In the Battle of Sekigahara in 1600, he sided with the West squad and was the first to charge the enemy encampment as the spearhead in the battle in Fushimi-jo Castle, and he killed Mototada TORII who was shutting himself in the castle.
慶長5年（1600年）の関ヶ原の合戦では、西軍に与して伏見城攻防戦の先鋒となって一番乗りを果たし、伏見城に籠もる鳥居元忠を討ちとった（伏見城の戦い）。