>>92056406Yoshimoto was a very clever nobleman who was good with money and investments as well as politics and alliances. When the power of the Shogun faded due to a massive amount of Clans existing due to every son having a right to an inheritance and a long period of relative peace, he became the secondary power base by acting as Shogun #2 and mediating them.
He was also highly eccentric. His family was descended directly from the family of the second and current Shogunate, the Ashikaga, and he felt entitled to be in on that. He also acted like an early Japanese high noble by blackening his teeth, shaving his eyebrows, wearing classical looking clothes, and using heavy makeup; like a general in the American Civil War walking around woth a snuffbox wearing a powdered wig and breeches. He wanted to restore Japan culturally to the old ways. Also, he was pretty chubby.
He decided he deserved to be Shogun and gathered a huge army then marched on the capital, not knowing everyone and their mother would break their oaths to him (he broke his to the Shogun first, justifying it) and opposed him. He was not a great military leader and was very anxious to become Shogun as a younger man, and suffered nasty attrition before Oda Nobunaga, also gunning to be Shogun, ended his march and killed him.
This showed how frail the Ashikaga rule was, basically beginning the Sengoku era AKA the great samurai clusterfuck.
He set up his Clan well regadless of his failure, and they remained powerful for the rest of Samurai history but never rose up or got involved in major conflict again. Imagawa descendants today are among the industry leaders of Japan.
