I'm not familiar with the Kingston Board School ... perhaps someone knows more about it, but I did know that he went to St. George's College, and was nineteen years old when he joined the Civil Service. Here again is a picture of St. George's College, courtesy of the website of the St. George's College Old Boys Association, Toronto Chapter.
In his book, History of the Catholic Church in Jamaica (Chicago: Loyola Press, 1988), Father Francis J. Osborne describes the founding of St. George's in 1850 by a group of Colombian Jesuits who were newly arrived from South America, having been ejected from Colombia by the president Jose Lopez. There were objections on religious grounds from Protestant citizens, but the school went ahead offering the following curriculum: Latin, Greek, French, Spanish, English, Rhetoric, History, Mathematics, Logic, Metaphysics, Ethics, Drawing, and Calligraphy
Thanks to the Jamaica Gleaner online I've actually found a few items about my father's school days! The Gleaner of December 18, 1905 reports that St. George's College held an elocution contest at Gordon Hall on December 15th, at which "the large hall was packed, not only with the Roman Catholic community, but also a large number of citizens of other denominations". The article went on to report that Master Michael Levy of the junior division opened with "'Mary Queen of Scots' which was very nicely rendered'. Among the other contestants from the junior division were Master Harold Brodhurst, Master John Cassis, and Master Brian Sicard. The Gleaner stated that "the names of the successful competitors would be announced at the annual distribution of prizes to take place at the Theatre Royal on the 21st instant"
This was indeed the case, but unfortunately my father did not win the elocution contest. In the junior division the gold medal went to Vernon Purdon, with John Cassis, Jnr. and Brian Sicard getting honorable mention. However my father won honorable mention in several subjects at the prizegiving, including Academic, French, Arithmetic and Christian Doctrine.
This is my father's younger sister, Essie Gertrude Levy.
I assume that my father's younger brothers, Leo and Joe, would have also gone to St. George's. These two schools, along with Immaculate Conception Academy, founded in 1858 and first located on property at East Queen Street, a gift of Henry Vendryes, would have been the schools that children of Catholic families would have attended in Kingston.