Upon obtaining his Juris Doctor degree, he served in private practice at the law firm Case, Bigelow & Lombardi until 2000.

[citation needed] He was a member of the inaugural 1997 class of the Pacific Century Fellows.

He ran and won an election for the Hawai`i State House of Representatives, an office he served through 1998.

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.

[1] In the primary elections held on September 24, 2006, Kawānanakoa was narrowly defeated by State Senator Robert Hogue.