In 1892, he moved to the island of Oʻahu to work at the Hawaiian Tramways Company, driving trolleys and streetcars through downtown Honolulu.

The office of mayor was created upon the insistence of Washington, D.C., despite the opposition of the Big Five oligarchy that dominated the economy of Hawaii.

Fern was multilingual, speaking Hawaiian, English, Japanese, Chinese, and Portuguese and used it to his advantage throughout his political career.

Evidence of his popularity among the people he served, Fern was granted a state funeral and was laid in the throne room of ʻIolani Palace.

During the burial rites at the King Street Catholic Cemetery, the United States Army Air Corps presented a fly-over ceremony in a v-formation.