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Hojo Ujimasa (1538 – August 10, 1590) was the fourth leader of the later Hojo clan and the daimyo of Odawara. He continued his father Hojo Ujiyasu's policy of territorial expansion, achieving the largest territorial holdings in the clan's history.

Born in 1538 as the second son of Hojo Ujiyasu, Ujimasa's childhood name was Matsuchiyo-maru. After his elder brother Shinkuro passed away at a young age, Ujimasa became the heir apparent. In 1554, during an alliance formed by Ujiyasu with Takeda Shingen and Imagawa Yoshimoto, Ujimasa married Shingen's daughter, Obai-in.

Around 1559, Ujimasa assumed formal leadership of the family upon Ujiyasu's retirement. The Hojo clan expanded its control significantly under his leadership, including the capture of Iwatsuki Castle in 1560, which brought most of the Musashi Province under their control. Ujimasa participated in several key battles, such as the Battle of Konodai (1564) and the Siege of Odawara (1569).

In 1574, Ujimasa secured the surrender of Sekiyado Castle in Shimosa Province from Yanada Harusuke and gained the allegiance of Yuki Harutomi, a vassal of the Uesugi clan. The following year, Gion Castle in Shimotsuke Province, held by Oyama Hidetsuna, also surrendered. In 1577, Ujimasa invaded Kazusa Province and reconciled with his long-time adversary, Satomi Yoshihiro. This conflict marked the first battle for his heir, Hojo Ujinao.

By 1580, after Takeda Katsuyori's intervention in the Uesugi conflict and the death of Uesugi Kagetora, Ujimasa forged a new alliance with Oda Nobunaga and Tokugawa Ieyasu. The Hojo clan, alongside these allies, launched an attack on Takeda territory in Suruga, leading to the Battle of Omosu and participation in the Conquest of Koshu, culminating in the Battle of Tenmokuzan in 1582.

After Oda Nobunaga's unexpected death in 1582, Ujimasa seized the opportunity to attack Oda clan territories at the Battle of Kanagawa. Subsequently, the Hojo and Tokugawa clans settled their territorial disputes by exchanging Kai and Shinano Provinces for Kozuke Province.

In 1588, as Toyotomi Hideyoshi succeeded in unifying Japan, he invited Ujimasa and his son Ujinao to an imperial visit at the Jurakudai in Kyoto. However, Ujimasa declined the invitation, proposing a delay until the spring or summer of 1590, which Hideyoshi refused, straining their relations.

By 1590, Ujimasa had consolidated the clan's position and retired, passing leadership to his son Hojo Ujinao, who became the head of the clan and lord of Odawara. That same year, Hideyoshi launched the Odawara Campaign against the Hojo clan.


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