Lifespan: Hōtoku 3 (1451) to 6/26 of Eishō 4 (1507)
Lord: Hosokawa Masamoto
Father: Akazawa Tsunetaka
Siblings: Tomotsune, Tsunekata, Yukiyoshi, Yoshitsune
Children: Masatsune, Nagatsune (adopted)
Akazawa Tomotsune served as a bushō during the early Sengoku period. The Akazawa were a branch of the Ogasawara clan of Shinano Province.
The Akazawa were based at Shiozaki Castle in Shinano. Tomotsune assigned control of the clan to his eldest son, Akazawa Masatsune, and moved to Kyōto. The main branch of the Ogasawara clan had earlier initiated Hosokawa Masamoto, the kanrei, or deputy shōgun of the Muromachi bakufu, to the Ogasawara school of traditional arts including archery, equestrian arts, and manners of etiquette such as the tea ceremony. Through his connection to the Ogasawara, Tomotsune became an instructor to Ashikaga Yoshimasa, the eighth shōgun, in archery while, at the same time, managing security in Kyōto. Tomotsune further leveraged the prior affiliation that his family had in support of Masamoto.
In 1491, Tomotsune participated in the second chapter of a two-part campaign aimed at eliminating Rokkaku Yukitaka (later known as Takayori) of Ōmi Province known as the Chōkyō-Entoku Expedition. The event, which failed in its purposes, was led by Ashikaga Yoshitane, the tenth shōgun. Impressed by Tomotsune’s skill at falconry, Masamoto had him serve as one of his officials. As a member of a group of tozama, or daimyō from outside the clan, Tomotsune fought in a series of battles in Yamashiro, Kawachi, and Yamato provinces. Tomotsune was appointed the deputy military governor of the Kuse, Tsuzuki, and Sōraku districts of southern Yamashiro, the official in charge of seventeen locations in Kawachi for the collection of rice duties for the bakufu, the daikan, or governor for eight territories held by the Myōhō Temple in Kawachi, and governor for the mountainous lands in Gokashō held by the Konoe family.
In the seventh month of 1499, Masamoto ordered Tomotsune and Hōkabe Munekazu to burn down the Enryaku Temple on Mount Hiei to retaliate against the monks for their support of Ashikaga Yoshitane. On 7/11, Tomotsune participated in a full-scale attack against the temple facilities on Mount Hiei, burning down all of the principal structures, including the main temple hall, lecture halls, meditation halls, scripture houses, the bell tower, and monasteries on the mountain. In the ninth month, Tomotsune rushed to the southern portion of Yamashiro Province and captured Mimaki, Kako, and Makishima castles. This created a line of defense against kokujin from Yamato Province, including Tsutsui Junken and Tōichi Tōharu, who supported a campaign by Hatakeyama Hisanobu in Kawachi on behalf of Yoshitane. In the twelfth month, the army forced its way from Yamashiro into Yamato in pursuit of the kokujin from Yamato, burning down along the way the Kikō, Hokke, Saidai, and Kakuan temples. The men occupied the northern portion of Yamato and seized the territory of the kokujin who had been allied with Hisanobu.
In 1500, Tomotsune and the accompanying forces reinforced their control over northern Yamato, defeating Hisanobu in the ninth month and launching repeated military operations. In 1501, Tomotsune sent a letter to Ogasawara Sadamoto requesting that he dispatch reinforcements in support of Shiba Yoshihiro, the military governor of Owari Province, who was under pressure from Imagawa Ujichika.
In response to the advancing forces, in the second month of 1501, the monks at the Kōfuku Temple moved sacred objects and the invaders were requested by the Imperial Court to withdraw from the area, but the army continued to deploy in Yamato into 1502. That same year, Iba Sadataka (the deputy military governor of Ōmi and supporter of Yoshizumi) rebelled after being cornered by Rokkaku Takayori (the military governor of Ōmi aligned with Yoshitane). In the third month of 1503, Tomotsune deployed to Ōmi and, together with Sadataka, attacked Otowa Castle held by the Gamō where Takayori was holed up. In the sixth month, Sadataka and Takaori reconciled through the mediation of Masamoto who had returned to the capital. The confrontation between Sadataka and Takayori is known as the Conflict of the Iba Clan.
In the third month of 1504, Tomotsune rebelled against Masamoto, but was pardoned months later through the mediation of Yakushiji Motokazu and went to Kyōto. Months later, Tomotsune conspired with Motokazu to depose of their lord, Masamoto, in lieu of Masamoto’s adopted son, Hosokawa Sumimoto. This plan was interrupted by Motokazu’s younger brother, Yakushiji Nagatada, leading to the arrest of Motokazu and Tomotsune. Masamoto, however, respected Tomotsune’s military prowess so, in 1505, forgave him again, appointing him as the deputy military governor of the Kuse, Tsuzuki, and Sōraki districts of southern Yamashiro. Thereafter, Tomotsune served as a retainer of Masamoto.
In the first month of 1506, he defeated Hatakeyama Yoshihide and Hatakeyama Hisanobu, capturing Takaya Castle. He then invaded Yamato again, and aimed to suppress support from the temples and shrines by torching, among others, the Hokke Temple, the Shōryaku Temple on Mount Bodai, the Tanzan Shrine on the Tōno Ridge, and the Ryūmon Temple. He joined Miyoshi Yukinaga to expand the Hosokawa domain by engaging in battles across the Kinai Region.
In 1507, upon orders from Masamoto, Tomotsune attacked Isshiki Yoshiari in Tango Province. At the height of the battle, on 6/23, he learned that Masamoto had been assassinated by Yakushiji Nagatada, Kōzai Motonaga, and Takeda Magoshichi in an event known as the Eishō Disturbance (Eishō no sakuran). While attempting to withdraw the army to Kyōto, he incurred a counterattack by Yoshiari, Ishikawa Naotsune, and other kokujin from Tango. On 6/26, he killed himself in a hall housing the Monju Bodhissatva in Kusenoto in Tango. Awaya Chikahide and Furuichi Tanemori from Wakasa Province also died at this time. Tomotsune’s adopted son, Nagatsune, survived to later serve Sumimoto.