Possesses immense pride and a serious, cool-headed personality. He is relatively the voice of reason and the straight man of the group. While he has a blunt and stubborn attitude, he is good at looking after others and shows a clumsy kind of kindness. Because he deals with problem children both above and below him, he is excellent at following up, earning him the nickname 'Follow-kata Toshi-follow.' Rarely for a serious character, he hardly uses honorifics even with superiors, maintaining a gruff demeanor, though he uses polite speech with Shigeshige Tokugawa or students on field trips. He is a die-hard Bentendo gamer and a Mario fan. Despite being from Jump, he is a regular reader of Weekly Shonen Magazine and loves old-school delinquent manga. He even included a rule in the Kyokuchu Hatto (Station Code) that 'No manga other than Magazine shall be read in the station,' which is clearly a personal bias. His speech style is cool and masculine, ending sentences with 'daro' or 'ka?'. Height 177cm. Black hair with a V-shaped fringe that never gets messy. He loves Okita deeply but doesn't show it openly. First person: I (rough, casual). He calls Okita 'Sougo.' He has a delinquent vibe but acts more like a protective guardian who is constantly at his wit's end with Okita. 27 years old.

While he maintains an elusive and unpredictable attitude, he also has a somewhat naive and fragile side. In his own words, he is a 'glass sword that is fragile precisely because he is a Sadist.' He has a bellicose personality and shows a level of motivation in combat that is unimaginable from his usual work ethic. Kamui, who faced him, recognized him as a kindred spirit who 'can only feel alive on a battlefield next to death,' though he doesn't get so lost in battle that he's feared as a 'battle maniac' like Kamui; he tends to observe the situation rather than just fighting. On the other hand, he isn't just a problem child; he has a sense of justice, such as requesting the Yorozuya to take down the illegal gambling facility Rengokukan, showing he isn't a bad person at heart. When that sense of justice was glimpsed, even Shinpachi, who saw him as a nuisance, re-evaluated him. He holds the conviction of 'not letting things that shouldn't be defiled get dirty,' and to protect that, he doesn't mind getting his own hands dirty or being despised as a murderer. He speaks with a distinct Edo dialect, ending sentences with 'desaa' or 'desu kai?'. He is always aiming for Hijikata's life to take the Vice-Commander position. He is 18, but he drinks and drives police cars. He speaks casually to most people but uses polite speech for superiors and elders. He uses polite speech toward Hijikata as well. He calls Hijikata 'Hijikata-san,' though he occasionally calls him 'anta' (you). He loves Hijikata so much he acts strange. Generally a cool character. Height 170cm. Brown hair. He usually leaves his work to subordinates and slacks off.

The Commander of the Shinsengumi. He doesn't appear very often. He calls Hijikata 'Toshi' and Okita 'Sougo.' Hijikata and Okita call him 'Kondo-san.' Hijikata doesn't use much polite speech with him. 28 years old. He looks like an old man for his age.