Kaʻauwai was born, as the eldest son of Zorobabela Kaʻauwai and Kalanikauleleiaiwi III. His father was a successful Hawaiian politician, judge and entrepreneur who owed his rise to prominence to High ChiefHoapili, a trusted friend and companion of King Kamehameha I and the Governor of Maui. Through his mother, he descended from the ancient Hawaiian Mōʻī of Maui, Piʻilani. His mother was also a relative of Governor Hoapili. He had three siblings: William Hoapili Kaʻauwai, George Kaleiwohi Kaʻauwai and a sister who died in infancy before 1848. His niece became Princess Elizabeth Kahanu Kalanianaʻole, wife of Prince Jonah Kūhiō Kalanianaʻole, the second Congressional Delegate from the Territory of Hawaii. In January 1854, Kaʻauwai was elected as a member of the House of Representatives, the lower house of the Hawaiian legislature, for the district of Kāʻanapali on the eastern edge of the island of Maui. He was re-elected to serve a second term for the same district during the regular election of January 1854. He sat in on the legislative assembly during the regular session of 1854, the regular session of 1855, and the extraordinary session of 1855, which was called to passed the Appropriation Bill and other unfinished business from the previous session. Except for the extra session of 1855, he served alongside his father Zorobabela who was a representative for Hamakua, Maui and later Honolulu. Kaʻauwai married Jane B. Humphryes, on January 23, 1854, at Wailuku, Maui. They had no children. From 1854 to 1855, he was also an annual member of the Royal Hawaiian Agricultural Society. He was also a member of the Hawaiian bar. Kaʻauwai predeceased his father and died in Honolulu, on January 26, 1856. Later Hawaiian newspapers, reporting the election of his younger brother William Hoapili Kaʻauwai as the representative of Wailuku in 1862, noted that he was "one of the finest Hawaiian orators" and that William possessed "some of the characteristics of his brother, but has never been in public life, or had the opportunity for rhetorical display" unlike David. He was mentioned in a letter dated to June 29, 1874, written by Peter Kaʻeo to his cousin Queen Emma, a patron of his younger brother. While residing at the Kalaupapa Leper Settlement, Kaʻeo wrote how a fellow leprosy patient, Kitty Keliʻikuaʻāina Napela, wife of Jonatana Napela, had dreamed of Kahalekula, William and their mother sitting by her bedside dressed in white robes. He also mentioned that this was the third time Napela had dreamt this dream which she had described as kuluma since David's death. Both brothers and their mother had also died by the time of this third dream.
