Nahaolelua began working for the government as a district magistrate and circuit judge on Maui. He also served as royal postmaster. During the governorship of
James Kānehoa Young, Nahaolelua served as deputy governor of Maui. Shortly after Kānehoa's death in 1851, he succeeded as
Governor of Maui, although the position was not officially confirmed until the following year on December 3, 1852. He served as Governor for twenty-two years until 1874. As a royal governor, he also held a seat in the House of Nobles, the upper house of the
legislature, traditionally reserved for the high chiefs. He sat during most of the legislative sessions between 1853 and 1874. He served as a member of the Privy Council of the King. He was elected the President of the Legislative Assembly during the sessions of 1870, 1872, and the special sessions of 1873 and 1874. During the reign of
Kamehameha V, he was made a Knight Commander of the
Royal Order of Kamehameha I.
Issue of succession, 1872–1874 . In 1872, Nahaolelua was present at the deathbed of King
Kamehameha V. Kneeling at the side of bed, with many of the members of the royal court present, he spoke with the monarch in his last attempts to name a successor to the throne. Kamehameha V, who regarded him as a close friend and business associate, asked Nahaolelua to choose an heir for him. He refused and answered, "Any one, may it please Your Majesty, of the chiefs now present." The King attempted to name his cousin
Bernice Pauahi Bishop but she refused the offer, and he died the same day without naming a successor. Because Kamehameha V died with no heir, the
constitution called for the legislature, which Nahaolelua presided over as President of the Legislative Assembly, to select the next monarch. By both popular vote, and the unanimous vote in the legislature,
Lunalilo became the first elected king of Hawaii in 1873. In private, Nahaolelua tried to persuade the new king to name a successor so the kingdom would not face another succession crisis. However, after a short reign, Lunalilo died in 1874 without an heir to succeed to him. In the election that followed,
David Kalākaua, ran against
Queen Emma, the widow of
Kamehameha IV. On February 12, 1874, for the second time in Hawaiian history, a special session of the legislature was called to elect a new monarch, and Nahaolelua was chosen again as the President of the Legislative Assembly. The assembly voted thirty-nine to six in favor of Kalākaua. The subsequent announcement caused a
riot at the courthouse as Emmaite supporters attacked and beat the native legislators who had voted for Kalākaua. American and British troops were landed, and the rioters were arrested. Nahaolelua, a known supporter and friend of Queen Emma, had left the courthouse before the riot, to bring her the news of her defeat. She reportedly sent him back with the message: "If they could not obtain their desires now, perhaps they had better wait until the morrow, when a new election for Sovereign could be had." The next day Queen Emma asked Nahaolelua about the possibility of holding a second election which he refused. ==Later life and death==