Beginning as an assistant to the Hoapili, Governor of Maui, he served many political posts including Assistant Judge of the first Supreme Court of Hawaii, an original member of the Board of Commissioners to Quiet Land Titles, a multiple-term representative in the Hawaiian legislature and circuit judge for Maui.
An early convert to Christianity and devout adherent of the Protestant faith, his first name is a Hawaiian form of the Biblical name Zerubbabel.
"[3] Kaʻauwai revered Hoapili as a father figure and accompanied him into battle and fought in the 1824 rebellion of Humehume, on the island of Kauai.
[5] With Malo, he attended the Lahainaluna became one of the first generation of Hawaiians to receive a western education by the American missionaries who arrived in Hawaii in 1820.
In their first meeting in 1832, Reverend Richard Armstrong described how Hoapili trusted him with all his important business including accessing and collecting taxes, managing his property, and conducting tours of the island of Maui, and thus became a highly respected and well-loved official in the public view.
The offer was refused by the King and his Privy Council of State, and a subsequent application dated to August 18, 1854 for a fifty-year lease at $200 per year was also declined.
[24] He also worked as a farmer and acquired property on Maui for growing taro and banana, which he won prizes for at the Hawaiian Agricultural Society in 1851.
Falling ill while he was in Honolulu, Kaʻauwai returned to his native Maui for a change of climate which did nothing to improve his health.
[23] In a letter dated to October 6, 1856, Reverend Jonathan Smith Green, who had befriended him during his lifetime as a parishioner of the Makawao church, wrote a short biography of Kaʻauwai which was published in The American Missionary.
[25] His eldest son David Kahalekula Kaʻauwai served alongside his father in the House of Representatives, from 1854 to 1855, and was considered "one of the finest Hawaiian orators".
He became the only ordained Hawaiian Anglican priest and traveled with his wife Kiliwehi as part of the retinue of Queen Emma during her trip to Europe.