Shinpachi Nagakura serves as Captain of the Shinsengumi's Second Division. Hailing from Edo where his father was a Matsumae clan retainer, he exhibits an upbeat, cheerful demeanor that bolsters troop morale, frequently engaging in boisterous social activities like drinking with close comrades Harada Sanosuke and Toudou Heisuke, forming a rule-breaking trio. Despite this outwardly carefree nature, he possesses significant political awareness and clear convictions, openly challenging leadership decisions. He takes pride in his muscular build and maintains exceptional swordsmanship skills honed at the Shindō Munen-ryū school alongside figures like Serizawa Kamo. Initially aligned with the Shinsengumi's ideals, Shinpachi participates in critical missions including the Ikedaya raid and the Kinmon Rebellion. During the Ikedaya incident, he protects Chizuru Yukimura from attackers while wounded, later allowing her to tend his injuries, marking the beginning of their trust. He reacts vehemently to perceived disrespect towards the Shinsengumi, confronting Aizu soldiers who attempt to sideline the group. As conflicts escalate, his pragmatism emerges; he supports adopting Western firearms and uniforms to counter modernized enemies but grows disillusioned with Commander Kondō Isami’s ambition to become a feudal lord, adamantly rejecting becoming a retainer and valuing his autonomy. Tensions culminate during the retreat from Kōfu Castle. Shinpachi and Harada oppose Kondō’s plan to assault the castle against overwhelming odds, citing new recruits' inexperience. After Kondō accuses him of cowardice, Shinpachi nearly attacks his commander before being restrained. Following defeat, he privately confronts Kondō about leadership failures and decides to leave the Shinsengumi, joined by Harada. They bid emotional farewells to Heisuke and others, Shinpachi explaining his refusal to serve under a lord not of his choosing. Though parting ways with Harada shortly after, he later temporarily rejoins former comrades during the battle at Utsunomiya Castle, aiding Hijikata Toshizō and sharing a reflective conversation. In the visual novel *Kyoto Winds/Edo Blossoms*, Shinpachi’s route explores his relationship with Chizuru. Initially mistrustful, he demands proof of her gender and supports her execution as a security risk. Over time, he develops protective feelings, treating her like a "little sister" while gradually acknowledging deeper affection. His route highlights internal conflicts, including anguish over Heisuke’s transformation into a Rasetsu and refusal to consume the Water of Life himself. Key moments include sneaking Chizuru out for defiant group drinking, gifting her a brazier for warmth, and bonding over shared Edo roots. His stubborn yet principled nature drives choices prioritizing his men’s safety, even using himself as a human shield. The film *Warrior Spirit of the Blue Sky* depicts Shinpachi’s departure following the Shinsengumi’s decline. Disagreeing with Kondō’s tactics against the Satsuma-Chōshū alliance and their daylight-capable Rasetsu foes, he and Harada leave to pursue their own path. While not central to the film’s climax, his decision reflects his consistent rejection of compromised ideals. His ultimate fate remains ambiguous across most adaptations, though a final vision places him among deceased comrades. Historically, he survived the Bakumatsu conflicts, dying naturally in 1915.