The origins of Katsuren Castle date back to the 12th century, according to research on the relics. From the evidence of repeated rebuilding of the castle walls, it is believed that it was fortified through a long passage of time.

The period during which Katsuren Castle was most praised for its prosperity was from the latter half of the 14th to the first part of the 15th century. This was the era when Aji lords such as Mochidzuki and Amawari were active.

Testifying to the prosperous overseas trade is the many and varied pottery wares excavated from Katsuren Castle. Not bound by the order of official trade under the royal court, the possibility that trade was proactively explored cannot be denied. In particular, the tremendous quantity of excavated items are more than adequate to know that through the trading routes, Katsuren Castle was independently able to create its prosperity.

After unification of the Sanzan (three mountain) Kingdoms, it appears that relations with the royal court were close, as evidenced by the marriage of the daughter of the Katsuren lord to the second son of Sho Hashi. Subsequently, with the change of rulers, the Aji Mochidzuki became lord of Katsuren Castle.

Mochidzuki found a young infant named Kana, later to be known as Amawari. However, Amawari, knowing full well the hardships of the people under Mochidzuki's tyranny, made up his mind to take measures. One evening, the torches of what appeared to be a long line of marching troops could be seen. Noticing movement, Amawari called Mochidzuki outside to take a look. The lord was a bit lightheaded from drink, and called on by Amawari; Mochidzuki climbed the high walls to take a better look. He was pushed off the wall by Amawari as he gazed off in the distance. This is how Amawari took the place of Mochidzuki as lord of Katsuren Gusuku. The party marching with torches was contrived by Amawari.

Amawari was seen as the savior of the people and it strengthened his status as an Aji lord.

Cautious of the increasing strength of Amawari, Chuzan King Sho Taikyu in Shuri planned to cement the relationship with the marriage of his daughter, Momoto Fumiagari, to Amawari, but in the end Amawari became a threat to the king.

An outline of the subsequent Gosamaru-Amawari Disturbance from the official histories is as follows.

When the royal court could no longer ignore the existence of Amawari, Gosamaru was moved to Nakagusuku Castle to keep watch over Amawari and their feud reached a peak. Amawari deceived King Sho Taikyu by saying that Gosamaru was planning an attack and put forward a plan to dispatch the royal armies to Nakagusuku Castle. Sho Taikyu's wife was the daughter of Gosamaru and the king, despite long years of loyalty given by Gosamaru, believed the words of Amawari. Perhaps it was the passion with which Amawari stated his case, but the king dispatched a secret messenger to Nakagusuku Castle. After hearing reports of the forces marshalling at Nakagusuku Castle, King Sho Taikyu appointed Amawari the commander of the royal armies that were sent out toward Nakagusuku. After having vanquished Gosamaru, Amawari set about achieving his ambition to overthrow the royal court and was in the midst of preparing his forces when his daughter, Momoto Fumiagari, and her vassal, Oni Ogusuku, escaped Katsuren to warn the king. Rousing his royal armies, the king attacked and defeated Amawari.

With the downfall of Amawari, no powerful lords again rose from Katsuren Castle, the resolute fortress Gusuku that it was constructed to be..

Official histories convey that Amawari was ambitious, and that under the guise of saving King Sho Taikyu eliminated rival Gosamaru first, then led a revolt against the king. In other accounts Amawari conducted overseas trade based in Katsuren Castle and was interested in advancing into the Amami Islands, in particular. This account also states there was incessant rivalry with Gosamaru over trading interests and that, conversely, it was the royal court's way of keeping away the power of Katsuren that was a threat.

It may be that this epic story of the final heroes of the ancient Ryukyu has another truth beneath its mysterious veil.