In contrast to his elder brother Takauji who was emotionally unstable (he was ashamed of becoming an enemy of the Imperial Court and left the battle only to briefly enter the Buddhist priesthood), Tadayoshi is thought to have been calm, and to have supported his elder brother in important positions.
兄・尊氏が感情の起伏を持っていた（朝敵となったことを恥じて戦いを離れ一時出家したりしている）人物とされているのに対し、冷静沈着であったとされ、要所で兄を支えている。