He distinguished himself at Shizugatake as being one of the "Seven Spears," and fought at Shikoku, Kyushu, Yamazaki, and other battles. In 1595, he led an army of 10000 to the monastery complex of Koyasan, to order the suicide of Toyotomi Hidetsugu. In Korea, he was in charge of the 5th Division Army, and was in charge of the administration of the province of Ch'ungch'ong.
In 1600, at a military meeting at Oyama in Shimotsuke, Masanori promptly pledged his allegiance to Tokugawa Ieyasu. He fought at the vanguard of the eastern army against the massive forces of Ukita Hideie, and for this was rewarded a fief in Bingo and Aki, amounting to 498000 koku.
After Sekigahara, Masanori started to lose his influence as the Toyotomi retainers started to die off, and though he was not prosecuted severely by Ieyasu for pledging his alliance with Toyotomi Hideyori, he was put under house arrest at Edo castle. Later, in 1619, he would come under pressure from Ieyasu and would be dissolved of his holdings in Bingo and Aki, and would have to settle with land in Kawanakaujima amounting to 45000 koku. Sadly, he remarked, "I am but a bow. During the Sengoku Jidai, I would have been treasured. Now in this age of peace I am to be stored away at Kawanakajima." He died at the age of 64.
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