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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Kato Yoshiaki
Yoshiaki, a loyal vassal of the Oda clan, first distinguished himself as a talented warrior during the Battle of Shizugatake in 1583. For his bravery and outstanding military achievements, he was included in the famous group known as the “Seven Spears of Shizugatake” — an elite band of samurai celebrated for their exceptional courage in that battle. Later, Yoshiaki became one of Toyotomi Hideyoshi’s naval admirals and took an active part in his subsequent military campaigns. He commanded warships during the expeditions to Kyushu and the siege of Odawara, demonstrating not only valor but also exceptional leadership and strategic skill. For his loyal service and effective command, Yoshiaki was granted an estate in Matsuzaki with an annual income of 100,000 koku of rice — a symbol of significant rank and prosperity.
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Katagiri Katsumoto
Katsumoto was born into the family of Katagiri Naomasa, who came from an ancient and noble lineage. The Katagiri clan had served the early shoguns of the Minamoto house for over five centuries and held lands in the northern part of Shinano Province.
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Kasuya Takenori
There are several versions regarding the origins of Takenori. According to one account, he was the second son of Kasuya Tadayasu, a samurai who served the Bessho clan in Harima Province. In 1577, when Toyotomi Hideyoshi launched his campaign in Harima, on the advice of his close retainer Kuroda Yoshitaka, also known as Kanbei, he took Takenori into his service as a page. In this position, the young warrior participated in the siege of Miki Castle, which lasted from 1578 to 1580 and was aimed at suppressing the rebellion led by Bessho Nagaharu.
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Kajiwara Kagetoki
One of the finest generals and most loyal allies of Minamoto no Yoritomo, Kagetoki gained a notorious reputation as a jealous rival and persecutor of Yoshitsune, the legendary commander of the Genpei War. Kagetoki was an intelligent, calculating, and cautious man.
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Kawakubo (Takeda) Nobuzane
Nobuzane was the seventh son of Takeda Nobutora and the half-brother of the famous Takeda Shingen. The identity of his mother is unknown, as is the exact year of his birth. It is believed that he was born sometime in the 1530s. When Nobuzane reached adulthood, he was sent to the village of Kawakubo, located in the northern part of Kai Province near the border with the Saku region. His duty was to guard the road leading north. In that village, he built a residence and changed his family name to Kawakubo.
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Imagawa Sadayo
Imagawa Sadayo was one of the most outstanding figures of his era. Alongside Kusunoki Masashige and Kitabatake Chikafusa, he was considered one of the greatest generals and strategists of his time. In addition to his military talents, Sadayo was also a poet and historian, and his literary abilities earned him a prominent place at court and in scholarly circles.
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Ikeda Motosuke
Motosuke was the son of Ikeda Tsunooki and the older brother of the famous military commander Ikeda Terumasa. Sources differ on his year of birth—it was either 1559 or 1564. Motosuke was married to the sister of Oda Nobutada, the eldest son of Oda Nobunaga. Thus, Nobutada's son, Oda Hidenobu, was his nephew.
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Watanabe (Hanzo) Moritsuna
Moritsuna was the son of Watanabe Takatsuna, a vassal of the Matsudaira clan. He was the same age as Tokugawa Ieyasu and was held hostage with him by the Imagawa clan. In 1557, Moritsuna joined Ieyasu.
