Although his father MINAMOTO no Yoshikuni cultivated Ashikaga so (manor) in Shimotsuke Province, the second son Yoshiyasu succeeded that, and the first son Yoshishige launched the newly reclamation work of Nitta County, Kozuke Province with his father.
父の義国は下野国足利荘を開墾したがこれは次男の義康が継承し、長男の義重は父義国とともに新たに上野国新田郡の開拓事業に乗り出す。