Siege of Odawara (1590) participant Toyotomi Hideyoshi
Background
In 1588, Toyotomi Hideyoshi succeeded in re-unifying the nation, after several campaigns following the death of Oda Nobunaga in 1582. Hideyoshi asked Hōjō Ujimasa and Ujinao (father and son), to attend the imperial visit to Jurakudai (Hideyoshi's residence and office in Kyoto), but Ujimasa refused. However, Ujimasa proposed to reschedule the visit to spring or summer of 1590, but Hideyoshi in turn refused the proposal, which worsened their relationship. In May 1590, Hideyoshi launched the Odawara Campaign against Hōjō.The siege
The massive army of Toyotomi Hideyoshi surrounded the castle in what has been called "the most unconventional siege lines in samurai history." The samurai were entertained by everything from concubines, prostitutes, and musicians to acrobats, fire-eaters, and jugglers. The defenders slept on the ramparts with their arquebuses and armor; despite their smaller numbers, they discouraged Hideyoshi from attacking. So, for the most part, this siege consisted of traditional starvation tactics. Only a few small skirmishes erupted around the castle, as when a group of miners from Kai Province dug under the castle walls, allowing men under Ii Naomasa to enter.After three months, the sudden appearance of Ishigakiyama Ichiya Castle took away the Hōjō defenders' will to resist and they surrendered.In addition to taking Odawara Castle, Hideyoshi also defeated the Hōjō at their outposts at Hachiōji Castle, Hachigata castle, and Shizuoka in and near the southwestern part of the Kantō region. Included Shimoda fortress at Ize province, where Hideyoshi's naval forces defeated the Izu suigun. However, at Oshi castle, the defenders surrendered after hearing word that their lord had been defeated at Odawara.
The Chiba clan, allies of the Hōjō in Shimōsa, also saw Sakura Castle fall to Honda Tadakatsu and Sakai Ietsugu of the Tokugawa army during the campaign. Chiba Shigetane, daimyō of the Chiba, surrendered the castle to the besieging forces on the condition that his clan would not be abolished. While the Chiba were consequently divested of all of their holdings, many of their senior members were taken into service by Tokugawa retainer Ii Naomasa, thanks to aid he had received many years earlier from the clan during the occupation of Takeda Katsuyori's Tsutsujigasaki Castle.