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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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.
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Araki Murashige
Araki Murashige (1535 – June 20, 1586) was a samurai and retainer of Ikeda Katsumasa, the head of the powerful Settsu-Ikeda clan in Settsu Province. Initially serving under Katsumasa, he aligned himself with Oda Nobunaga after Nobunaga’s successful campaign to establish control over Kyoto.
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Yuki Hideyasu
Yuki Hideyasu (March 1, 1574 – June 2, 1607) was a Japanese samurai who lived during the Azuchi–Momoyama and early Edo periods, serving as the daimyō of Fukui Domain in Echizen Province. Born Tokugawa Ogimaru, he was the second son of Tokugawa Ieyasu and Lady Oman (also known as Lady Kogō), a handmaiden to Ieyasu’s wife, Lady Tsukiyama. Due to Ieyasu’s fears of his wife’s reaction to Oman’s pregnancy, Ogimaru and his twin brother were born in secrecy at the home of Honda Shigetsugu, one of Ieyasu’s retainers. Oman’s other son eventually became a priest, while Ogimaru was raised apart from Ieyasu, whom he only met at the age of three, in a meeting arranged by his older half-brother, Matsudaira Nobuyasu.
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Tsutsui Sadatsugu
Tsutsui Sadatsugu (June 6, 1562 – April 2, 1615) was a prominent figure in the Sengoku and early Edo periods, known as the cousin and adopted heir of Tsutsui Junkei, the feudal lord of Yamato Province. Following Junkei's death in 1584, Toyotomi Hideyoshi relocated Sadatsugu to Iga Province, where he oversaw the construction of Iga Ueno Castle, marking the height of his prominence.
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Matsudaira Kiyoyasu
Matsudaira Kiyoyasu (September 28, 1511 – November 29, 1535) served as the 7th lord of the Matsudaira clan during Japan's tumultuous Sengoku period. Renowned as the paternal grandfather of Tokugawa Ieyasu, one of Japan's "great unifiers," Kiyoyasu expanded his clan’s influence, bringing all of northern Mikawa Province under his control after subduing the Saigo clan. His power was further symbolized by the construction of Okazaki Castle, a testament to the Matsudaira’s growing dominance.
