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James MacAskill, born in 1862, was the eldest son of Donald MacAskill and Hannah Ferguson of 4a Ruisgarry (Tarraloch), which was later passed to James. He became a fisherman, marrying Christina MacLeod from Sandhill in 1893. The first of their three sons was born the following year. As well as fishing and crofting, James also worked as a yachtsman, as did several other Berneray men in the early part of the 20th century.
His wife died in 1912, and two of his sons were killed during World War 1. On James' death, the croft was passed to his only surviving son Murdo MacAskill.