The Third Siege of Odawara in 1590 was a pivotal moment in Toyotomi Hideyoshi's efforts to neutralize the Hojo clan as a challenge to his authority. In the months leading up to the siege, the Hojo made significant, hurried improvements to the castle's defenses as Hideyoshi’s intentions became clear. However, despite Hideyoshi's overwhelming force, there was little actual combat during the siege.
By 1588, Toyotomi Hideyoshi had largely unified Japan, following several military campaigns after the death of Oda Nobunaga in 1582. He requested that Hojo Ujimasa and his son Ujinao visit him in Kyoto at his residence, Jurakudai, but Ujimasa refused, suggesting a later visit in 1590. Hideyoshi rejected this delay, worsening relations between the two. In May 1590, Hideyoshi launched the Odawara Campaign against the Hojo.
Ujimasa hoped for support from Date Masamune or even a defection by Tokugawa Ieyasu if the conflict dragged on. Hideyoshi's massive army encircled Odawara Castle in what is often described as "the most unconventional siege in samurai history." The besieging forces were entertained by performers—concubines, musicians, acrobats, and more—while the defenders, though outnumbered, maintained their positions on the ramparts, armed with arquebuses. As a result, Hideyoshi refrained from launching a full attack, relying instead on traditional starvation tactics. Only a few small skirmishes occurred, such as when miners from Kai Province tunneled under the walls, allowing forces led by Ii Naomasa to breach the castle.
After three months, the sudden construction of Ishigakiyama Ichiya Castle near Odawara crushed the Hojo’s morale, leading to their surrender. In addition to taking Odawara Castle, Hideyoshi's forces, led by Maeda Toshiie and Uesugi Kagekatsu, captured several Hojo strongholds, including Matsuida, Minowa, Maebashi, Matsuyama, Hachigata, and Hachioji Castles. His navy, under Chosokabe Motochika, also defeated the Izu suigun at Shimoda Fortress in Ise Province.
During the campaign, the Chiba clan, allies of the Hojo in Shimosa, saw their Sakura Castle fall to Honda Tadakatsu and Sakai Ietsugu of Tokugawa’s forces. Chiba Shigetane, the clan’s daimyo, surrendered on the condition that his family would not be abolished. While the Chiba lost all their holdings, many of their senior members were later taken into service by Tokugawa’s retainer, Ii Naomasa, as a gesture of gratitude for earlier aid.
At Oshi Castle, led by Ishida Mitsunari, the defenders surrendered upon hearing of the Hojo’s defeat at Odawara. Hojo Ujimasa was unable to defend Odawara against Hideyoshi's forces, and the castle fell. Ujimasa and his brother Ujiteru were both forced to commit seppuku.
Following the campaign, Hideyoshi rewarded Tokugawa Ieyasu with the Hojo lands, not knowing that this would eventually position Ieyasu to become shogun. The siege also saw the tragic end of the tea master Yamanoue Soji, who was in the service of the Hojo lords and was sentenced to death by torture after the fall of Odawara.
See also
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The Siege of Kozuki Castle
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Siege of Nagashima Fortifications
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The Second Battle of Konodai
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The Fourth Battle of Kawanakajima
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Battle of Tonamoto (Nagahama)
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The Siege of Iwakura Castle
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