Ashikaga Yoshiakira (July 4, 1330 – December 28, 1367) served as the second shogun of the Ashikaga shogunate from 1358 to 1367 during Japan's Muromachi period. He was the son of Ashikaga Takauji, the founder and inaugural shogun of the Muromachi shogunate. His mother, known as Akahashi Toshi or Hojo Nariko, was Takauji's consort.

During his early years, Yoshiakira, then known as Senjuo, resided in Kamakura as a hostage under the guardianship of the Hojo clan. His father, Takauji, aligned himself with the exiled Emperor Go-Daigo, who led a rebellion against the Kamakura shogunate in what is known as the Kenmu Restoration. Yoshiakira actively supported Nitta Yoshisada (1301–1338) in the attack against the Kamakura shogunate. Throughout the Nanboku-cho period, Yoshiakira successfully reclaimed Kyoto from various Loyalist occupations in the 1350s.

In 1349, internal turmoil within the government necessitated Yoshiakira's return to Kyoto, where he was designated as Takauji's heir. On April 5, 1352, Loyalist forces led by Kitabatake Akiyoshi, Kusunoki Masanori, and Chigusa Akitsune seized Kyoto for a period of 20 days before Yoshiakira managed to recapture the city. In July 1353, Loyalist forces under the command of Masanori and Yamana Tokiuji once again took control of Kyoto, only to be repelled by Yoshiakira in August. In January 1355, Loyalist forces led by Momonoi, Tadafuyu, and Yamana once more captured Kyoto. However, on April 25, Takauji and Yoshiakira's combined forces successfully reclaimed the city. Following his father Takauji's passing in 1358, Yoshiakira assumed the title of Sei-i Taishogun.

Upon Takauji's death in 1358, Yoshiakira's appointment as shogun led to discord and defections within the shogunate. In 1362, Hosokawa Kiyouji and Kusunoki Masanori launched an attack on Kyoto. Yoshiakira fled the city but managed to retake it within twenty days. Later, in 1365, Prince Kaneyoshi (also known as Kanenaga), the son of Emperor Go-Daigo and leader of the rival Ashikaga court, gained control of Kyushu. In 1367, Yoshiakira fell seriously ill and passed on his position to his son.

Several months after his demise, he was succeeded by his son Ashikaga Yoshimitsu, who assumed the role of the third shogun in 1368. Yoshiakira was posthumously honored with the title Hokyoin, and his resting place is located at Toji-in in Kyoto, the same site as his father's grave.

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