
Ōuchi Yoshihiro was the second son of Ōuchi Hiroyo, who headed the Ōuchi clan in the western part of Honshu. In 1363, Shogun Ashikaga Yoshimitsu confirmed the Ōuchi family in the position of shugo of Suō and Nagato Provinces. In his youth, Yoshihiro assisted his father in strengthening the influence of the Northern Court on the island of Kyushu — they served under Imagawa Ryōsun, who had been tasked with subjugating the nine provinces of Kyushu.
After Hiroyo’s death in 1379, Yoshihiro became involved in a conflict with his elder brother. As early as 1380, he defeated his brother’s forces at the Battle of Sakariyama and assumed leadership of the Ōuchi clan. In 1391, Yoshihiro led his army into the regions surrounding the capital, supporting Shogun Yoshimitsu in delivering the final blow to the remaining forces of the Southern Court. For this assistance, he was granted two more provinces. However, Yoshihiro rendered his most valuable service to the Ashikaga in 1392, when he persuaded the emperor of the Southern Court to accept the Ashikaga proposal of alternating succession between the senior and junior imperial lines — a compromise that brought an end to the nearly sixty-year-long War of the Northern and Southern Courts.
In the years following his father’s death, Yoshihiro’s influence grew significantly — both among the feudal lords of western Japan and among the pirates of the Inland Sea, with whom he shared not only the spoils of their raids on China and Korea but also the profits from trade with those countries, which flourished during Yoshimitsu’s rule.
Over time, however, relations between Ōuchi Yoshihiro and Ashikaga Yoshimitsu deteriorated. Yoshimitsu demanded that Yoshihiro build him a residence in Kitayama, a demand that Yoshihiro saw as unprecedented and insulting. In 1399, Yoshihiro rebelled and marched his forces toward the capital region. His rear was secured by the powerful Ōtomo clan, which held the position of shugo over three provinces in Kyushu.
As he advanced westward, Yoshihiro discovered that the lords of Suō, Nagato, Aki, and Bizen were ready to support his uprising. He also managed to gain the favor of the Kantō Kanrei, Ashikaga Mitsukane, and expected to strengthen his army with discontented warriors from the capital provinces.
Nevertheless, lacking accurate information about the shogunate’s troop strength, Yoshihiro chose not to attack Kyoto. Instead, he fortified himself in the coastal city of Sakai, which by that time had already become a major commercial center with a degree of autonomy. This occurred in late autumn of 1399. Preparing for the siege, Yoshihiro surrounded the city with watchtowers (yagura) and ordered wells dug to secure a water supply. From the seaside, he expected aid from pirates, who were supposed to deliver food and maintain communication with Yoshihiro’s allies on Shikoku Island and in Kii Province.
Ashikaga Yoshimitsu attempted to resolve the conflict peacefully by sending the Buddhist monk Zekkai to negotiate. However, Yoshihiro firmly refused to surrender, and Zekkai returned empty-handed. Yoshimitsu then gathered the troops of his most powerful allies — the Hatakeyama, Hosokawa, and Chiba (Shiba) clans — and laid siege to Sakai. Yoshihiro hoped that with pirate support he could break the blockade, but Yoshimitsu succeeded in bribing the pirates over to his side. Unfortunately for Yoshihiro, the forces he had raised in Iwami and Izumi Provinces proved poorly trained and unreliable. Furthermore, Ashikaga Mitsukane betrayed him and failed to send the promised Kantō troops.
Surrounded by land and sea, Yoshihiro became trapped. The fortifications he had built in Sakai were strong, and for several weeks the fighting brought no decisive advantage to either side. But in the middle of the twelfth month of 1399, taking advantage of a strong north wind, the bakufu troops managed to set the city on fire. The blaze destroyed most of the merchant districts and the warehouses filled with goods. Soon the flames reached Yoshihiro’s stronghold in central Sakai, after which the shogunate’s forces launched an assault. Seeing no way to escape, Yoshihiro took his own life.
See also
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Ouchi Yoshioki

