On August 31, 1891, Queen Liliʻuokalani appointed him a member of her Privy Council. In 1893 the Hawaiian Kingdom was overthrown, Kawānanakoa became a supporter of the Royalist resistance and after the failed 1895 Counter-Revolution he was arrested for treason but due to lack of evidence he was released. In 1898 he announced his engagement to Kaʻiulani, but she died in 1899 before the wedding could take place.