Like many others men of this period, he began his career in 1336, at the end of the Kenmu Restoration. He fought many battles all over the country, including 1336's attack to Mount Hiei. In 1338, together with cousin Moroyasu, he went to fight against Southern Court forces in Aonohara, Mino Province, to help contain Kitabatake Akiie, who was threatening Kyoto. The next year he was made Kantō shitsuji, counsellor to Ashikaga Yoshiakira, holding the post until 1944. He proved successful in this role against both the pro-Ashikaga Tadayoshi Uesugi clan and against Hitachi Province's Kitabatake Chikafusa, who was the main military force behind the Southern court. He defeated Chikafusa first in December 1341 and then two years later, finally driving him out of Kantō. He was concurrently also shugo of Musashi Province from 1341 to 1344.