His birth year is unknown. Renowned for his valor, he was known by the epithet 'Oni Ufugusuku' (Demon Ufugusuku) and later, upon becoming administrator of the Goeku district, was also called Oshiro Kenyu. In 1458, when Amawari, lord of Katsuren, plotted to seize Shuri Castle, Oshiro was appointed commander-in-chief of the royal army to thwart the ambition, storming Katsuren Castle and killing Amawari. This feat won him great standing at court, but in 1469, when the powerful lord Kanamaru (later King Sho En) seized the throne in a coup, Oshiro found himself increasingly at odds with the new regime. Pursued as a fugitive, he is said to have fled into a cave at Chibana Castle, where he was attacked with fire and took his own life.

A leading warrior of the royal court who crushed Amawari's ambitions, he was ultimately swept up by the political upheaval of a dynastic coup, transformed from a figure of glory into a hunted fugitive -- a tragic warrior's tale.

He is remembered in Ryukyuan history as the key figure who brought the Gosamaru-Amawari Conflict to its end, while Chibana Castle, said to be the site of his death, is recalled as the historic site marking the dramatic close of his life.