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Archibald, or Gillespie, was born in 1845, the son of John MacLeod and Ann MacDonald of 5 Balmartin. He was initially apprenticed to a doctor in Barra, but was thrown from a horse and damaged his shin bone, which ended his career in medicine. Instead he went to Glasgow, where he spent six years apprenticed to a tailor.
In 1885 he married Ann MacKillop of Lamerick. They were to have seven children together, making their home and running their business from a new house at Pol an Oir.
Not far from their home were two rocks, named Gillespie's Rock and Gillespie's Skerry for a previous resident of the area, but the coincidence of the name led to them being renamed the Tailor's Rock and the Tailor's Skerry, which didn’t necessarily please Archibald, who was keen to preserve the original place-names.
His grandson Donald MacKillop writes of him on page 55 of Coille an Fhàsaich:
Although he had a limp and a crutch all his days, he owned two boats - fairly large ones - which he used for bringing home peat, fishing, and to ferry people back and forth across the Sound of Uist.
He played the fiddle and chanter and was a popular man, full of wit, as recalled by Ian Paterson on page 753 of An Tuil:
Gilleasbaig was frequently the butt of his customers' practical jokes, but responded in kind. When he had finished an article for one of his tormentors he would say,
"A Dhia, seo dhuit i a-nis! Tha i cho math 's ged a thigeadh i à buth a Glaschu!"
"Well, here it is now! It's as good as if it had come from a shop in Glasgow!"
And it would be short in the arm or wide in the leg…