At the Genko War, he is considered to have followed the head family of Ashikaga along with other Kira family members, at Kenmu Restoration, he went down to Kanto region, following Tadayoshi ASHIKAGA, younger brother of Takauji ASHIKAGA, and he was appointed as the third tonin (the director) of the six banshu (guards) of Kanto Hisashi ban (people who keep the night watch staying under the eaves of building) in February 1334, getting the assignment to guard Imperial Prince Nariyoshi.
元弘の乱では他の吉良一族とともに足利宗家に従ったと考えられ、建武の新政期に足利尊氏の弟・足利直義に従い関東に下向、建武(日本)元年正月（1334年2月）に関東廂番（かんとうひさしばん）六番衆の第三番の頭人に任ぜられ、成良親王警護の任を負った。