Lifespan: Eishō 6 (1509) to 10/8 of Tenshō 1 (1573)
Rank: Sakai kubō
Title: Junior Fifth Rank (Lower), Chief of the Imperial Cavalry of the Left Division
Bakufu: Muromachi bakufu
Father: Ashikaga Yoshizumi
Mother: From the Shiba clan
Adoptive Father: Ashikaga Yoshitane
Siblings: Yoshiharu, Yoshitsuna
Wife: [Formal] Daughter of Ōuchi Yoshioki
Children: Yoshihide, Yoshisuke, Yoshitō
Ashikaga Yoshitsuna lived during the Sengoku and Azuchi-Momoyama periods. He was the second son of Ashikaga Yoshizumi, the eleventh shōgun of the Muromachi bakufu. Yoshitsuna was adopted by Ashikaga Yoshitane, the tenth shōgun. He was the father of Ashikaga Yoshihide, the fourteenth shōgun, and was referred to as the Sakai kubō or Hirajima kubō.
Yoshitsuna was born in 1509 as the second son of Ashikaga Yoshizumi. He may actually have been the eldest son, but was assigned a lower status than his half-brother, Ashikaga Yoshiharu, owing to differences in the status of their mothers. Yoshiharu was born to Yoshizumi’s formal wife from the Hino family, nobles of the Imperial Court. By contrast, Yoshitsuna’s mother came from the Shiba clan, a cadet family of the Ashikaga of lower status than the Hino. This fact overrode any privilege that ordinarily would arise based on birth order. Yoshitsuna was raised by Hosokawa Yukimochi, the military governor of Awa Province in Shikoku.
In 1527, at the Battle of Katsurakawara, Yoshitsuna joined Miyoshi Motonaga and Hosokawa Harumoto to defeat Hosokawa Takakuni, supporter of Yoshitsuna’s brother, Yoshiharu, the twelfth shōgun. Takakuni was expelled to Ōmi Province. From his base in the city of Sakai in Izumi Province, Yoshitsuna exercised control over the capital of Kyōto, in addition to Yamashiro and Settsu provinces. Yoshitsuna did not formally become the shōgun, but, in the summer of 1527, the Imperial Court conferred upon him the honorary titles of Junior Fifth Rank (Lower), and Chief of the Left Division Imperial Horses. Yoshitsuna was promised he would become the next shōgun so he was called the Sakai kubō, or the shōgun of Sakai.
In 1532, his guardian, Motonaga, was cornered by Hosokawa Harumoto and compelled to commit seppuku. Yoshitsuna then attempted to kill himself but was restrained by Harumoto while the governance of the Sakai kubō collapsed. For a period of five years, Yoshitsuna had been at the center of the bakufu administration. He then went to Awa Province and came under the protection of Hosokawa Yukimochi, the military governor of Awa. In Awa, first he entered the Saikō Temple, and then moved to the Hirashima manor.
In Awa, he received a stipend of 3,000 kan mon. In 1553, Yoshitsuna became upset after an incident in which Miyoshi Jikkyū deliberately killed Hosokawa Mochitaka, the son of Yukimochi. In the fourth month of 1555, Yoshitsuna departed from Awa and came under the protection of the Ōuchi clan of Suō Province. In 1563, he returned to Awa through the intermediation of Miyoshi Nagayasu. Around this time, he developed paralysis. In 1565, Yoshitsuna’s grandson, Ashikaga Yoshiteru, was killed by the Miyoshi Group of Three (Miyoshi sanninshū) in the Eiroku Incident (Eiroku no hen). The Miyoshi Group of Three was comprised of Miyoshi Nagayasu, Miyoshi Sōi, and Iwanari Tomomichi who were active in the Kinai Region to support the governance of the Miyoshi following the death of Miyoshi Nagayoshi. In 1566, Yoshitsuna issued a written instruction to the Miyoshi Group of Three for the elimination of Matsunaga Hisahide.
Later, Yoshitsuna looked after for his eldest son, Ashikaga Yoshihide, who became the fourteenth shōgun with the support of the Miyoshi Group of Three. He prepared in Settsu Province for a final showdown with Ashikaga Yoshiaki who was backed by Oda Nobunaga to become the next shōgun. At the height of this confrontation, Yoshihide died of illness, so Yoshitsuna returned again to Awa Province. He died in 1573.