According to his family records, Hidehisa was the fourth son of his family, a low ranking samurai family in the Saitō clan. He was given away to another family at a young age, but eventually his older brothers died of illness and he was recalled to inherit his family name.
Mature years
Hidehisa started as a low ranking Samurai for the clan. The clan was destroyed by Oda Nobunaga and he was captured during the assault. He then became a member of the Oda clan and was ordered to serve under Kinoshita Tōkichirō. Hidehisa took part in most of the Oda clan's military actions afterwards. Slowly but steadily he rose up through the ranks. He participated in Hideyoshi's successful campaign in Shikoku. In 1581, he was made the daimyō of Awaji Domain at Sumoto Castle. In 1583, he was defeated in the Battle of Hiketa. However, in 1585, he was given charge to lead the campaign on Kyushu with two other daimyō: Chōsokabe Motochika and Sogō Masayasu. However, they were crushed in the Battle of Hetsugigawa by the Shimazu. Sogō Masayasu perished along with Chōsokabe Motochika's heir, Nobuchika. Hidehisa was accused of charging ahead too soon and then fleeing at the first sight of trouble. After he returned to Hideyoshi, he was stripped of his title, land, and sent into exile. Tokugawa Ieyasu soon arranged for him to nominally join the Tokugawa clan, and he participated in the Battle of Odawara against the Hōjō clan, where his valor redeemed his name. In 1590, he was made daimyō at Komoro with 50,000 koku revenues. Due to this series of events Hidehisa easily sided with Ieyasu in the Battle of Sekigahara after Hideyoshi's death. Hidehisa was in the army of Ieyasu's heir Tokugawa Hidetada. They were unable to reach the battle in time due to the stalling tactics of Sanada Masayuki, however Hidehisa successfully persuaded the furious Ieyasu to spare both he and Hidetada after this blunder. Hidetada remained grateful to Hidehisa for the remainder of his life. Hidehisa's family remained daiymo until the Meiji Restoration. Hidehisa is generally described as a brave and skillful warrior in his early days with Hideyoshi; he was often at the front lines of the Oda clan's military operations. He also appears to take up some of Hideyoshi's charisma, as he was able to avoid getting himself killed despite ending up in situations that would normally bode poorly for most samurai several times.
