His birth year is unknown; he is said to have been a commoner from present-day Kadena. He overthrew Mochitsuke, the tyrannical 9th lord of Katsuren, to become its 10th lord. Praised in the Omorosaushi song anthology as 'kimotaka no mono' (a person of high spirit), he built great prosperity at Katsuren through vigorous maritime trade with China and Southeast Asia. Sho Taikyu, sixth king of the First Sho dynasty, sought to contain Katsuren's growing power by marrying his daughter Momoto Fumiagari to Amawari while also relocating the builder-lord Gosamaru from Zakimi to Nakagusuku Castle to serve as a check. In 1458, Amawari falsely reported to the royal court that Gosamaru was plotting rebellion, obtained royal sanction to attack Nakagusuku, and drove Gosamaru to take his own life (the Gosamaru-Amawari Conflict). Soon after, however, Amawari's own plot to seize Shuri Castle was exposed -- reportedly through the disclosure of his wife Momoto Fumiagari -- and he was killed when the royal army attacked Katsuren.

A man of ambition and drive who rose from commoner status through sheer ability, toppling a tyrant to seize the lordship. While possessing real economic acumen in building prosperity through maritime trade, his hunger for power ultimately led to a dramatic downfall.

The official chronicle Chuzan Seikan casts him as a traitor, but modern scholarship has offered a reassessment, viewing him as a representative of regional power resisting the centralizing Shuri court. Excavations at his seat, Katsuren Castle, uncovered Roman and Ottoman coins in 2013 -- a globally significant find attesting to the reach of trade networks in his era.