After coming to Honolulu, Heleluhe worked as a retainer for the royal family. He served King Kalākaua as an under-secretary. He also worked as a steward for Kalākaua's sister and successor Liliʻuokalani, and accompanied her to the leper settlement at Kalaupapa on Molokai in 1891. He steadily rose in rank until he was appointed her private secretary in 1896. In 1892. Heleluhe was nominated as a National Reform Party candidate for the House of Representatives for Oʻahu's first ward. He lost this election. After the overthrow of the monarchy in 1893, Heleluhe and his wife Wakeke Ululani remained loyal to the royalist cause and supported the deposed Queen Liliʻuokalani. Following the outbreak of the unsuccessful 1895 Counter-Revolution, Heleluhe was arrested, held as a political prisoner, and temporarily imprisoned by forces loyal to the Republic of Hawaii in order for him to "disclose the queen's treachery." Queen Liliʻuokalani, who was also imprisoned in the former ʻIolani Palace, described the ordeal Heleluhe had to endure in her 1898 memoir "Hawaii's Story by Hawaii's Queen":