Kahahana was born in the mid 18th century, about the year 1758, in the same year as Kamehameha the Great. He might have been born under the Haley's Comet yet he was not destined to unify the Hawaiian Islands, like the latter.
His father was Elani, Lord of the Ewa District. Through his father, he descend from the powerful and noble House of Ewa from the Maweke-Laakona line. His mother could be disputed. Abraham Fornander, in his book An Account of the Polynesian Race, never accounts his mother or any of Elani’s wife; but he does give his grandmother as Princess Kaionuilalahai. Solomon Lehuanui Kalaniomaiheilu Peleioholani, descendant of Kahahana, gives Kaionuilalahai as the wife of Elani. This Kaionuilalahai was the daughter of Kalanikahimakeialii and Kualii, King of Oahu and Kauai. Therefore he was nephew of Kapiohookalani & Peleioholani and cousin of Kanahaokalani & Kumahana, his four predecessors. Through his grandmother, as given by Kekoolani, Kalanikahimakeialii who was a chiefess of the highest rank, an Alii Pio, he was the great-grandson of Kaulahea II, King of Maui, and his sister bride Kalaniomaiheuila, both children of Lonohonuakini, King of Maui.
Kahahana had from boyhood been raised at the royal court of Kahekili II, at Wailuku on the island kingdom of Maui. The reason of his stay at the Mauian court was due to his mother’s relation to the warrior king of Maui. Kahahana was the first-cousin-once-removed of Kahekili through Kaulahea II and also second-cousin-once-removed of Kahekili through Lonohonuakini. Kahekili looked upon his cousin's child almost as a son of his own.
In the year 1773, two events occurred, changing Kahahana’s life forever. The first was Kumahana, the son of Peleioholani, was deposed by the Alii (chiefs or nobles) and Makaainana (Commoner) of Oahu. The second was the Royal Election of 1773, although Kumahana had grown-up children at the time, the Oahu nobles passed them by in electing a successor to the throne. The main reason of the election was not the because of the inability of Kumanaha’s children, rather it was that an elected monarch would had to heed the advice and wishes of the district nobles who place him in so high a position as Moi of Oahu. The Oahuan nobles fixed their eyes on the young son of Elani. Even though the Oahu chiefs had recently dethroned a Kualii, they still wanted one of the Kualiis to succeed to the throne; the Oahuans’ love of their old warrior king had still not diminished even after a few generations of ner’der’well successors. Kahahana was among the last of the race of Kualiis.
What share, if any, indirectly, that Kahekili may have had in the election on Oahu, is not known; but when the tidings arrived from Oahu declaring the result to Kahekili, he appears at first not to have been overmuch pleased with it. It may fairly be assumed, therefore, that he either wished to succeed himself; or he had been plotting for the conquest of Oahu and the election of his cousin would hamper his plan. The Oahu chiefs had deputed Kekelaokalani, a high chiefess, a cousin to Kahahana's mother and also to Kahekili, to proceed to Wailuku, Maui, and declare the election and solicit his sanction of the result. After some feigned or real demurrer, Kahekili consented to Kahahana going to Oahu. But Kahekili refused to let his wife Kekuapoi-ula go with him, lest the Oahu chiefs should ill-treat her. Eventually, however, he consented, but demanded as a price of his consent that the land of Kualoa in Koolaupoko district should be ceded to him, and also the "Palaoa-pae" (the whalebone and ivory) cast on the shores of Oahu by the sea.
Hampered with these demands of the crafty Kahekili, Kahahana started with his wife and company for Oahu, and landed at Kahaloa in Waikiki. He was enthusiastically received, installed as Moi of Oahu, and great were the rejoicings on the occasion.
Hampered with these demands of the crafty Kahekili, Kahahana started with his wife and company for Oahu, and landed at Kahaloa in Waikiki. He was enthusiastically received, installed as Moi of Oahu, and great were the rejoicings on the occasion. Kahahana was just 15 on the day of his accession.
