From the very beginning of his career, Takatsugu served under Oda Nobunaga and was married to Nobunaga’s niece, which secured him a strong position at court and close ties to one of the most powerful clans of the era. However, the events of 1582 drastically changed his fate. When Akechi Mitsuhide rebelled against Nobunaga and treacherously killed him at the Honnō-ji Temple, Takatsugu sought to take advantage of the ensuing chaos to strengthen his own standing. He launched an attack on Nagahama Castle in Ōmi Province, hoping to expand his territories. The assault, however, was repelled, and soon after, Mitsuhide was defeated by Toyotomi Hideyoshi’s forces at the Battle of Yamazaki, leaving Takatsugu without allies or support.
Finding himself in a precarious situation, Takatsugu turned to Hori Hidemasa, a renowned general who helped arrange his service under Shibata Katsuie — one of the most powerful warlords of the time and a staunch rival of Hideyoshi. Yet in the following year, 1583, Katsuie’s army was decisively defeated by Hideyoshi’s forces at the Battle of Shizugatake, and Katsuie, realizing his defeat, took his own life through seppuku. Anticipating the collapse of his lord’s cause, Takatsugu fled to the domains of his relative Takeda Motoaki, who was married to Takatsugu’s sister. Fate, however, once again turned against him — soon Motoaki was executed on Hideyoshi’s orders as part of his campaign to eliminate potential threats to his rule.
Remarkably, Takatsugu avoided his relative’s grim fate. Not only was he spared punishment, but he was also granted a landholding — a clear sign that Hideyoshi saw value in Takatsugu’s abilities and connections. His sister was sent to Osaka as one of Hideyoshi’s concubines, and it was likely through this familial link that Takatsugu gradually rose to favor with the new ruler. His income increased steadily: first to 2,500 koku of rice, then to 10,000, later to 28,000, and eventually reaching an impressive 60,000 koku per year. Along with this rise in wealth, Takatsugu received control over Ōtsu Castle in Ōmi Province, establishing himself as a powerful feudal lord with his own administrative and military authority.
In 1590, Takatsugu took part in Hideyoshi’s campaign against the Hōjō clan — the famous Odawara campaign — which resulted in Hideyoshi consolidating control over Japan’s eastern provinces. His contributions to this campaign further solidified his standing among Toyotomi’s vassals. Yet after Hideyoshi’s death, Japan’s political landscape shifted once again. In 1600, during the decisive Sekigahara campaign — the great struggle between Tokugawa Ieyasu’s Eastern Army and the Western Coalition loyal to the Toyotomi heirs — Takatsugu made a calculated decision to side with Tokugawa.
This decision brought its own trials. Ōtsu Castle, under Takatsugu’s command, was besieged by a Western Coalition force numbering around fifteen thousand men. Despite being vastly outnumbered, Takatsugu displayed resilience and tactical skill in defending the fortress. His garrison held out for nine days, repelling repeated assaults, and only on October 21 — the very day that the main Battle of Sekigahara ended in Tokugawa’s decisive victory — did Takatsugu surrender the castle. Respecting his bravery and the honor befitting a samurai, the Western generals permitted him to shave his head and retire to a monastery on Mount Kōya, where he found temporary refuge.
After Tokugawa Ieyasu’s ultimate triumph, he deeply appreciated Takatsugu’s contribution to the campaign. Although Takatsugu had technically surrendered, his defense of Ōtsu had delayed a significant portion of the Western forces, indirectly aiding Tokugawa’s victory on the main battlefield. In recognition of his loyalty and service, Ieyasu rewarded him generously with new lands in Wakasa Province, providing an annual income of 92,000 koku of rice. This gift symbolized Ieyasu’s trust and acknowledgment of Takatsugu’s courage and wisdom. Kyōgoku Takatsugu thus entered history as an example of a samurai who not only survived but also thrived during one of the most turbulent transitions in Japanese history — the shift from the Sengoku era to the Edo period.
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.
