[1] Her father was an immigrant from Canada, who had replaced Antone Rosa as Kalākaua's Attorney General after the signing of the 1887 Constitution of the Kingdom of Hawaii.
For his alliance with Liliʻuokalani during the overthrow, he spent seven years in exile in San Francisco, returning to Hawaii after its annexation by the United States.
[2] President Woodrow Wilson appointed him First Judge of First Circuit Court, District of Hawaii in 1914, a position he held until his retirement.
She then spent several weeks in Hawaii accompanying her father in his judicial duties,[4] before enrolling at the University of Michigan, receiving her JD degree in 1915.
[7] In February 1916, while still living in her parents' house and being financially supported by them, Ashford acted as the defense in a case in which her father presided over as the judge, raising conflict of interest concerns.
[12] When she worked as counsel for the Territorial Senate, the newspaper stated that during the period she served in that position, she earned a higher salary than any other public servant.
[17] In August of that year, she was un-retired by Chief Justice Samuel B. Kemp, who appointed her to fill a District Magistrate vacancy on the island.