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The Mathesons of Lochalsh had been baillies to the Earl of Sutherland since the late 15th century, when they had settled on the north side of Loch Shin. During the early Jacobite Uprisings Donald Matheson of Shiness who was chief of the branch of Clan Matheson who resided in Sutherland fought against the Jacobites during the rising of 1715.
Dugald Matheson's son (Ian Og Matheson) had extensive lands in Lochalsh. He left these to Alexander, the eldest of his three sons, who purchased more land in Lochalsh. Ian Og also had a fourth son, who was killed at the Battle of Glenshiel in 1719.
The Jacobite rising of 1745, often referred to as "The 'Forty-Five", was the attempt by Charles Edward Stuart to regain the Scottish throne for the exiled House of Stuart, and recreate an absolute monarchy in Scotland and the United Kingdom. The rising occurred during the War of the Austrian Succession when most of the British Army was on the European continent. Charles Edward Stuart, commonly known as "Bonnie Prince Charlie" or "the Young Pretender," sailed to Scotland and raised the Jacobite standard at Glenfinnan in the Scottish Highlands, where he was supported by a gathering of Highland clansmen. The march south began with an initial victory at Prestonpans near Edinburgh. The Jacobite army, now in bold spirits, marched onwards to Carlisle, over the border in England. On reaching Derby, some British divisions were recalled from the Continent and the Jacobite army retreated north to Inverness where the last battle on Scottish soil took place on a nearby moor at Culloden. The Battle of Culloden ended with the final defeat of the Jacobite cause, and with Charles Edward Stuart fleeing with a price on his head. His wanderings in the northwest Highlands and Islands of Scotland in the summer months of 1746, before finally sailing to permanent exile in France, have become an era of Scottish history that is steeped in romance. John Mathieson, second of Bennetsfield, was, unlike his Lochalsh-Sutherland cousins and a Jacobite who fought at the Battle of Culloden. When the prince's army was defeated, John escaped and, according to story, fell into the hands of Hanoverian officers who were unaware of his Jacobite sympathies. He gave them some advice on the location of sound building stone, and returned safely to his home as a result.