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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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).
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Asakura Toshikage
The Asakura family, who claimed kinship with several emperors, lived in the province of Echizen. Its representatives were considered hereditary vassals of the Shiba clan. From the mid-15th century until their defeat by Oda Nobunaga's army in 1573, which resulted in the final destruction of the Asakura clan, they were a significant military and economic force.
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Asakura Yoshikage
Yoshikage was the eldest son of Asakura Takakage. He began ruling in 1548 at the age of fifteen, and during his reign he twice defeated the Ikko-ikki forces, in 1555 and 1564. Yoshikage supported the Saito family in their struggle against Oda Nobunaga in 1561–1567. When Ashikaga Yoshiaki fled Kyoto in 1565 after the assassination of his older brother, Shogun Ashikaga Yoshiteru, Yoshikage gave him refuge. However, he was unable to provide sufficient support for Yoshiaki's claim to the title of shogun, and Yoshiaki had to seek help from Oda Nobunaga.
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Asakura Norikage
Norikage came from the ancient samurai clan of Asakura, whose members considered themselves descendants of Prince Kusakabe, son of Emperor Tenmu (631–686). He was the eighth son of daimyo Asakura Takakage and was named Kotaro in childhood. Over time, Asakura Norikage became the pillar of the Asakura clan and was undoubtedly its most talented commander during that difficult period when the clan was experiencing internal difficulties, uprisings by the Ikko-ikki sect, and instability in the lands surrounding the capital. Although Norikage himself was never a daimyo, he served as an advisor to three generations of Asakura clan leaders. He spent his entire life on military campaigns. After his father's death in 1481, Norikage entered the service of his brother, Asakura Ujikage.
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Asai (Azai) Nagamasa
Asai Nagamasa inherited power from his father, Asai Hisamasa, when he was only fifteen years old. Both brave and impulsive, he proved himself a capable commander, managing to regain lands from the Rokkaku clan that had previously been lost by his father. After a territorial dispute with Oda Nobunaga over the province of Mino, Nagamasa formed an alliance with Nobunaga and married his sister Oichi, who was famous for her beauty. In 1570, when Oda Nobunaga declared war on the Asakura family, Nagamasa sided with the Asakura because he had long-standing ties with them. This unexpected move threatened Nobunaga's invasion of the Asakura lands by threatening him from the rear. Oda managed to save his army, not without the help of Tokugawa Ieyasu, but relations between Nobunaga and Asai were permanently damaged.
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Amano Yasukage
Yasukage was born into the family of the samurai Amano Kagetaka and was given the name Matagoro at birth. He later changed his name to Kageyoshi, and then to Yasukage. From an early age, Yasukage served Tokugawa Ieyasu and accompanied him when he was held hostage by Imagawa Yoshimoto. His loyalty and devotion to Ieyasu from a young age laid the foundation for Yasukage's future military and administrative career.
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Amago Tsunekisa
The Amago clan (also spelled Amako) was founded in 1392, when Sasaki Takahisa, who was orphaned at the age of three, took the new surname Amago, meaning “son of a nun,” in honor of the nun who raised him. Since the Sasaki family descended from Emperor Uda (866–931), the Amago clan traced its lineage back to this emperor. From around 1396, the Amago clan's headquarters was the mountain castle of Gassan-Toda in Izumo Province. Until the start of the Onin War, the Amago clan remained a minor clan in the service of the Kyogoku clan, which was also a descendant of the Sasaki clan. The Amago clan historically held the position of vice-governor of Izumo Province.
