Okaia, a native of Hawaii, enlisted with the Hudson’s Bay Company in 1840 at O’ahu and began his employment at Fort Stikine (1840-1843). While at Fort Stikine, servants rebelled against John McLoughlin Jr.’s charge. The court depositions given by the Hawaiian witnesses (including Okaia) of the murder of McLoughlin illustrates the linguistic difficulties faced by those working at the forts, where most interactions were in Chinook Jargon/Wawa (a trade language), as well as French-Canadian, native dialects, or Hawaiian. In 1843, Okaia transferred to Fort Victoria, where he worked as a labourer. The Fort Victoria Journal recorded his status on 11th April, 1847 as “one of the mill men.” Okaia returned to O’ahu, likely aboard the barque Cowlitz (7th December, 1848). In 1850, he returned to Fort Victoria, remaining until his death in 1854.