Lifespan: Tenbun 17 (1548) to Genna 1 (1615) or Genna 9 (1623)
Other Names: Genta, Kagekuni
Title: Junior Fifth Rank (Lower) and Governor of Mino
Lord: Ashikaga Yoshiuji → Satake Yoshishige → Satake Yoshinobu → Yūki Hideyasu → Matsudaira Tadanao
Father: Ōta Sukemasa
Mother: Daughter of Ōishi Sadahisa
Siblings: Ōta Ujisuke, Masakage, Ōta Suketake (Ōta Kagesuke), Ushioda Suketada, sister (wife of Narita Ujinaga), sister (wife of Tagaya Shigetsune)
Wife: Daughter of Makabe Hisamoto
Adopted Children: Kageyoshi (natural son of Ōta Suketake)
Kajiwara Masakage served as a bushō from the Sengoku to early Edo periods.
Masakage was born as the second son of Ōta Sukemasa of the Iwatsuki-Ōta clan of Musashi Province. He was the younger brother of a different mother of Ōta Ujisuke who served as a retainer of the Hōjō.
Masakage was adopted by the widow of Kajiwara Kōzuke-no-suke and took the surname of Kajiwara. There are various theories regarding the timing of the adoption of this name. He was born in 1548, and, in the third month of 1557, attended his coming-of-age ceremony in the presence of Ashikaga Yoshiuji at Kasai Castle during which he was called Kajiwara Genta Masakage. The Kajiwara clan appear as members of the hōkōshū, the military organ under the direct control of the family of the Koga kubō. During the Eishō era (1504 to 1521), there was an individual named Kajiwara Saburō Masakage so there is a strong likelihood that he inherited the name. Moreover, the name of Kajiwara Genta was used by a bushō from the Kamakura period named Kajiwara Kagesue, but the connection between the Kajiwara clan of the Kamakura period and the Kajiwara clan who served as members of the military organ of the Koga kubō is unclear. Soon after the coming-of-age ceremony, Masakage’s name appears in the role of a sōshaban, or intermediary for visits or the exchange of messages or gifts with regional daimyō, so he appears to have served as an attendant of Yoshiuji.
In 1560, after his father acted in concert with Uesugi Kenshin to back Ashikaga Fujiuji as the Koga kubō, Masakage left Yoshiuji and returned to Iwatsuki Castle in the Saitama District of Musashi.
The break in relations between the Ōta and the Hōjō, along with the return of Masakage to Musashi, left his older brother, Ōta Ujisuke, in a delicate position after having wed the daughter of Hōjō Ujiyasu. Finally, in 1564, Sukemasa was ousted by his son, Ujisuke, while Masakage was incarcerated. Later, through the devices of his retainers, Masakage was able to flee. He first received assistance from Utsunomiya Hirotsuna with whom Sukemasa was temporarily staying and then, together with his father, turned to Satake Yoshishige, the eighteenth head of the Satake clan in Hitachi Province, becoming his retainers. Meanwhile, his mother from the Ōishi clan who had earlier been sent by Ujisuke as a hostage to Odawara Castle was rescued, upon orders of Masakage, through the desperate efforts of his retainers and sent back to Masakage.
During the campaign of Satake Yoshishige to eliminate Oda Ujiharu, Masakage defeated Ujiharu’s forces and, in recognition of his contributions, was awarded Oda Castle. In 1577, he responded to an attack by Hōjō Ujinao (Ujinao’s first experience in battle) and engaged in a series of contests against the Hōjō. Masakage continued his operations to oppose the Hōjō, including coordination with Satomi Yoshiyori (a sengoku daimyō of Awa Province) and Tokugawa Ieyasu (who held territory in Mikawa, Tōtōmi, and Suruga provinces) to plan a pincer attack against them.
In 1584, at the height of the Battle of Numajiri, Masakage suddenly betrayed the allied forces of the Satake and Utsunomiya by colluding with the Hōjō. The battle ended in a draw, and, through the intervention of his father, Sukemasa, he later returned to the service of the Satake. It is surmised that, after the death of Sukemasa, Masakage was not reinstated as his successor as a result of this past incident. In the battle, Masakage’s uncle, Makabe Hisamoto, sided with the Hōjō but, during the extended deployment which ran for over 100 days, he also returned to the service of the Satake.
In 1590, after the Conquest of Odawara, Masakage moved his base upon orders of the Satake clan to Ueda Castle. In 1591, his father, Ōta Sukemasa, died of illness. Later, Masakage deployed for the Bunroku Campaign and crossed to the Korean Peninsula. In 1600, after the Battle of Sekigahara, the Satake clan, owing to their neutral position during the war, were demoted and transferred to Akita in Dewa Province. Masakage initially followed them, but later left to join the Kita-no-shō domain led by Yūki Hideyasu and received a fief of 2,000 koku.
At the Siege of Ōsaka beginning in the winter of 1614, Masakage served as a retainer of Matsudaira Tadanao (the son of Yūki Hideyasu).
Masakage died in 1615. Under an alternate theory, he died in 1623. He did not appear to have children so the headship of the Ōta clan was inherited by his younger brother, Ōta Suketake. Suketake’s son, Kajiwara Kageyoshi, inherited the headship of the Kajiwara clan and served Tokugawa Tadanaga.
His grave is at the Zenrin Temple in Fukui.