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Donald, born in 1873, was the son of fisherman Norman MacAskill and Marion MacMillan of Borve, although whether his early childhood home was at Pol an Oir or Ferry is unclear. However, by the end of the 1880s the family were living in a newly built home at Ferry and his father was ferrying the mails. Donald worked as a postman alongside his father.
Donald married Annie Morrison of 17 Ruisgarry (Brusda) in 1895 at Lochalsh. Together they were to have nine children. In 1900 his father was allotted 23 Borve and the house at Ferry was passed to Donald. Donald worked variously as a farm labourer and yachtsman, crewing on the Golden Eagle. He was passed 23 Borve following his father’s death in 1925.
A cousin of Giant Angus MacAskill, he was known as Dòmhnall Mòr, and remembered in Sea Names of Berneray as:
‘a champion athlete especially at rowing and jumping... He was also a lobster fisherman and it is said that he held the record for never striking his boat on a rock or skerry... Big Donald, as he was known, was always immaculately dressed...'
‘It was said that Big Donald, during his Militia days, broke, on Salisbury Plains, records that stood for years... He was a wonderful athlete and I have been told that one of his favourite capers, when passing a horse and rider was to leapfrog over the horse's rear quarters and land behind the hapless rider and frighten both horse and rider to death.’
His son John Archie MacAskill is thought to have written the following verse, describing Donald at the tiller of his boat, which was named the Mary Bell:
‘Dhòmnaill Thormaid a’ Gheòidh,
‘S ‘u dòigheil ‘s an eathar,
Tha cliù ort ‘s gach dòigh,
‘S ‘u eòlach na sgeirean,
An stiùir na do dhòrn,
Is ceòth as do dheireadh.
‘S ‘u deanamh air eilean dubh Ghamhsbunn.’