In 1994, Kawānanakoa followed in his ancestors' footsteps and got involved in politics. Like his great-grandmother Abigail Campbell Kawānanakoa and great uncle Prince Jonah Kūhiō Kalanianaʻole, Kawānanakoa joined the Republican Party of Hawaii for its pro-business stance. He ran and won an election for the Hawai`i State House of Representatives, an office he served through 1998. He rose through the ranks of party leadership becoming minority floor leader. During an attempt to mount a challenge for the Congressional seat held by Neil Abercrombie, Kawānanakoa abruptly retired from active political life after being hospitalized.
In April 2006, after eight years out of the public eye, Kawānanakoa announced his run for the Congressional seat held by Ed Case, who chose not to run for U.S. Senate. He declared his candidacy on April 23, 2006.[1] In the primary elections held on September 24, 2006, Kawānanakoa was narrowly defeated by State Senator Robert Hogue. The final vote total was Hogue: 8,393 votes (45.6%) vs. Kawānanakoa: 8,194 votes (44.5%). Senator Hogue went on to lose to Mazie Hirono.
In 2008, Kawānanakoa unsuccessfully ran for the Hawaii State House of Representatives. His opponent in the November 4, 2008, election was Democrat Chris Kalani Lee. Lee won with 5,885 votes to Kawānanakoa's 3,374 votes.[3]
