bright and flowery illusion and became tired of the world changing but the lies and pain always staying the same. She only experienced happiness when she met Lord Shishio. Even though Shishio seemed to be the embodiment of evil to the public eye, she saw something within him that no one else did. In a way, they related to each others opposition of the Mejii and his desires became her own. She is the gentle soul who fell madly in love with a tyrant and cares for him with the greatest of passion. Undoubtedly, he feels the same way about her also.
The Juppongatana
 Soujiro "The Tenken" Seta
Soujiro is Shishio's right hand man and probably the first of the Juppongatana to be recruited. He is a young assassin raised and trained by him and the most dangerous and most powerful of his allies.
Soujiro's constant, sweet, smiling face and kind manners stem from a very tragic past. He was the son of a prostitute who his father abandoned in the care of his family. He was badly treated and forced to slave over all the household chores as a result of being the son of a whore. To shadow his never ending sadness and pain, Soujiro's only means of defense was to always show a smiling face when subjected to the constant physical and verbal abuse. It was only then that they eventually let him be.
Soujiro first met Shishio when he bearly escaped an assassination attempt by the government. He sheltered him, aiding him with food and bandages, welcoming the company of the alluring man. That was when he learnt the first rules of life he came to live by "If you're strong you live, if you're weak you die". With that mentality, Soujiro slaughtered his oppressors, who had tried to murder him for housing the branded killer. From then, Soujiro traveled with Shishio becoming his apprentice, and right-hand man.
Soujiro's apparent lack of emotion makes him a formidable opponent. He wields the legendary sword Nagasone Kotetsu, and the Shukuchi he utilizes has such powerful speed that, to an observer, it appears that the distance between the two fighters has shrunk (hence the name Shukuchi "reduced earth"). Combining true Shukuchi with the Battojutsu he created the Shun Ten Satsu (Instant Heaven Murder), named this because the speed behind the attack is so swift that "there isn't an instant even to feel the pain."
 Houji "The Knowledged" Sadojima
Hands down I would have to say that Houji was the most faithful of the Juppongatana. His admiration and loyalty towards Shishio was truly unwavering. Other than Soujiro and Yumi, he would be considered the next in line to be closest to him. More than anyone else, he savored the same ideals as Shishio deep within his heart- the longing to have Japan under a more appropriate leadership, one such as him. Though not proficient in any style of fighting, Houji proved himself to be truly beneficial to the antagonist aiding tremendously with his cunning organizational skills and strategic wisdom. Without Houji's assistance, it is likely that Shishio's tyranny would not have proved to be so successful.
 Usui "The Blind Swordsman" Uonuma
Usui used to work for the shogunate about ten years ago until he encountered a fight with Shishio during the revolution and was blinded. As a result, he learnt to adapt his other senses, especially his sense of hearing, which allows him to use the "Eye of the Heart". It enables him to hear another's heartbeat thus allowing him to sense those around him and their emotions. The friction of bone and muscle allows him to tell the enemy's attack stance. He has a knack for the senseless killing of those weaker than him in order to boost his ego and to fill the void and ease the frustration of his loss to Shishio. Usui joined the Juppongatana under the condition that he can attack Shishio whenever he pleases, hoping to gain a moment when he is most vulnerable. However, Hajime Saito saw right through his true intentions and threw it right back in his face infuriating him. His intention was not to kill Shishio because he had given up on seeking revenge a long time ago. By gaining the "Eye of the Heart" he had believed he became stronger but upon encountering Shishio again, he had realized that the death matches Shishio had encountered made him even unbelievably stronger as well. He knew that if he fought him, defeat would be inevitable and if he lost his life everything would have been for nothing. So he accepted the offer to become a member of the Juppongatana under the one condition that he can slay Shishio when his guard is down. He knew it would be impossible to kill him unless he waited for a precise moment of vulnerability. As long as he kept up the bluff that he was going to kill Shishio, no one would ever realize his defeat. However, Shishio did realize the wounds of his cheap pride and used that to manipulate him to do his bidding. Such perception and intuition should never be overlooked from a man like him, Usui's biggest mistake. Usui fights using a short spear called the rochin and a tortoise shell called timbei used as a shield. Both are of the royal martial art of his homeland of Ryuukyuu. The timbei uses the shell's roundness to deflect the enemy's weapon while at the same time blocking the enemy's vision and then he uses that opportunity to pierce with his rochin. One of his martial art techniques is called Bouken Bougyoku Hyakka Ryouran (Treasure Sword, Treasure Sphere, Hundred Flower, Silver Chaos) which is a series of rapid thrusts with the spear's point and ball.
