His mother Juliette Montague Cooke was the teacher of future leaders of the Kingdom of Hawaii at the Royal School.

He was educated at Punahou School and Amherst Agricultural College where he roomed with friend William Owen Smith.

He was an investor in several sugar plantations in Hawaii, which became more profitable after the Reciprocity Treaty of 1875 removed tariffs.

On February 1 he was sent as a representative to Washington, D.C., in an unsuccessful attempt to have the United States annex the islands.

[3] He was a founder in 1893 of the Bank of Hawaii with Peter Cushman Jones and Joseph Ballard Atherton (his brother-in-law).

[4] He moved to California expecting to retire in 1894, but returned and became Bank of Hawaii president in September 1898 after the death of Jones.