James Kealoha graduated from Hilo High School and operated a grocery business in Hilo for nearly two decades. He entered politics early, serving in the Hawaii Territorial House of Representatives and later the Hawaii Territorial Senate, where he switched party affiliations. Kealoha held various county positions, including six terms as county chairman, and served as lieutenant governor. Despite multiple unsuccessful bids for higher office, he remained active in public service, including a role at the New York World's Fair.

James Kealoha's political career reveals a distinctive blend of localism and anti-establishment views, particularly in economic policies. His opposition to Quinn's land and highway trust fund proposals suggests a preference for maintaining existing structures over large-scale reforms. Kealoha's foreign policy stance, strongly against the Vietnam War, contrasts with typical Republican positions of his era, showcasing an ideological agility that defies conventional categorization. His personal financial troubles, including bankruptcy and falling victim to a scam, add an intriguing layer of vulnerability to his public persona.