In the "Taiheiki", a war chronicle written in the Muromachi period, Masashige KUSUNOKI was described as a clever general while Yoshisada, for whom the author showed little sympathy, was described as being an indecisive person who was defeated by Takauji ASHIKAGA while competing for the position as head of the samurai.
また、室町時代に成立した軍記物である『太平記』では、知略を巡らす智将として装飾的に描かれる楠木正成に対して、義貞には作者の共感が薄く、優柔不断で足利尊氏との棟梁争いに敗れる人物として描かれていると指摘される。