Siege of Odawara (1590)

The third siege of Odawara (小田原征伐) occurred in 1590, and was the primary action in Toyotomi Hideyoshi's campaign to eliminate the Hōjō clan as a threat to his power. The months leading up to it saw hasty but major improvements in the defense of the castle, as Hideyoshi's intentions became clear. Thus, despite the overwhelming force brought to bear by Hideyoshi, the siege saw little actual fighting.

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 Hōjō surrendered, facing overwhelming numbers and, presumably, an impending shortage of food and supplies. Tokugawa Ieyasu, one of Hideyoshi's top generals, was given the Hōjō lands. Though Hideyoshi could not have guessed it at the time, this would turn out to be a great stepping-stone towards Tokugawa's attempts at conquest and the office of Shogun.

In addition to taking Odawara Castle, Hideyoshi also defeated the Hōjō at their outposts at Hachiōji, Yorii, and Shizuoka in and near the southwestern part of the Kantō region. The Chiba, 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, daimyo 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.

In popular culture
The Siege of Odawara is the climax of Hideyoshi's story in the video game Samurai Warriors 2. Due to the sheer size of Odawara Castle in the game, it is divided in two stages, the eastern side sieged by the Tokugawa, Chōsokabe (in Xtreme Legends only), Shimazu, and Date armies, and the western side sieged by the Toyotomi main army.