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Ashikaga Yoshimasa, the son of the sixth shogun Ashikaga Yoshinori, was originally known as Miharu in his childhood. His official wife was Hino Tomiko.

On August 16, 1443, the 10-year-old shogun Yoshikatsu tragically passed away due to injuries sustained in a fall from a horse. He had held the position for only three years. In response, the bakufu promptly appointed Yoshikatsu's even younger brother, Yoshinari, as the new shogun. After a few years, Yoshinari changed his name to Yoshimasa, a name by which he is better known.

By 1464, Yoshimasa faced a succession challenge as he had no heir. To preempt any conflicts that might arise at the end of his shogunate, he adopted his younger brother, Ashikaga Yoshimi. However, the following year brought an unexpected development: the birth of a son, Ashikaga Yoshihisa. This event ignited a dispute between the two brothers over who would succeed Yoshimasa as shogun. Yoshimasa's wife, Hino Tomiko, sought support from Yamana Sozen for the infant's claim to the shogunate.

By 1467, this simmering conflict had escalated, causing a division among powerful daimyos and clan factions. The ensuing armed conflict, known as the Onin War, marked the onset of the tumultuous Sengoku period in Japanese history, characterized by prolonged military conflicts spanning over a century.

Amidst the ongoing hostilities, Yoshimasa retired in 1473. He officially passed on the title of Sei-i Taishogun to his young son, who became the ninth shogun Ashikaga Yoshihisa. Nevertheless, Yoshimasa retained significant influence. With the leaders of the warring factions deceased and the ostensible succession dispute settled, the impetus for continued fighting waned. The fatigued armies disbanded, and by 1477, open warfare had ceased.

When Yoshimasa initially declared Yoshihisa as the next shogun upon his own retirement, he expected his son to outlive him. However, Yoshihisa's premature death led Yoshimasa to reassume power and responsibility, which he had intended to relinquish. Subsequently, he adopted his brother Yoshimi's son. In 1489, Yoshitane assumed the position of shogun, and Yoshimasa retired once again.

Before Yoshimasa's passing in 1490, he once more adopted a nephew as his heir, this time the son of his brother Masatomo. While Yoshitane did outlive Yoshimasa, his shogunate proved to be short-lived, ending in 1493.

Prior to marrying Hino Tomiko, who was the sister of Hino Katsumitsu, Yoshimasa had a concubine named Lady Oima. Tragically, when Tomiko pushed Lady Oima down a flight of stairs, she was eight months pregnant, resulting in a miscarriage.

Shogun Yoshimasa's succession saw shogun Yoshihisa (his natural son), followed by shogun Yoshitane (his first adopted son), and then shogun Yoshizumi (his second adopted son). Yoshizumi's descendants would directly follow him as leaders of the shogunate. Additionally, external power struggles within the clan would later result in a brief period during which Yoshitane's great-grandson would be installed as a figurehead leader of the Ashikaga shogunate.

The reign of Yoshimasa witnessed the flourishing of Higashiyama culture, renowned for its contributions to the tea ceremony (Sado), flower arrangement (Kado or Ikebana), Noh drama, and Indian ink painting. This cultural movement was profoundly influenced by Zen Buddhism and saw the emergence of Japanese aesthetic principles like Wabi-sabi, along with the integration of imperial court (Kuge) and samurai (Bushi) culture.


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