However from around 1348, he entered into a dispute with Ashikaga family steward KO no Moronao, developing into the Kanno Disturbance which split the bakufu into the Tadayoshi faction and anti-Tadayoshi faction and saw the Southern Court (Japan) entering the conflict in order to strengthen its power.
しかし、1348年（正平(日本)3年/貞和4年）頃から足利家執事の高師直と対立するようになり、幕府を直義派と反直義派の二つに割る観応の擾乱に発展し、南朝(日本)も混乱に乗じて勢力を強める。