Reincarnated from Imagawa Yoshimoto, a powerful Sengoku daimyo ruling Suruga Province and one of the Tōkaidō's three dominant warlords, Imagawa Gilbert Yoshimoto now lives as a small brown Dachshund. His former life ended in 1560 during the Battle of Okehazama, where Oda Nobunaga's forces killed him while marching toward Kyoto.

This modern canine possesses long, fluffy ears and distinct rhombus-shaped patches of lighter brown fur above his black eyes and around his snout. He wears a white waiter-style collar featuring a smart blue bow. Yoshimoto displays a self-assured personality, believing himself more talented than others perceive and reflecting on the profound nature of man's world. He harbors no lingering resentment towards Oda Nobunaga, reincarnated as the Shiba Inu "Cinnamon," and openly prefers his pampered canine existence. He dislikes modern portrayals casting him as foolish or incompetent due to his defeat at Okehazama.

Yoshimoto is married to Marie Antoinette, reincarnated as a female Dachshund, who shares his frustration with inaccurate historical depictions. He notes his wife's hot temper and carefully avoids mentioning his past romantic relationships to prevent conflicts. His interactions with other reincarnated warlords remain generally amicable, reflecting the theme of former rivals finding peace in their new lives.