Thought to have been born a son of Nitta Tomouji, a vassal based on the Nitta estate in Kōzuke (Gunma) (birth year debated). The Nitta, like the Ashikaga, descended from the Minamoto but were far less favored by the shogunate.
Angered by heavy shogunal levies, he rose at Ikushina Shrine on his home ground. Kantō warriors flocked to him and he beat the shogunal army at Bubaigawara. At Inamuragasaki, says the Taiheiki, he threw his sword into the sea in prayer and the tide drew back to let his army pass. Kamakura fell and Hōjō Takatoki and others took their own lives.
Under the Kenmu Restoration he became governor of Echigo and other provinces and head of the Mushadokoro guarding Kyoto. But most warriors leaned toward Ashikaga Takauji, and the two grew bitter rivals.
When Takauji turned against the new regime, the emperor sent Yoshisada to strike him, but he was defeated at Hakone and Takenoshita and fell back to Kyoto.
With Kitabatake Akiie and Kusunoki Masashige he drove Takauji from Kyoto to Kyūshū. But Takauji returned in strength and beat him at Minatogawa, where Masashige lost his life. When the emperor sought peace with Takauji, Yoshisada escorted Prince Tsuneyoshi and others north to Echizen.
He held Kanegasaki castle in Echizen, but besieged by Ashikaga forces and out of food, it fell. His eldest son Yoshiaki and Prince Takayoshi lost their lives; Yoshisada barely escaped and regrouped at Somayama castle.
At Fujishima in Echizen, while inspecting enemy forts with only a few men, he ran into the enemy and lost his life to a stray arrow. The Taiheiki also tells of his sad parting from his wife Kōtō no Naishi, left behind in Kyoto.
Emperor Go-DaigoAkamatsu Enshin (Norimura)Ashikaga YoshiakiraKusunoki MasashigeAshikaga Takauji
Kitabatake ChikafusaKusunoki MasashigeSasaki DōyoKō no MoronaoAshikaga TakaujiAshikaga TadayoshiNijō YoshimotoImagawa Sadayo (Ryōshun)
People of the Muromachi period ・ People by period
Based on facts found in textbooks and biographies. Uncertain points are marked as such.