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At first, Shigemasa served Niwa Nagahide. In 1585, after Nagahide died, Shigemasa served Toyotomi Hideyoshi and was given 10,000 koku at Echizen Province. He took part in the expedition to Kyūshū (in 1586) and Odawara (in 1590) and the Battle of Bunroku (in 1592).
In 1600, he took part in Ishida Mitsunari's force at the Battle of Sekigahara. He battled hard under the command of Ōtani Yoshitsugu. However, he died in the battle since Kobayakawa Hideaki, Wakisaka Yasuharu and others betrayed him.
Many people (according to one estimate, including those taking part in Tokugawa Ieyasu's force) regretted Shigemasa's death since he had had prowess and been respected by many daimyos.
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