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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Oishi Yoshio
Oishi Yoshio (April 24, 1659 – March 20, 1703) served as the chamberlain of the Ako Domain in Harima Province, now part of modern-day Hyogo Prefecture, from 1679 to 1701. He is best known as the leader of the Forty-seven Rōnin in their 1703 vendetta and is honored as the central figure in the legendary tale of Chūshingura.
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Asano Nagaakira
Asano Nagaakira (March 18, 1586 – October 16, 1632) was a Japanese samurai and daimyō of the early Edo period. He initially ruled Wakayama Domain before being transferred to the Hiroshima Domain, where his family would remain until the Meiji Restoration.
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Takigawa Kazumasu
Takigawa Kazumasu (1525 – October 21, 1586), also known as Takikawa Sakon or Sakonshogen, was a prominent samurai and daimyō of the Sengoku period. He served as a loyal retainer and military commander under Oda Nobunaga and later Toyotomi Hideyoshi. His biological son, Toshimasu, was adopted by Maeda Toshihisa, the elder brother of Maeda Toshiie, and Kazumasu served alongside Toshiie in Nobunaga’s campaigns.
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Sanada Yukitaka
Sanada Yukitaka (c. 1512 – June 8, 1574) was a renowned samurai warrior of the Sengoku period, best known as one of the "Twenty-Four Generals of Takeda Shingen." He was the father of Sanada Nobutsuna and Sanada Masayuki, as well as the grandfather of the legendary Sanada Yukimura, who later served the Toyotomi clan.
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Torii Mototada
Torii Mototada (1539 – September 8, 1600) was a Japanese samurai and daimyo who lived through the Sengoku and late Azuchi–Momoyama periods. A loyal retainer of Tokugawa Ieyasu, he is best remembered for his heroic last stand at the Siege of Fushimi, an event that played a crucial role in shaping Japanese history.
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Toyotomi Hideyori
Toyotomi Hideyori (August 28, 1593 – June 4, 1615) was the son and designated successor of Toyotomi Hideyoshi, the general who first unified Japan. His mother, Yodo-dono, was Oda Nobunaga's niece.
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Okubo Tadanori
Okubo Tadanori (January 13, 1842 – August 10, 1897) was the 9th daimyo of Odawara Domain in Sagami Province (modern-day Kanagawa Prefecture) during the late Edo period. Before the Meiji Restoration, he held the courtesy title of Kaga no Kami.
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Okubo Tadayo
Okubo Tadayo (1532 – October 28, 1594) was a samurai general who served Tokugawa Ieyasu during the Azuchi–Momoyama period and later became the daimyo of Odawara Domain in the early Edo period.
