Asai Nagamasa inherited power from his father, Asai Hisamasa, when he was only fifteen years old. Both brave and impulsive, he proved himself a capable commander, managing to regain lands from the Rokkaku clan that had previously been lost by his father. After a territorial dispute with Oda Nobunaga over the province of Mino, Nagamasa formed an alliance with Nobunaga and married his sister Oichi, who was famous for her beauty. In 1570, when Oda Nobunaga declared war on the Asakura family, Nagamasa sided with the Asakura because he had long-standing ties with them. This unexpected move threatened Nobunaga's invasion of the Asakura lands by threatening him from the rear. Oda managed to save his army, not without the help of Tokugawa Ieyasu, but relations between Nobunaga and Asai were permanently damaged.
In the summer of that year, the combined forces of Oda and Tokugawa marched against the armies of Asai and Asakura. Asai's army was a formidable force. It is believed that together with his vassals — Isono, Atsuji, Shinzō, Akao, Amemori, and Imai, he could field about ten thousand men, a significant portion of whom were armed with arquebuses. Asai and Asakura attached great importance to this weapon and established one of the three main centers of rifle production in Japan in Kunimoto, located in the province of Omi.
Despite all the preparations and armaments, in the bloody battle of Anegawa, the troops of Asai Nagamasa and Asakura Yoshikage were defeated and forced to flee. After that, Nagamasa finally became part of the anti-Nobunaga alliance, which also included the Asakura, Rokkaku, and the monks of Enryaku-ji Temple. This alliance was secretly supported by Shogun Ashikaga Yoshiaki, who was under the control of Oda Nobunaga.
In 1573, after the death of Takeda Shingen, Oda Nobunaga won a decisive victory over the Asakura army and laid siege to Odani Castle, which served as Nagamasa's residence. Finding himself under siege and with no hope of rescue, Nagamasa sent his wife Oichi and their three daughters to Nobunaga, after which he committed suicide.
Interestingly, one of Asai Nagamasa's daughters, Yodogimi, also famous for her beauty, became a concubine of Toyotomi Hideyoshi and bore him a son named Hideyori. This son died after the fall of Osaka Castle, which was taken by Tokugawa Ieyasu in 1615. Ironically, another daughter of Nagamasa married Ieyasu's son, Hidetada, and became the mother of the third shogun of the Tokugawa family, Iemitsu.
See also
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Yamagata Masakage
Masakage was one of Takeda Shingen’s most loyal and capable commanders. He was included in the famous list of the “Twenty-Four Generals of Takeda Shingen” and also belonged to the inner circle of four especially trusted warlords known as the Shitennō.
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Yagyu Munenori
Yagyū Munenori began his service under Tokugawa Ieyasu while his father, Yagyū Muneyoshi, was still at his side. In 1600, Munenori took part in the decisive Battle of Sekigahara. As early as 1601, he was appointed a kenjutsu instructor to Tokugawa Hidetada, Ieyasu’s son, who later became the second shogun of the Tokugawa clan.
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Yagyu Muneyoshi
A samurai from Yamato Province, he was born into a family that had been defeated in its struggle against the Tsutsui clan. Muneyoshi first took part in battle at the age of sixteen. Due to circumstances beyond his control, he was forced to enter the service of the Tsutsui house and later served Miyoshi Tōkei. He subsequently came under the command of Matsunaga Hisahide and in time became a vassal first of Oda and later of Toyotomi.
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Endo Naozune
Naozune served under Azai Nagamasa and was one of the clan’s leading vassals, renowned for his bravery and determination. He accompanied Nagamasa during his first meeting with Oda Nobunaga and at that time asked for permission to kill Nobunaga, fearing him as an extremely dangerous man; however, Nagamasa did not grant this request.
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Hosokawa Sumimoto
Sumimoto came from the Hosokawa clan: he was the biological son of Hosokawa Yoshiharu and at the same time the adopted son of Hosokawa Masamoto, the heir of Hosokawa Katsumoto, one of the principal instigators of the Ōnin War. Masamoto was homosexual, never married, and had no children of his own. At first he adopted Sumiyuki, a scion of the aristocratic Kujō family, but this choice provoked dissatisfaction and sharp criticism from the senior vassals of the Hosokawa house. As a result, Masamoto changed his decision and proclaimed Sumimoto as his heir, a representative of a collateral branch of the Hosokawa clan that had long been based in Awa Province on the island of Shikoku. Almost immediately after this, the boy became entangled in a complex and bitter web of political intrigue.
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Honda Masanobu
Masanobu initially belonged to the retinue of Tokugawa Ieyasu, but later entered the service of Sakai Shōgen, a daimyo and priest from Ueno. This shift automatically made him an enemy of Ieyasu, who was engaged in conflict with the Ikkō-ikki movement in Mikawa Province. After the Ikkō-ikki were defeated in 1564, Masanobu was forced to flee, but in time he returned and once again entered Ieyasu’s service. He did not gain fame as a military commander due to a wound sustained in his youth; nevertheless, over the following fifty years he consistently remained loyal to Ieyasu.
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Honda Masazumi
Masazumi was the eldest son of Honda Masanobu. From a young age, he served Tokugawa Ieyasu alongside his father, taking part in the affairs of the Tokugawa house and gradually gaining experience in both military and administrative matters. At the decisive Battle of Sekigahara in 1600, Masazumi was part of the core Tokugawa forces, a clear sign of the high level of trust Ieyasu placed in him. After the campaign ended, he was given a highly sensitive assignment—serving in the guard of the defeated Ishida Mitsunari, one of Tokugawa’s principal enemies—an obligation that required exceptional reliability and caution.
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Hojo Shigetoki
Hōjō Shigetoki, the third son of Hōjō Yoshitoki, was still very young—only five years old—when his grandfather Tokimasa became the first member of the Hōjō clan to assume the position of shogunal regent.
