Battle of Sekigahara
Hideyoshi died in 1598, leaving his five-year-old son Hideyori as his successor and Tokugawa Ieyasu moved to take control. Hideie contributed 17,000 men to the Toyotomi army at the Battle of Sekigahara but they were defeated after many of their "allies" defected to the Tokugawa side. One of these defectors was Kobayakawa Hideaki, who was granted Okayama Castle and surrounding Ukita territories as the spoils of war.
Hideie escaped from the confusion of the battlefield, but was later found and exiled to the island of Hachijōjima, along with several supporters, including his two sons and their nurse(s?). Hideie's wife sought refuge with the Maeda clan and was able to correspond and send gifts (rice, sake, clothing) to her husband and sons from there.
Hideie eventually outlived his wife and all of the sengoku (warring states) era samurai. He was offered a conditional pardon after Ieyasu's death, but declined and never returned to the mainland. His wife had died, the Toyotomi were defeated, there was no place to return to, his sons had fathered children on Hachijo, and the Shogunate was to be inherited by members of the Tokugawa clan.
There is no evidence to suggest that Hideie fathered any further children himself, but many of his sons' descendants emigrated back to the Japanese mainland when a full pardon was granted at the end of the Tokugawa era.
Read more about this topic: Ukita Hideie
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