Entering the period of the Northern and Southern Courts, under an excellent military commander Enshin AKAMATSU, the clan supported Takauji ASHIKAGA, who estranged from the Kenmu Restoration, due to being deprived of the province where he ruled as a provincial constable in the Kenmu Restoration carried out by the Emperor Godaigo.
南北朝時代(日本)に入ると、名将・赤松円心のもと、後醍醐天皇の建武の新政で守護国を没収されたことなどから新政から離反した足利尊氏に味方した。