Ena served on both
Kalākaua's Privy Council of State from 1888 to 1891 and
Liliʻuokalani's Privy Council of State from 1891 to 1893. During the reign of Liliʻuokalani, he was appointed to the Board of Health on March 30, 1891. Ena was elected to the legislative assembly in 1892. He ran as a candidate of the
National Reform Party against
National Liberal candidate E. B. Thomas. He was elected as a member of the House of Nobles, the upper house of the
legislature, for a four-year term representing the island of Oahu. From May 1892 to January 1893, the legislature of the Kingdom convened for an unprecedented 171 days, which later historian Albertine Loomis dubbed the "
Longest Legislature". During this session, Ena joined his fellow members in ousting a number of Queen
Liliʻuokalani's cabinet ministers for want of confidence, a power introduced by the
Bayonet Constitution of 1887 which empowered the legislative branch of government at the expense of the Queen. According to later testimony of
Hermann A. Widemann in the 1893
Blount Report, Ena was one of the politicians who aspired to appointment as cabinet minister. The monarchy was
overthrown on January 17, 1893, by the
Committee of Safety, with the support of United States Minister
John L. Stevens and the landing of American forces from the
USS Boston. The
Provisional Government was established until an annexation treaty with the United States could be ratified. During this turbulent time, Ena joined the side of the Provisional Government. Under the Provisional Government, Ena served on the Advisory Council to president
Sanford B. Dole, as well as on the Board of Health, and the Bureau of Agriculture and Forestry. After Dole was named as the president of Republic of Hawaii, Ena was among the same advisors who were carried over in their positions from the Provisional Government. == Personal life and investments ==