As a general under Toyotomi Hideyoshi, Kagekatsu took part in the Odawara campaign 1590 and Korea campaigns 1592-1598, and rise to prominence to become a member of the Council of Five Elders. Originally holding a 550,000 "koku" fief in Echigo Province, Kagekatsu received the fief of Aizu, worth a huge 1.2 million "koku" when Hideyoshi redistributed holdings in 1598. After Hideyoshi's death, that year, Kagekatsu then allied himself with Ishida Mitsunari, against Tokugawa Ieyasu, as the result of some political dispute.