Not long after his installation, Kahahana called a great council of the Oahu chiefs and the high-priest Kaopulupulu, and laid before them the demands of Kahekili regarding the land of Kualoa and the “Palaoa-pae.” At first the council was divided, and some thought it was but a reasonable return for the kindness and protection shown to Kahahana from his youth by Kahekili. But the high-priest was strongly opposed to such a measure, and argued that it was a virtual surrender of the sovereignty and independence of Oahu. Kualoa being one of the most sacred places on the island, where stood the sacred drums of Kapahuula and Kaahu-ulapunawai, and also the sacred hill of Kauakahi-a-Kahoowaha ; and the surrender of the “Palaoa-pae” would be a disrespect to the gods. In fact, if Kahekili' s demands were complied with, the power of war and of sacrifice would rest with the Maui king and not with Kahahana. Kaopulupulu represented strongly, moreover, that if Kahahana had obtained the kingdom by conquest, he might do as he liked, but having been chosen by the Oahu chiefs, it would be wrong in him to cede to another the national emblems of sovereignty and independence. Kahahana and all the chiefs admitted the force of Kaopulupulu's arguments, and submitted to his advice not to comply with the demands of Kahekili. The King of Maui was far too good a politician to display his resentment at this refusal of his demands, knowing well that he could not have the slightest prospects of enforcing them by war so long as the Oahu chiefs were united in their policy, and that policy was guided by the sage and experienced high-priest Kaopulupulu. He dissembled, therefore, and kept up friendly relations with Kahahana, but secretly turned his attention to destroy the influence of Kaopulupulu in the affairs of Oahu, and create distrust and enmity between him and Kahahana. In this object he is said to have been heartily advised and assisted by his own high-priest, Kaleopuupuu, the younger brother of Kaopulupulu, and who envied the latter the riches and consideration which his wisdom and skill had obtained for him.
Moreover, the warlike preparations of the Hawaii king Kalaniopuu, 1777—78, Kahekili against precipitating a rupture with so powerful an ally as the Oahuan King. He was but too glad to obtain the assistance of Kahahana and his chiefs in the war with Kalaniopuu. Kahahana's forces arriving from the island of Molokai just in time to share the sanguinary battle at the Waikapu. They arrived on the evening of the day that the famous Alapa regiment of Kalaniopuu was annihilated Kahekili, and joined in the next day's general battle. After the return of Kalaniopuu to Hawaii in January 1779, Kahahana went over to Molokai to consecrate the Heiau called Kupukapuakea at Wailau, and to build or repair the large taro patch at Kainalu known as Paikahawai. Here he was joined by Kahekili, who was cordially welcomed and royally entertained. On observing the abundance and prosperity of the Molokai lands, Kahekili longed to possess some of them, and bluntly asked Kahahana to give him the land of Halawa. Kahahana promptly granted the request, not being moved by the same considerations regarding the Molokai lands as those of Oahu. Molokai was conquered and subjected as an appanage or tributary to the Oahu crown by Peleioholani. At this meeting, while discussing Kahahana's previous refusal to give Kahekili the Kualoa land and the ''Palaoa-pae" on Oahu, Kahekili expressed his surprise at the opposition of Kaopulupulu, assuring Kahahana that the high-priest had offered the government and throne of Oahu to him (Kahekili), but that out of affection for his nephew he had refused. He intimated strongly that Kaopulupulu was a traitor to Kahahana.
