King Kekaulike (1700-1736) was the 23rd King (Mo‘i) of Maui and founder of Maui’s last ruling dynasty.
He was descended from Pi‘ilani (‘ascent to heaven’) the Great. The Prince Maui-Loa was the first independent sovereign of Maui. Twenty generations of independent monarchs ruled in Maui from the Prince Maui-Loa until the accession of Pi‘ilani the Great who is perhaps the most renowned monarch of the island Kingdom of Maui.
The kings of Maui consolidated their strength, built up their armies and created a nation strong enough to threaten at times even the might of the powerful kings of Hawai‘i.
King Kekaulike and his children built an empire that enjoyed levels of power and prestige greater than any other royal family up until that point.
In the early-1790s, Maui’s King Kahekili (son of Kekaulike) and his eldest son and heir-apparent, Kalanikūpule, were carrying on war and conquered Kahahana, ruler of O‘ahu.
By the time Kamehameha the Great set about unifying the Hawaiian Islands, members of the Kekaulike Dynasty were already ruling Maui, Molokai, Lāna‘i , O‘ahu, Kauai and Ni‘ihau.
In the late-1780s, into 1790, Kamehameha conquered the Island of Hawai‘i and was pursuing conquest of Maui and eventually sought conquer the rest of the archipelago.
In 1790, Kamehameha travelled to Maui. Hearing this, Kahekili sent Kalanikūpule back to Maui with a number of chiefs (Kahekili remained on O‘ahu to maintain order of his newly conquered kingdom.)
Kekaulike’s son, Kamehamehanui (uncle to Kamehameha I,) lost Hana, which was isolated from the rest of Maui.
Kamehameha then landed at Kahului and marched on to Wailuku, where Kalanikūpule waited for him. This led to the famous battle “Kepaniwai” (the damming of the waters) in ‘Iao Valley (which Kamehameha decisively won.)
Maui Island was conquered by Kamehameha and Maui’s fighting force was destroyed – Kalanikūpule and some other chiefs escaped and made their way to O‘ahu (to later face Kamehameha, again; this time in the Battle of Nu‘uanu in 1795.)
There the war apparently ends with some of Kalanikūpule’s warriors pushed/jumping off the Pali. When the Pali Highway was being built, excavators counted approximately 800-skulls, believed to be the remains of the warriors who were defeated by Kamehameha.
While it may be true that Kamehameha the Great conquered Maui and overthrew the Kekaulike Dynasty at the Battle of Nu‘uanu, it should also be remembered that Kamehameha’s own mother, the Princess Keku‘iapoiwa II, was a Maui princess.
Likewise, Kamehameha’s wives of rank were princesses of Maui. These were Keōpūolani, Ka‘ahumanu, Kalākua-Kaneiheimālie and Peleuli. Keōpūolani, granddaughter of Kekaulike, was the mother of the Kamehameha II and Kamehameha III.
Others from this Maui lineage include King Kaumuali‘i (of Kauai,) Abner Pākī (father of Bernice Pauahi Bishop,) Kuakini, Keʻeaumoku II and Kalanimōkū.
The Kekaulike Dynasty was a powerful line that ruled multiple islands. Although they lost to Kamehameha, the Kekaulike lineage continued through the leadership of the future leaders of Hawai‘i.