On April 1, 1886, Reverend William Brewster Oleson (born in Portland, Maine) was hired from Hilo Boarding School to become the first principal of the Kamehameha School for Boys. Oleson brought nine of his most prized pupils with him to Kamehameha to create the school’s inaugural class. On October 3, 1887, Kamehameha Schools for Boys opened for students and holds classes.

During a visit to see General Samuel Chapman Armstrong, Hampton’s founder, Oleson picked up the idea of including military training in Kamehameha’s curriculum (1888.) He was disciplinarian, nurse, mother and father to each boy. Oleson wrote the Kamehameha Schools alma mater, “Sons of Hawaiʻi” together with Theodore Richards, who adapted the tune from Yale’s “Wake, Freshman, Wake” and chose the school colors based on Yale school colors (‘Yale Blue’ and white.)