At the Kanno Disturbance, on Tadayoshi's side, he confronted the Hatakeyama clan who was on Takauji's side, in March 1351, he attacked Kuniuji HATAKEYAMA and his father Takakuni HATAKEYAMA at Iwakiri-jo Castle in Mutsu Province (present-day Rifu-cho, Miyagi Prefecture) and made them commit suicide, but he was temporarily forced to leave Taga-jo Castle when he was attacked by Akinobu KITABATAKE of the Southern Court who took advantage of infighting in the Northern Court.
観応の擾乱には直義方として尊氏方の畠山氏と対立、観応2年2月（1351年3月）畠山高国・国氏父子を陸奥岩切城（現宮城県利府町）に攻めて自刃させたが、北朝方の内訌の機に乗じた南朝方北畠顕信に攻められ一時、多賀城を退去。