Amawari, born to peasants in Yara, Chatan Magiri, Ryukyu Islands, rose from obscurity by overthrowing the lord of Katsuren Castle and seizing control. He amassed considerable wealth and power through maritime trade, elevating his regional status. His political influence grew substantially upon marrying Momoto-Fumiagari, daughter of King Shō Taikyū, solidifying his position through royal ties.

King Shō Taikyū, concerned by Amawari's growing power, commanded Gosamaru, lord of Nakagusuku Castle, to construct a fortress between Katsuren and the royal capital, Shuri. In 1458, Amawari accused Gosamaru of plotting against the king. This accusation enabled Amawari to lead royal forces against Nakagusuku Castle, defeating Gosamaru and prompting his suicide. Following this victory, Amawari plotted to overthrow King Shō Taikyū himself. His wife, Momoto-Fumiagari, and her attendant, Oni Ōgusuku, discovered the plot. Royal forces led by Ōgusuku attacked Katsuren Castle, defeated Amawari, and executed him.

Historical interpretations of these events vary. One theory posits the royal government orchestrated the conflict between Amawari and Gosamaru to eliminate both as threats to the throne. Another perspective depicts Amawari as an ambitious figure seeking power through betrayal.

Amawari's legacy remains complex. Official Ryukyu Kingdom histories typically portray him as a traitor, while the Omoro sōshi—a collection of Ryukyuan songs and legends—praises him as a heroic figure comparable to the king, reflecting divergent cultural and historical narratives. His story endures through oral traditions, kumi odori dance-plays, and modern adaptations like the "Kimutaka no Amawari" theatrical production. The ruins of Katsuren Castle, a UNESCO World Heritage Site, stand as a cultural landmark connected to his life and era.