 Anji "The Destroyer" Yukyuzan
Anji is a warrior monk on a path of vengeance against the Mejii government who did nothing to stop the anti-Buddhist purge that destroyed his home and loved ones. To achieve his objective of destroying the system he teamed up with Makoto Shishio under the condition that he decides whether someone lives or dies. He is the most merciful of the Juppongatana, very strong in build and combat ability. His combat skill is a technique called the Futai no Kiwami (Double Layer Limit) which surrounds the use of his fist. The only time he uses a weapon is when he utilizes a blade by striking it into the ground causing a huge vibration to attack an opponent from a distance.
 Cho "The Sword Hunter" Sawagejo
Cho is an interesting guy who has a very strong devotion to collecting rare or unusual swords. He can be a daring opponent according to the sword type he uses, but other than that his sword skills can be considered mediocre. His sword fighting style is called the Garyuorochi, which utilizes a few alternating techniques. There is the Orochi in which he bounces his sword, the Hakujin no Tachi which utilizes a blade so thin that it can twist and manouvre around an opponent making it hard to deflect. And then there is Sakaka Kuchu Noto, which involves a remarkable midair unsheathing of the sword. It was illustrated on Seiku's son Iori to locate the final sword of Shakku Arai.
 Kamatari "The Great Scythe" Honjo
Kamatari is the cross-dresser who has an avid adoration for Makoto Shishio. He always thought that he fit somewhere right in the middle regarding Shishio, never being his right hand man like Soujiro or his best woman like Yumi. That's why he fought extra hard to show his devotion on every mission he was assigned to. Kamatari's weapon of choice is a reaper with a chain ball attached to the butt of the stick. It is an extremely heavy weapon with immense power, which has the tendency to leave the user unguarded for a few seconds. However, Kamatari makes up for this, using techniques interchangeable between the scythe and chain making his strategy appear to be flawless. He practices Honjoryu and one of his most powerful attacks is the Midare Benten executed when the scythe is whipped over the head also swinging the chained ball into a sphere like motion. It combines offense and defense slicing away at anything it touches.
 Hennya "The Flight" Hariwa
Hennya is the most unusual of Shishio's pawns. He utilizes aviation abilities with the aid of bombs that propel him into the air. He is bone thin causing him to be very light and he uses a cape to glide him steadily. Hennya has little combat skills except for the bombs he uses to attack, swooping down to swipe at his enemy when necessary. And since he uses the explosions to his advantage as a means to keep him airborne, his enemies have little means in retaliating to attack him. He refers to his fighting style as the Hikku Happa.He assisted with setting the fires in Kyoto and the attack on the Aoiya**.
 Rojin Saizuchi and Fuji
Saizuchi is the captain of the destruction army and manipulates Fuji to do his bidding. He is a very short man with yellow teeth and a mustache in the shape of whiskers. He took Fuji under his wing when everyone else treated him as an outcast because of his giant stature and molded him into a fighter of unbelievable skill. They assisted with the attack on the Aoiya.
 Iwanbo
Iwanbo is the fat, clueless member of the Juppongatana whose only skill requires the use of his immensity. If not for that, he will not be of any use at all, once you subtract his ability to entrap weapons and bounce off attacks on his flab. Surprisingly, he assisted with the attack on the Aoiya
*Kenshin has a very huge background so I chose not to go into too much detail regarding the character.
** Aoiya - The Kyoto base of the Oniwabanshu
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