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In 1729 Alasdair became a schoolmaster and catechist for the Society in Scotland for the Propagation of Christian Knowledge (SSPCK) and taught at Eilean Finnan. Then in November 1732 he moved and taught at Kilmory, North Ardnamurchan (528.703). Finally from 1739 to 1745 he taught at Corryvullin, Allt an t-Siùcair, south Ardnamurchan (516.643) (Ronald Black). While working at the schools he was encouraged to produce a Gaelic-English dictionary for pupils at the Highland schools. “A Galick and English Vocabulary” was completed in 1738 but did not appear in the schools until 19th March 1741. It consists of 200 pages and the word order relates to usage-type rather than alphabetical order.
Officially, he was a Protestant, when a school master, and some of his poetry is very critical of some Catholic priests. His father had been an Episcopalian, but his brother Angus at Dalilea was an active Catholic and Alasdair displayed Catholic enthusiasm when Bonnie Prince Charlie arrived on Doutelle at Loch nan Uamh on 25th July 1745. He accompanied him as he arrived at Forsay, moved on to Kinlochmoidart and sailed up Loch Shiel to raise the standard at Glenfinnan on 19th August 1745. He received commission as Captain and served under Glenaladale who was second in command of the Clanranald regiment set up. He was responsible for interpreting Gaelic conversation for Prince Charlie and for teaching him some Gaelic language. He wrote many poems in praise of the Jacobites (John Lorne Campbell).
After Culloden, Alasdair fled and came back to Moidart where he sheltered in woods and caves, but had to flee because of the intensive searches and distructions being carried out there for the purpose of capturing Prince Charlie. Alasdair fled to Glencoe till the Indemnity Act was passed in June 1747. Then he became bailie of Canna and he and his family moved there until summer 1749. While there, he wrote about the Hanovarian atrocities being carried out on Eigg, Canna and Moidart. Curiously, he was never held or executed. In April 1751 his poetry collection “Ais-Eiridh na Seann Channain Albannaich” was published, but in 1752 most of the copies were burned in Edinburgh by the Hanovarian authorities there. About 12 copies survived and it was reprinted again in 1762 and 1802.
After Canna, Alasdair moved to Egnaig and when thrown out from there by Clanranald he wrote a ferocious poem about the horrors of that place. He moved on to Inverie (Knoydart), Camas an t-Salainn (SE of Arisaig village, 655.854) and Sanntaig (656.837) where he died.