Kobayakawa Hideaki
In 1600, Wakisaka was going to side with Tokugawa Ieyasu, but was compelled to oppose him, siding with Ishida Mitsunari, who had raised Wakisaka's army when he stayed in Osaka. On October 21, during the decisive Battle of Sekigahara, Wakisaka switched sides along with Kobayakawa Hideaki, he defeated Ōtani Yoshitsugu's force, and contributed to the Tokugawa victory.