When Emperor Godaigo's Kenmu Restoration started, Masashige served not only as yoriudo at Kirokujo, but also as secretary at Zasso-Ketsudansho and Shugo of Kawachi and Izumi Provinces.
後醍醐天皇の建武の新政が始まると、正成は記録所寄人、雑訴決断所奉行人、河内・和泉国の守護となる。