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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Battle of Tenmokuzan
The Battle of Tenmokuzan in 1582 is remembered as the final stand of the Takeda clan in Japan. This battle marked the last attempt by Takeda Katsuyori to resist Oda Nobunaga's relentless campaign against him. Fleeing from his pursuers, Katsuyori set fire to his fortress at Shinpu Castle and sought refuge in the mountains at Iwadono, a stronghold held by his loyal retainer, Oyamada Nobushige. However, Oyamada betrayed Katsuyori, denying him entry. Left with no other option, Katsuyori committed suicide alongside his wife, while the remnants of his army made a valiant effort to hold off their attackers.
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Battle of Oshu
The Northern Fujiwara clan had governed the Mutsu and Dewa provinces since 1087, maintaining their rule for over a century by 1189. The clan was founded by Fujiwara no Kiyohira, alongside Minamoto no Yoshiie, who established their independence in Hiraizumi, located in present-day Iwate Prefecture. Under Kiyohira, and later his successors Fujiwara no Motohira and Fujiwara no Hidehira, the Northern Fujiwara reached the height of their power in the Tohoku region. They infused the area with Kyoto culture and constructed significant temples, such as Chuson-ji, founded in 1095.
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Battle of Omosu
The 1580 Battle of Omosu (Omosu no Tatakai) was one of many conflicts between the Hojo and Takeda clans during Japan's Sengoku period. What sets this battle apart is its rarity as one of the few naval engagements in pre-modern Japan. The conflict occurred off the coast of the Izu Peninsula, involving the fleets of Hojo Ujimasa, the leader of the Hojo clan, and Takeda Katsuyori, the head of the Takeda clan.
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The Battle of Azukizaka
The Battle of Azukizaka, also known as the Battle of Bato-ga-hara, occurred in 1564, as Tokugawa Ieyasu aimed to quash the emerging threat of the Ikko-ikki, a coalition of monks, samurai, and peasants strongly opposed to samurai rule.
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Battle of Osaka
Upon Toyotomi Hideyoshi's death in 1598, Japan entered a period of governance by the Council of Five Elders, with Tokugawa Ieyasu wielding the most influence. Following his victory over Ishida Mitsunari in the Battle of Sekigahara in 1600, Ieyasu effectively seized control of Japan and disbanded the Council. In 1603, the Tokugawa shogunate was established in Edo, with Hideyoshi's son, Toyotomi Hideyori, and his mother, Yodo-dono, permitted to reside at Osaka Castle. Hideyori was granted a significant fief valued at 657,400 koku but remained confined to the castle for several years. As a means of control, it was arranged for Hideyori to marry Senhime, the daughter of Hidetada, in 1603, who had ties to both clans. Ieyasu aimed to establish a strong and stable regime under his clan's rule, with only the Toyotomi, led by Hideyori and influenced by Yodo-dono, posing a challenge to his ambitions.
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Battle of Shizugatake
The Battle of Shizugatake, occurring during Japan's Sengoku period, unfolded between Toyotomi Hideyoshi (then known as Hashiba Hideyoshi) and Shibata Katsuie in Shizugatake, Omi Province, spanning two days from the 20th day of the fourth month of Tensho 11 (equivalent to June 10-11, 1583, on the Gregorian calendar). Katsuie, supporting Oda Nobutaka's claim as successor of Oda Nobunaga, engaged in a succession dispute within the Oda clan, ultimately favoring Hideyoshi.
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Battles of Kizugawaguchi
The pair of Kizugawaguchi Battles took place during Oda Nobunaga's endeavors to besiege the Ishiyama Hongan-ji in Osaka. Serving as the stronghold of the Ikko-ikki, a coalition of warrior monks, priests, and farmers in opposition to Oda's rule, the Hongan-ji posed a formidable challenge. To counter the Ikko-ikki's attempts to supply the fortress and break the siege, Oda commanded Admiral Kuki Yoshitaka to organize a blockade against their allies' fleets. Among the opposition were influential families, notably the Mori Terumoto from the Mori clan in neighboring provinces.
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The Battle of Okehazama
In the year 1560, Imagawa Yoshimoto, a formidable warlord who held dominion over the provinces of Suruga, Totomi, and Mikawa, gathered a mighty army of 25,000 men. His objective was to march upon Kyoto, challenging the increasingly feeble and ineffectual Ashikaga shogunate for control of Japan. The army traced its path along the Tokaido highway, crossing from Mikawa into Owari province, recently unified by the local warlord, Oda Nobunaga.
