Charles O'Leary worked as a clerk for the CNR in 1908. He served in the army during the First World War and returned to work for the CNR in 1919. He served as a conductor for the super continental train for fifteen years and retired from the CNR after forty-eight years of service.
In 1923, Charles married Gladys Bueler from Parry Sound. The couple moved to Capreol in 1925 where Charles served as the first president of the Royal Canadian Legion Branch 179. He also served as town councillor for three years.
Mr. and Mrs. O'Leary were dedicated to the Capreol community as was evidenced when they willed money to the Town of Capreol for various cultural and recreational endeavours, including the establishment of the Capreol Public Library.