Waiʻanae is mentioned in the epic of Pele and Hiʻiaka as well as the name chants dedicated to Kūaliʻi and Moʻikeha. Prior to the 13th century, Oʻahu had been divided into three kingdoms: ʻEwa (which included Waiʻanae, Kūkaniloko and the ʻEwa plains), Kona and Koʻolaupoko. Around that time, a chief from Waiʻanae, Kumuhonua, became the nominal ruler of all Oʻahu but his kingdom collapsed after his passing. Two hundred years later in the early 15th century, Kumuhonuaʻs descendant, Laʻakona re-united Oʻahu. He, too, was from Waiʻanae. He made the capital of his kingdom in Līhuʻe, Oʻahu. Līhuʻe on Oʻahu is located where Schofield Barracks is today and near the Kūkaniloko complex. The most prized warriors of Oʻahu normally came from Waiʻanae and ʻEwa because it is said that the arid rugged terrain produced people who knew how to handle hardship unlike the people on the Windward side where life seemed easier. Queen Kalanimanuia of Oʻahu, sometimes known as the Red Queen because of her kahili and feather regalia, caused to be built extensive loʻi, ditches and ponds in Waiʻanae to augment the water supply and agriculture production.
Upon her death, her sons caused Oʻahu into turmoil and shattered the peace Oʻahu had known for three generations. Napūlānahumahiki, a grandson of Kalanimanuia, proclaimed Waiʻanae independence. His sister, Kaea-a-Kalona, inherited the Waiʻanae Kingdom and married her cousin and the other main rival heir, Kākuihihewa of Kona (Oʻahu). Together Oʻahu was re-united through their union and through shrewdly utilizing the Aha ʻUla, the chiefly council. The reign of Kākuihihewa reign was a golden age of Oʻahu and the population dramatically increased–by some estimates three-fold within 40 years. As Waiʻanae was known for its warriors and itʻs claim to independence, the senior and presumptive heir to the throne of Oʻahu was then given the Lordship of Waiʻanae, ʻEwa and Līhuʻe, sort of like the title of “Prince of Wales”. This gave a presumptive heir experience in governance but also to guard Oʻahu against Kauaʻi and to ensure the loyalty of the people of the Leeward coast. But to ensure the loyalty of the peoples of the Windward coast, Kākuihihewa moved the court to Kona (Oʻahu) to his former capital. This arrangement seemed to have pleased most of the chiefs. The Kākuihihewa and Kaea-a-Kalona line produced two great Oʻahu kings–Kūaliʻi and Peleiōholani. Peleiōholani spent a lot of his time in Waiʻanae due to his wars against Kauaʻi. Peleiōholani was the first Oʻahu king to use the title of “Mōʻī”, a title previously only used by Mauiʻs kings. He also used the titles “Lord of all southern Kauaʻi, Conqueror of Molokaʻi and Lānaʻi”. Unfortunately, Peleiōholaniʻs son, Kumuhana, proved to be an awful ruler and he was deposed by the Aha ʻUla (the chiefly council) and was exiled to Kauaʻi. The Aha ʻUla then elected Kumuhanaʻs nephew, Kahahana. In 1783, Kahekili II overthrew Kahahana and became mōʻī of Oʻahu and Peleiōholaniʻs lands of southern Kauaʻi. Kahekili II then married off one of his kin to the Queen of Kauaʻi and thus Kauaʻi became a tributary of Maui. Maui thus had control of all islands except the Big Island of Hawaiʻi and 1783 marked the end of Oʻahuʻs independent kingdom–a three hundred year old kingdom that in many ways originated in the lands of ʻEwa and Waiʻanae.