Thought to have been born into a local gentry family of Kawachi (Osaka) (birth year debated). Little is known of his youth; some think he was a new kind of warrior involved in trade and transport.
When Emperor Go-Daigo raised his standard on Mount Kasagi, he hastened to join him; the Taiheiki says the emperor learned of him in a dream. He fought a huge shogunal army from his Akasaka castle, then set it ablaze and vanished.
Even after the emperor's exile to Oki he rose again and retook Akasaka, continuing resistance alongside Prince Moriyoshi.
Holed up in mountaintop Chihaya castle with few men, he held off a vast shogunal army for months, famed for clever tactics such as dropping boulders and logs. Meanwhile revolts spread and the Kamakura shogunate fell.
Under the Kenmu Restoration he was named governor and military governor of Kawachi and elsewhere, and served as an official of the Records Office and the claims court.
Takauji attacked Kyoto, was beaten and fled to Kyūshū. Seeing that the warriors' hearts lay with Takauji, Masashige reportedly urged the emperor to make peace with him (Baishōron), but was refused.
Ordered to meet Takauji's returning host, he stopped at Sakurai and told his son Masatsura to go home, says the Taiheiki (Parting at Sakurai). At Minatogawa (Kobe) he fought Takauji's army and took his own life with his brother Masasue, vowing, it is said, to be reborn seven times to serve the realm.
Tokugawa MitsukuniSoejima TaneomiTakamura KōunEmperor Go-DaigoAkamatsu Enshin (Norimura)Nitta YoshisadaAshikaga Takauji
Musō SosekiAkamatsu Enshin (Norimura)Emperor Go-DaigoKitabatake ChikafusaSasaki DōyoKō no MoronaoNitta YoshisadaAshikaga Takauji
People of the Muromachi period ・ People by period
Based on facts found in textbooks and biographies. Uncertain points are marked as such.