When the Ashikaga's troops established themselves in Kyushu and approached Kyoto again in 1336, Masashige suggested to Emperor Godaigo that the emperor should abandon Yoshisada NITTA to make peace with Takauji, but the Emperor did not accept his opinion, then Masashige advised him to take the second best policy, that is, a temporary withdrawal from Kyoto, which was also rejected.
延元元年/建武3年（1336年）、足利方が九州で軍勢を整えて再び京都へ迫ると、正成は後醍醐天皇に新田義貞を切り捨てて尊氏と和睦するよう進言するが容認されず、次善の策として、一旦天皇の京都からの撤退を進言するがこれも却下される。