Ragsdale was born in , a
hapa-haole or half-
Hawaiian, half-Caucasian. His father Alexander Ragsdale was an American plantation owner originally from
Virginia who had settled in Hawaii in 1817 and married Kahawaluokalani (Kahawalu), a minor Hawaiian chiefess and a descendant of King
Kekaulike of
Maui and his wife Kahawalu. His siblings were Edward Alexander Ragsdale (1839–1863) and Annie Green Ragsdale Dowsett (1842–1891), who married James Isaac Dowsett. He was considered a distant relative or cousin of
Queen Emma. From 1861 to 1865, Ragsdale served as the first editor of
Ka Nupepa Kūʻokoʻa ("The Independent Newspaper") for publisher
Henry Martyn Whitney. After four years, he was replaced by missionary
Luther Halsey Gulick, Sr. in 1865. His
Roman Catholic faith was a probable reason why he was replaced, since the Hawaiian
Congregationalists wished to have a newspaper more favorable to them. In 1866, Ragsdale was working as a government translator and interpreter for the
Hawaiian legislature. American writer
Mark Twain visited the island kingdom at the time and described the legislative session and Ragsdale: Bill Ragsdale stands up in front of the Speaker's pulpit, with his back against it, and fastens his quick black eye upon any member who rises, lets him say half a dozen sentences and then interrupts him, and repeats his speech in a loud, rapid voice, turning every Kanaka speech into English and every English speech into Kanaka, with a readiness and felicity of language that are remarkable – waits for another installment of talk from the member's lips and goes on with his translation as before. His tongue is in constant motion from 11 in the forenoon till four in the afternoon, and why it does not wear out is the affair of Providence, not mine. There is a spice of deviltry in the fellow's nature and it crops out every now and then when he is translating the speeches of slow old Kanakas who do not understand English. Without departing from the spirit of a member's remarks, he will, with apparent unconsciousness, drop in a little voluntary contribution occasionally in the way of a word or two that will make the gravest speech utterly ridiculous. He is careful not to venture upon such experiments, though, with the remarks of persons able to detect him. I noticed when he translated for His Excellency
David Kalakaua, who is an accomplished English scholar, he asked, "Did I translate you correctly, your Excellency?" or something to that effect. The rascal. ==Superintendent of Kalaupapa==