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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Takeda Nobuyoshi
Takeda Nobuyoshi (1128–1186 or later) was a prominent Japanese samurai lord of the late Heian and early Kamakura periods and the founder of the Takeda clan.
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Tokugawa Iemochi
Tokugawa Iemochi (1846–1866) was the fourteenth shōgun of the Tokugawa shogunate and ruled from 1858 until his death. His reign came during the turbulent final years of the shogunate, when Japan faced growing Western pressure and serious internal political conflict.
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Tokugawa Ienari
Tokugawa Ienari (1773–1841) was the eleventh shōgun of the Tokugawa shogunate and ruled from 1787 to 1837, making him the longest-serving Tokugawa shōgun. He was a great-grandson of the eighth shōgun, Tokugawa Yoshimune.
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Matsudaira Nobuyasu
Matsudaira Nobuyasu was only twenty years old when his father ordered him to commit seppuku. The reason was not a defeat in battle, but a crisis inside the Tokugawa family that had become too dangerous to ignore.
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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.
