Taught by Lorrin Andrews and Sheldon Dibble, Haleʻole developed a strong interest in the ancient history of his people.

Some of his classmates included early Hawaiian historians David Malo, John Papa ʻĪʻī and Samuel Kamakau.

Beckwith stated: The romance of Laieikawai therefore remains the sole piece of Hawaiian imaginative writing to reach book form.

Not only this, but it represents the single composition of a Polynesian mind working upon the material of an old legend and eager to create a genuine national literature.

A member of the first Hawaiian Historical Society, a precursor to the modern institution, he was writing a history of the life of Kamehameha I before his death.