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John, son of Murdo Montgomery and Ann Maciver, 44 Leurbost was headmaster at Knockiandue School, Keose from 1897-1900. He studied at the Free Church Training College in Glasgow and was appointed headmaster of a school in Skye before moving to Dunvegan and then to Knockiandue School in 1897.
He left for Breasclete School in 1900. He married Joanne J S Morrison of Stornoway just prior to going to South Africa in 1903. He was part of a group from the Scottish Education Department whose aim was to open new schools in South Africa after the Boer War. He was stationed in Vereeniugning, Reidleberg and Watersrand Deep in the Transvaal. John and Joanna returned to Scotland in 1911. John was appointed headmaster in Achtertyre and later in Kyle.