Before long, when the Kanno Disturbance, which had grown from the internal conflict in the Ashikaga family, happened, Takatsune took sides with Naoyoshi ASHIKAGA at first and became a powerful military commander, but later he took the side of Takauji ASHIKAGA.
やがて足利家の内紛から発展した観応の擾乱が起こると、はじめ足利直義方に与してその有力武将となるも、後に足利尊氏方についた。