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John was one of twins born in 1893 to Angus MacAskill and Marion Munro, cottars on 11/12 Ruisgarry (Quay). The family later moved to 6 Borve which his father obtained in 1900.
John was a pupil at Berneray School between 1899 and 1907 and, after leaving school, worked on his father's croft.
John married Christy Ann MacAskill of 5 Cheesebay, previously Rhuvanish. Together they were to have five children. He worked as a crofter fisherman, and was passed the croft following his father’s death in 1935.