Ouchi Yoshioki, the ruler of the provinces of Suo, Nagato, and Iwami, was one of the most capable military commanders and politicians of the late 15th and early 16th centuries. The son of Ouchi Masahiro, he governed from his residence in Yamaguchi in the province of Suo. In 1499, Yoshioki gave refuge to Shogun Ashikaga Yoshitane, who had been driven out of Kyoto by Hosokawa Masamoto. Shogun Yoshizumi, Masamoto’s protégé, ordered the lords of Kyushu to unite their forces against Yoshioki; however, they did not dare to do so, fearing the power of a man who by that time controlled six provinces. Having gathered a substantial army, Yoshioki marched from his native Suo toward Kyoto in order to restore Shogun Yoshitane to power.
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Otomo Sorin

Ōtomo Yoshishige came from a noble lineage, being the eldest son of Ōtomo Yoshiaki, the ruler of Funai Province. The roots of the Ōtomo family traced back to Fujiwara Hidesato, the adopted son of Nakahara Chikayoshi. Fujiwara served Minamoto Yoritomo during the Genpei War and took part in battles in Mutsu Province in 1189. In 1193, he was appointed shugo of Buzen and Bungo Provinces, after which he adopted a new surname—Ōtomo.
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Okudaira Sadamasa

Sadamasa was the son of Okudaira Sadayoshi and took part in several battles under Tokugawa Ieyasu, distinguishing himself in the Battle of Anegawa in 1570, where he took two heads. Around 1572 he was forced to enter the service of the Takeda clan, but after the death of Takeda Shingen in 1573 he returned to Tokugawa, leaving Tsukude Castle together with his men. As a result of this defection, Takeda Katsuyori ordered the execution of Sadamasa’s wife and brother, who were being held as hostages.
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Okubo Tadatika

Tadatika, the son of Okubo Tadayō, entered the service of Tokugawa Ieyasu at the age of eleven, and took his first head in battle when he was sixteen. After the establishment of the Tokugawa shogunate, he was appointed as a rōjū — a senior bakufu official — and was regarded as one of Ieyasu’s most trusted advisors, alongside Honda Masanobu. He is also known for his military chronicle Mikawa Monogatari, which describes Ieyasu’s rise to power and the early years of the Tokugawa shogunate.
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Okubo Nagayasu

Nagayasu was the second son of Okura Nobuyasu, a sarugaku theater actor from the Takeda clan. Takeda Shingen recognized the young man’s potential and took him into service, appointing him as a vassal to his general, Tsuchiya Masatsugu. During this period, Nagayasu changed his family name to Tsuchiya. He was entrusted with developing the Takeda clan’s gold mines as well as handling matters related to taxation.
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Nitta Yoshisada

Nitta Yoshisada was a loyal soldier of Emperor Go-Daigo, who in the 1330s attempted to restore direct imperial rule in Japan. The Nitta family was related to the Ashikaga house and was older in lineage. However, they did not join Minamoto Yoritomo at the start of his war with the Taira, as the Ashikaga did, and therefore did not receive high positions in the Kamakura shogunate. This may have been one of the reasons why Yoshisada rose against the Hōjō clan in 1333.
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Natsume Yoshinobu

Yoshinobu, a long-time vassal of the Matsudaira and Tokugawa clans, governed Hamamatsu Castle on behalf of the Tokugawa house. During the clashes between the Imagawa, Takeda, and Matsudaira clans, he served in the garrison of Nagasawa Castle and in 1562 took part in raids under the command of Itakura Shigezane. When, in 1563, a revolt of the Sōtō-shū sect followers broke out in Mikawa Province, Yoshinobu joined the rebels together with Honda Masanobu and Hachiya Sadatsugu.
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Nambu Nobunao

The Nambu clan was an ancient and powerful family that traced its lineage back to the Minamoto shoguns and had controlled a significant part of the Tohoku region in northern Honshu since the 12th century. Nobunao was born in Ikatai Castle, located in what is now the city of Iwate. He was the second son of Ishikawa (Nambu) Takanobu, the 22nd head of the Nambu clan. In 1565, Nobunao’s uncle, Nambu Harumasa, adopted him, brought him to Sannohe Castle, and named him his heir, later giving his daughter in marriage to him.