The scheme of Kahekili was taking its course, and Kahahana returned to Oahu filled with mistrust and suspicion of his faithful high-priest. A coolness arose between them. Kahahana withdrew his confidence from, and slighted the advice of, the high-priest, who retired from the court to his own estate in Waialua and Waimea, and caused himself and all his people and retainers to be tatooed on the knee, as a sign that the King had turned a deaf ear to his advice. It is said that during this period of estrangement Kahahana became burdensome to the people, capricious and heedless, and in a great measure alienated their good-will. It is said, moreover, that he caused to be dug up dead men's bones to make arrow-points of wherewith to shoot rats — a favourite pastime of the chiefs ; and that he even ransacked the tombs of the chiefs in order to make Kahili handles of their bones, thus outraging the public sentiment of the nation. That Kahahana was imprudent and rash, and perhaps exacting, there is no doubt ; and that conquered chieftains' bones were the legitimate trophies of the victors is equally true ; but that Kahahana would have violated the tombs of the dead — an act even in those days of the greatest moral baseness — is hardly credible, and is probably an after exaggeration, either by the disaffected priestly faction or by the victorious Kahekili plotters. While such was the condition on Oahu, Kahekili reconquered the district of Hana, and, hearing of the death of Kalaniopuu and the subsequent contentions on Hawaii, he felt secure in that direction, and seriously turned his attention to the acquisition of Oahu. He first sent some war-canoes and a detachment of soldiers under command of a warrior chief named Kahahawai to the assistance of Keawemauhili, the then independent chief of Hilo, in his contest with Kamehameha I. He next sent his most trusted servant Kauhi to Kahahana on Oahu, with instructions to inform Kahahana in the strictest confidence that Kaopulupulu had again offered him the kingdom of Oahu, but that his regard for Kahahana would not allow him to accept it, and exhorting Kahahana to be on his guard against the machinations of the high-priest. Credulous as weak, Kahahana believed the falsehoods sent him by Kahekili, and, without confiding his purpose to anyone, he resolved on the execution of Kaopulupulu. Preparations were ordered to be made for a tour of the island of Oahu, for the purpose of consecrating Heiaus and offering sacrifices. When the king arrived at Waianae he sent for the high- priest, who was then residing on his lands at Waimea and Pupukea, in the Koolau district, to come to see him. It is said that Kaopulupulu was fully aware of the ulterior objects of the king, and was well convinced that the message boded him no good ; yet, faithful to his duties as a priest and loyal to the last, he started with his son Kahulupue to obey the summons of the king. Arriving at Waianae, Kahulupue was set upon by the king's servants, and, while escaping from them, was drowned at Malae. Kaopulupulu was killed at Puuloa, in Ewa.
Thus foolishly and cruelly Kahahana had played into the hand of Kahekili, who, with his high-priest Kaleopuupuu, had for a long time been plotting the death of Kahahana's ablest and wisest counsellor. The death of Kaopulupulu took place in the latter part of 1782 or beginning of 1783. Though executions "de par le roi" of obnoxious persons for political reasons were not uncommon in those days throughout the group, and by the proud and turbulent nobility generally looked upon more as a matter of personal ill-luck to the victim than as a public injustice, yet this double execution, in the necessity of which few people except the credulous Kahahana believed, greatly alienated the feelings of both chiefs and commoners from him, and weakened his influence and resources to withstand the coming storm. the hand of Kahekili, who, with his high-priest Kaleopuupuu, had for a long time been plotting the death of Kahahana's ablest and wisest counsellor.
As soon as Kahekili heard that Kaopulupulu was dead, he considered the main obstacle to his acquisition of the island of Oahu to be removed, and prepared for an invasion. He recalled the auxiliary troops under Kahahawai which he had sent to the assistance of Keawemauhili in Hilo, and assembled his forces at Lahaina. Touching at Molokai on his way, he landed at Waikiki, Oahu. Among his chiefs and warriors of note on this expedition are mentioned Kekuamanoha, Kaiana, Namakeha, Kalaikoa, Kamohomoho, Nahiolea, Hueu, Kauhikoakoa, Kahue, Kalaninuiulumoku, Peapea, Manono-Kauakapekulani, Kalanikupule Koalaukane. Besides his own armament, he had several double canoes furnished him by Keawemauhili of Hilo, and by Keouakuahuula of Kau.
