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The same year [[Uesugi Kagekatsu]] came to power ([[1578]]) [[Takeda Katsuyori]] made an alliance with the Uesugi. This nullified the Takeda-Hôjô peace treaty of seven years standing and Ujimasa and Katsuyori immediately began fighting. In [[1580]] their war culminated in the [[Battle of Omosu]], a largely inconclusive affair conducted both on land and at sea around [[Izu province]]. Fighting between the two families continued sporadically until [[Oda Nobunaga]] and [[Tokugawa Ieyasu]] launched a massive invasion of [[Kai province|Kai]] and [[Shinano province|Shinano]] in [[1582]]. Hôjô contributed to the destruction of the Takeda but may have regretted Katsuyori's fall, for it now meant that a much more dangerous foe bordered the Kanto - Oda Nobunaga. Relations between the Oda and Hôjô were tense-especially when [[Takigawa Kazumasu]] began moving into Kozuke. After Nobunaga's death in June 1582, Ujimasa gathered an army and attacked Takigawa, defeating him at the [[Battle of Kanagawa]]. Meanwhile, Tokugawa Ieyasu seized Kai and Shinano-prompting Ujimasa by way of protest to bring his army to Kai. Ieyasu and Ujimasa skirmished briefly before agreeing to a truce, the result of which was that the Hôjô received land in Kai and [[Hojo Ujinao|Hôjô Ujinao]] married one of Tokugawa's daughters. When Tokugawa clashed with Toyotomi Hideyoshi in 1584 (The [[Komaki Campaign]]), the Hôjô remained neutral.  
 
The same year [[Uesugi Kagekatsu]] came to power ([[1578]]) [[Takeda Katsuyori]] made an alliance with the Uesugi. This nullified the Takeda-Hôjô peace treaty of seven years standing and Ujimasa and Katsuyori immediately began fighting. In [[1580]] their war culminated in the [[Battle of Omosu]], a largely inconclusive affair conducted both on land and at sea around [[Izu province]]. Fighting between the two families continued sporadically until [[Oda Nobunaga]] and [[Tokugawa Ieyasu]] launched a massive invasion of [[Kai province|Kai]] and [[Shinano province|Shinano]] in [[1582]]. Hôjô contributed to the destruction of the Takeda but may have regretted Katsuyori's fall, for it now meant that a much more dangerous foe bordered the Kanto - Oda Nobunaga. Relations between the Oda and Hôjô were tense-especially when [[Takigawa Kazumasu]] began moving into Kozuke. After Nobunaga's death in June 1582, Ujimasa gathered an army and attacked Takigawa, defeating him at the [[Battle of Kanagawa]]. Meanwhile, Tokugawa Ieyasu seized Kai and Shinano-prompting Ujimasa by way of protest to bring his army to Kai. Ieyasu and Ujimasa skirmished briefly before agreeing to a truce, the result of which was that the Hôjô received land in Kai and [[Hojo Ujinao|Hôjô Ujinao]] married one of Tokugawa's daughters. When Tokugawa clashed with Toyotomi Hideyoshi in 1584 (The [[Komaki Campaign]]), the Hôjô remained neutral.  
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By [[1588]] Toyotomi Hideyoshi had expanded his domain from the Tokugawa's lands to Kyushu, and sent requests to the Hôjô that they visit him in the capital. Prior to this, Ujimasa had officially retired in favor of his son Ujinao but essentially ruled alongside his son. The Hôjô response to Hideyoshi's 'requests' was to ignore them. Perhaps lulled by their alliance with the Tokugawa and by their own defensive array (which included the Hakone Mountains), Ujimasa and Ujinao waffled. Negotiations continued fruitlessly into [[1590]], at which point Hideyoshi ordered the military conquest of the Hôjô domain. In May Toyotomi forces began to descend on the Kanto-including Tokugawa Ieyasu, who advanced eastward through the Hakone passes. Uesugi Kagekatsu and [[Meada Toshiie]] marched into Kozuke and the Chosokabe, Wakizaka, Kato, and a collection of other naval-borne samurai contingents threw up a naval blockade off Odawara.
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By [[1588]] Toyotomi Hideyoshi had expanded his domain from the Tokugawa's lands to Kyushu, and sent requests to the Hôjô that they visit him in the capital. Prior to this, Ujimasa had officially retired in favor of his son Ujinao but essentially ruled alongside his son. The Hôjô response to Hideyoshi's 'requests' was to ignore them. Perhaps lulled by their alliance with the Tokugawa and by their own defensive array (which included the Hakone Mountains), Ujimasa and Ujinao waffled. Negotiations continued fruitlessly into [[1590]], at which point Hideyoshi ordered the military conquest of the Hôjô domain. In May Toyotomi forces began to descend on the Kanto-including Tokugawa Ieyasu, who advanced eastward through the Hakone passes. Uesugi Kagekatsu and [[Maeda Toshiie]] marched into Kozuke and the Chosokabe, Wakizaka, Kato, and a collection of other naval-borne samurai contingents threw up a naval blockade off Odawara.
    
