Ii Naomasa, recognized as one of the Four Guardians of the Tokugawa clan alongside generals Honda Tadakatsu, Sakakibara Yasumasa, and Sakai Tadatsugu, hailed from Hoda Village in Totomi Province (present-day western Shizuoka Prefecture). His family had long served Imagawa Yoshimoto until Yoshimoto's demise at the Battle of Okehazama.
Born to Ii Naochika, Naomasa faced familial upheaval when his father was unjustly accused of treason, leading to his exile and subsequent execution by Yoshimoto's son, Ujizane, in January of 1563. At the tender age of three, Naomasa, orphaned by this tragedy, was taken in by the Tokugawa family. Following the death of his stepmother, Naotora, in September of 1582, he assumed leadership of the Ii clan.
Commencing his service to the Tokugawa in the mid-1570s, Naomasa earned Tokugawa Ieyasu's high regard and was rewarded with a fief in Omi (Shiga Prefecture). Notably, at the Battle of Nagakute in 1584, he commanded 3,000 matchlock gunners and secured victory against Ikeda Tsuneoki's forces, earning commendation from the opposing leader, Toyotomi Hideyoshi. After this battle, Hideyoshi's mother was placed under Naomasa's care as a hostage to solidify the Toyotomi-Tokugawa alliance.
During the 1590 siege of Odawara, Naomasa played a pivotal role in breaching the castle walls, leading to the surrender of the Hojo clan. His efforts earned him Minowa Castle in Takasaki, Gunma, making him the largest landholder among Tokugawa retainers.
In 1600, at the Battle of Sekigahara, Naomasa and his son-in-law, Matsudaira Tadayoshi, initiated a daring attack on the Western allied Ukita troops, despite not being the first into battle as initially designated. Although surviving the intense seven-hour conflict, Naomasa sustained severe injuries in the final moments while pursuing the escaping Shimazu clan. Despite personal care from Ieyasu, the wounds from Sekigahara are believed to have contributed to Naomasa's premature death two years later.
In recognition of his valor, Naomasa was granted lands in modern-day Hikone. Disliking Ishida Mitsunari, the former owner of the area, to such an extent that he refused to live in his shadow, Naomasa had Ishida's castle on Sawayama demolished and significant topsoil removed from the mountain. Intent on establishing a new castle on Mt Hikone, he began construction but passed away before its completion.
See also
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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.
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Ban Naoyuki
He was also known as Ban Danemon. In the early stages of his military career, he served under Kato Yoshiaki, one of the so-called “Seven Spears of Shizugatake,” who later became the ruler of the Aizu region in Mutsu Province. Naoyuki held the position of commander of the arquebusiers (teppo taishō).
