Toyotomi Hidetsugu
Despite the growing tension between the Hōjō and Toyotomi Hideyoshi, only a modest attempt was made to strength the defenses of the castle in 1586. When the Toyotomi armies attacked Odawara in 1590, Hideyoshi ordered Toyotomi Hidetsugu and Tokugawa Ieyasu to reduce Yamanaka Castle as quickly as possible, as it lie directly in his line of communications between the front lines and Osaka. In March, the two commanders attacked Yamanaka castle with 50,000 soldiers. In response, Hōjō Ujikatsu resisted with only 4,000 troops. Despite the disparity in numbers, the Toyotomi forces took heavy losses, including one general, Hitotsuyanagi Naosue; however, the castle fell in only a half day of combat and most of its defenders were killed.