The Hôjô were torn on a course of action. Ujinao was inclined to risk his 50,000 warriors all in a field battle, but the sheer magnitude of the enemy armies allowed his father and retainers to talk him into adopting a purely defensive posture. Most of the Hôjô's forces were drawn within Odawara's walls, leaving the chain of forts that acted as satellites to the main castle to fall one after another. By June some 200,000 troops were arrayed around Odawara, and the rest of the Kanto was largely in Hideyoshi's hands. It is probable that Ujimasa hoped a prolonged siege would prove too much to bear logistically for the Toyotomi forces-in much the same way that earlier attempts by the Takeda and Uesugi to besiege Odawara had failed for lack of supplies. The Hôjô themselves had an immense reserve of food-stuffs and ammunition. Unfortunately for Ujimasa and Ujinao, Hideyoshi had a brilliantly organized logistical train and all the time in the world on his side. Markets, theaters, and tournaments popped up in the Toyotomi camp, creating an almost peacetime flavor to this, the last and greatest of Hideyoshi's campaigns in Japan. Within Odawara, endless debate continued (to the extent that even today, a long, drawn-out debate or meeting that yields no results is called an 'Odawara conference'.) even as the weeks turned into months. In July, Hideyoshi demanded Odawara surrender, and [[Hojo Ujinori|Hôjô Ujinori]] (Ujimasa's brother) was sent by the Toyotomi to urge a peaceful end to the siege. To this point, there had been little actual fighting, save a few skirmishes seemingly designed to break up the monotony of the affair more than anything. An all-out assault promised to be a bloodbath for both sides. To the end, it would appear that Ujimasa, despite a growing danger of treason within the castle walls and faltering supplies, was determined to resist. Ujinao, however, was not so inclined, and finally agreed to surrender in early August. The Hôjô garrison was spared, but Ujimasa and his brother Ujiteru were made to commit suicide.  
 
The Hôjô were torn on a course of action. Ujinao was inclined to risk his 50,000 warriors all in a field battle, but the sheer magnitude of the enemy armies allowed his father and retainers to talk him into adopting a purely defensive posture. Most of the Hôjô's forces were drawn within Odawara's walls, leaving the chain of forts that acted as satellites to the main castle to fall one after another. By June some 200,000 troops were arrayed around Odawara, and the rest of the Kanto was largely in Hideyoshi's hands. It is probable that Ujimasa hoped a prolonged siege would prove too much to bear logistically for the Toyotomi forces-in much the same way that earlier attempts by the Takeda and Uesugi to besiege Odawara had failed for lack of supplies. The Hôjô themselves had an immense reserve of food-stuffs and ammunition. Unfortunately for Ujimasa and Ujinao, Hideyoshi had a brilliantly organized logistical train and all the time in the world on his side. Markets, theaters, and tournaments popped up in the Toyotomi camp, creating an almost peacetime flavor to this, the last and greatest of Hideyoshi's campaigns in Japan. Within Odawara, endless debate continued (to the extent that even today, a long, drawn-out debate or meeting that yields no results is called an 'Odawara conference'.) even as the weeks turned into months. In July, Hideyoshi demanded Odawara surrender, and [[Hojo Ujinori|Hôjô Ujinori]] (Ujimasa's brother) was sent by the Toyotomi to urge a peaceful end to the siege. To this point, there had been little actual fighting, save a few skirmishes seemingly designed to break up the monotony of the affair more than anything. An all-out assault promised to be a bloodbath for both sides. To the end, it would appear that Ujimasa, despite a growing danger of treason within the castle walls and faltering supplies, was determined to resist. Ujinao, however, was not so inclined, and finally agreed to surrender in early August. The Hôjô garrison was spared, but Ujimasa and his brother Ujiteru were made to commit suicide.  

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