After Hideyoshi died in 1598, Kiyomasa approached Ieyasu TOKUGAWA, one of the Gotairo (Council of Five Elders) and he married an adopted daughter of Ieyasu as the second wife.
慶長3年（1598年）に秀吉が死去すると、五大老の徳川家康に接近し、家康の養女を継室として娶った。