Kahahana was at Kawananakoa, in the upper part of Nuuanu valley, when the news came of Kahekili's landing at Waikiki, and hastily summoning his warriors, he prepared as best he could to meet so sudden an emergency. As an episode of this war the following legend has been preserved and may prove interesting: — When the news of the invasion spread to Ewa and Waialua, eight famous warriors from those places, whose names the legend has retained, concerted an expedition on their own account to win distinction for their bravery and inflict what damage they could on Kahekili's forces. It was a chivalrous undertaking, a forlorn hope, and wholly unauthorized by Kahahana, but fully within the spirit of the time for personal valour, audacity, and total disregard of consequences. The names of these Oahu patriots were Pupuka, Makaioulu, Puakea, Pinau, Kalaeone, Pahua, Kauhi, and Kapukoa.
Starting direct from Apuakehau in Waikiki, where Kahekili's army was encamped and organising preparatory to a march inland to fight Kahahana, the eight Oahu warriors boldly charged a large contingent of several hundred men of the Maui troops collected at the Heiau. In a twinkling they were surrounded by overwhelming numbers, and a fight commenced to which Hawaiian legends record no parallel. Using their long spears and javelins with marvelous skill and dexterity, and killing a prodigious number of their enemies, the eight champions broke through the circle of spears that surrounded them. But Makaioulu, though a good fighter was a bad runner, on account of his short bow-legs, and he was overtaken by Kauhikoakoa, a Maui chief. Makaioulu was soon tripped up, secured, and bound by Kauhikoakoa, who, swinging the captive up on his own shoulders, started off with him for the camp to have him sacrificed as the first victim of the war. This affair took place on the bank of the Punaluu taro patch, near the cocoa-nut grove of Kuakuaaka. Makaioulu, thus hoisted on the back of his captor, caught sight of his friend Pupuka, and called out to him to throw his spear straight at the navel of his stomach. In hopes of shortening the present and prospective tortures of his friend, and knowing well what his fate would be if brought alive into the enemy's camp, Pupuka did as he was bidden, and with an unerring aim. But Makaioulu, seeing the spear coming, threw himself with a violent effort on one side, and the spear went through the back of Kauhikoakoa. Seeing their leader fall, the Maui soldiers desisted from farther pursuit, and the eight champions escaped.
In the beginning of 1783-some say it was in the month of January-Kahekili, dividing his forces in three columns marched from Waikiki by Puowaina, Pauoa and Kapena, and gave battle to Kahahana near the small stream of Kaheiki. Kahahana's army was thoroughly routed, and he and his wife Kekua-poi-ula fled to mountains. It is related that in this battle Kauwahine, the wife of Kahekili, fought valiantly at his side. Oahu and Molokai now became the conquest of Kahekili, and savagely he used his victory.
For upwards of two years or more Kahahana and his wife and his friend Alapai wandered over the mountains of Oahu, secretly aided, fed, and clothed by the country people, who commiserated the misfortunes of their late king. Finally, weary of such a life, and hearing that Kekuamanoha, the uterine brother of his wife Kekuapoi-ula, was residing at Waikele in Ewa, he sent her to negotiate with her brother for their safety. Dissembling his real intentions, Kekuamanoha received his sister kindly and spoke her fairly, but having found out the hiding-place of Kahahana, he sent messengers to Kahekili at Waikiki informing him of the fact. Kahekili immediately returned peremptory orders to slay Kahahana and Alapai, and he sent a double canoe down to Ewa to bring their corpses up to Waikiki. This order was faithfully executed by Kekuamanoha; and it is said that the mournful chant which still exists in the Hawaiian anthology of a bygone age under the name of "Kahahana" was composed and chanted by his widow as the canoe was disappearing with her husband's corpse down the Ewa lagoon on its way to Waikiki.
His death was in 1783, with which closed the autonomy of the island of Oahu. What followed was the Waipio Conspiracy, which ended in the extermination of the entire Oahuan nobility.