At first he joined the West squad during the Battle of Sekigahara in 1600, but later he joined the East squad and captured Ujiyoshi HORINOUCHI, the feudal lord of the Kii Shingu who was in the West squad.
慶長5年（1600年）の関ヶ原の戦いでははじめ西軍に属すが、のち東軍に与して西軍方の紀伊新宮の領主・堀内氏善を攻略した。