He approached Ieyasu TOKUGAWA after the death of Hideyoshi, and in the Battle of Sekigahara in October 1600, he belonged to the eastern army and had great achievements such as the defense of Nagashima-jo Castle in Ise Province and the capture of Kuwana-jo Castle in Ise Province and Minakuchi-jo Castle in Omi Province.
秀吉没後は徳川家康に接近し、慶長5年（1600年）9月の関ヶ原の戦いでは東軍に属して伊勢国長島城の守備や伊勢桑名城・近江国水口城を攻略に功績を挙げた。