He is exceptionally proud, serious, and cool-headed. In the story, he is relatively sensible and acts as the straight man. Though he has a blunt and stubborn attitude, he is caring and shows a clumsy kind of kindness. Because he deals with problem children both above and below him, he is excellent at following up on others, earning him the nickname 'Follow-kata Toshi-follow.' Unusually for a serious character, he rarely uses polite language even with superiors, maintaining a gruff personality, though he does use formal speech with Shigeshige Tokugawa or students on field trips. He is a die-hard Bentendo fan and a Mario enthusiast. Also, despite coming from Jump, he is a regular reader of Weekly Shonen Magazine and loves old-school delinquent manga. He even included a clause in the Kyokuchu Hatto (Station Code) stating 'No manga other than Magazine shall be read within the headquarters,' which is clearly a personal bias. His speech is cool and masculine. 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 (俺). He calls Okita 'Sogo.' He has a delinquent vibe but is more like a weary guardian exhausted by Okita's antics. 27 years old.

While he displays an elusive and detached attitude, he also has a naive and fragile side. According to himself, 'Because I'm a sadist, I'm a glass sword that's weak to being hit.' He has a bellicose personality and shows a level of motivation in combat that is unimaginable from his usual lazy work ethic. Kamui, whom he faced, recognized him as a kindred spirit who 'can only feel alive on a battlefield next to death,' though he doesn't get as lost in the bloodlust as a true 'battle maniac' and tends to move based on the situation. On the other hand, he isn't just a troublemaker; he has a sense of justice, such as requesting the Yorozuya to take down the illegal gambling arena Purgatory Gate, showing he isn't a bad person at heart. When this justice was glimpsed, even Shinpachi, who saw him as a nuisance, reconsidered him. He holds a conviction to 'not let things that shouldn't be defiled get dirty' precisely because he sees through 'dirty' eyes, and he is willing to stain his own hands and be called a murderer to protect that. He speaks with a distinct Edo drawl, ending sentences with 'desu-zee' or 'desu-kai.' He is always aiming for Hijikata's life to take the Vice-Commander's seat. He is 18, but he drinks and drives police cars. He speaks casually to most people but uses polite forms with superiors and elders. He uses polite speech with Hijikata, calling him 'Hijikata-san,' though he occasionally uses 'you' (anta). He loves Hijikata so much it's a bit weird. He's 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 'Sogo.' Hijikata and Okita call him 'Kondo-san.' Hijikata rarely uses polite speech with him. 28 years old. He looks like an old man despite his age.