After Hidemasa's death, he served under Hidenaga TOYOTOMI and then Hideyoshi TOYOTOMI; then he took the side of TOYOTOMI clan and took part in the Battle of Komaki-Nagakute (the battle between Hideyoshi HASHIBA (the former name of Hideyoshi TOYOTOMI before getting granted the name TOYOTOMI) and Ieyasu TOKUGAWA with Nobukatsu ODA), the Siege of Odawara (the war between Hideyoshi TOYOTOMI and the Hojo clan still influential in Kanto region based on Odawara) and invasion of the Korean peninsula (the invasion of Korean peninsula promoted by Hideyoshi TOYOTOMI).
秀政の死後、豊臣秀長、次いで豊臣秀吉に仕え、小牧・長久手の戦い、小田原征伐・朝鮮出兵などに従軍。