When Hideyoshi died in 1598, Tadaoki, now a daimyo (feudal lord) of the military faction in his own right, was in conflict with Mitsunari ISHIDA and his comrades in the administrative faction and on good terms with Ieyasu TOKUGAWA.
慶長3年（1598年）8月に秀吉が死去すると、武功派大名の一人として石田三成ら吏僚派と対立し、徳川家康と誼を通じた。