Hirate Masahide (平手 政秀, June 4, 1492-February 25, 1553) was a samurai who served the Oda clan for two generations. His original name is Hirate Kiyohide (平手 清秀).
Masahide first serves Oda Nobuhide. He is talented not only as a samurai but also in various arts such as sado and waka and this helps to enable him to act as a skilled diplomat, dealing with the Ashikaga shogunate and the emperor's representatives.
In 1533, a well-known regent, Yamashina Tokitsugu, visited Owari province, the region dominated by the Oda clan. Appreciating the munificence of the reception prepared by Masahide, Tokitsugu highly praised the knowledge of his host.
Another proof of his importance as a diplomat is the fact that he visits Kyoto in order to offer the cost of repairing the emperor's residence on behalf of Nobuhide.
When Nobuhide's son Nobunaga was born in 1534, Masahide became the second highest ranking karō as well as the guardian of the new heir. In 1547, Nobunaga completed his second year of the coming of age ceremony and in his first battle, Masahide served by his side.
In the following year, he worked to establish peace between Nobuhide and his lifelong rival, Saitō Dōsan of Mino province, and to arrange a marriage between Nobunaga and Nō-hime, Dōsan's daughter. This move allows the Oda clan to focus on fighting the Imagawa clan.
In this way, Masahide faithfully serves the Oda family but is also deeply troubled by Nobunaga's eccentricity. After Nobuhide's death, the discord in the clan increases as well as Masahide's concerns about his master's future. Desperate, Masahide killed himself in 1553.
Masahide's suicide is commonly portrayed as the story of the obliged sage who admonishes his young master with his own death. However, this may not be the true story. Some commentators believe that Masahide felt responsible for Nobunaga's behavior and took responsibility for his own life.
Others think that after Nobunaga asked for Masahide's son's horse and Masahide refused, Masahide was faced with a difficult situation. Still other observers think that there were serious conflicts with other vassals.
Nobunaga did not become less erratic after Masahide's death, but he mourned it and built Seishu-ji (政秀寺), a Buddhist temple dedicated to Masahide.