He was a soldier alongside his father and brother at the age of eighteen. He was a farmer, whose respect for the Highland way of life won him a place in the legend of the country. He was an outlaw, a thief, or a dedicated family man, depending on how you look at it.
Like any Highland boy of good family, young Rob Roy MacGregor's education came from within his community, where nightly ceilidhs included games designed to strengthen the oral tradition and a child’s grasp of Highland history. His knowledge of literature, as well as politics, was considerable, particularly in a time when illiteracy was common. He was taught the skills that Highland cattle owners needed. Most importantly, his father, chief Donald Glas ensured that his children know their clan’s history and it was this aspect of his education that would most greatly influence Rob Roy’s place in history.
Along with many Highland clans, at the age of eighteen Rob Roy went to battle with his father to support the Stewart King James against his challenger, William of Orange. Although victorious in initial battles, the clans’ leader was killed and their fortunes fell. Rob’s father was taken to jail, where he was held on doubtful treason charges for two years.
Rob’s mother Margaret’s health faltered and then failed during Donald’s time in prison. By the time Donald was finally released, his wife was dead, and his reason for living also gone. The Gregor chief would never return to his former spirit or health.
For his whole life, Rob had weathered the seasonal challenges and political threats under his parents’ protection. Now, his parents and the way of life his clan had relied upon was being swept away by political winds from as far away as London and France. And his own political convictions were being formed.
From this point, Rob Roy's convictions were formed. He despised needless bloodshed and fought against the injustice that plagued his clan -- aggressively but with foresight. He was to become a hero of the Highlands.
In his early twenties, Rob worked with his brother’s cattle watch and developed his own trade in cattle. He married his sweetheart, Mary Helen MacGregor of Comar, and set about building a home for his family. This relied on long Highland customs of cattle raids, and on Rob’s own expertise in tracking and driving through the hills.
Fair and Honest
One particular raid on the herdship at Kippen landed Rob in the jail where his father had spent two years, but before his death sentence was carried out, friends were able to help him escape and he returned home to Mary and their infant son James.
It was Rob’s personality and facility for leadership, at least as much as any linear claim, that earned him respectable holdings in Inversnaid and Graigrostan, and acting chieftainship of Clan Dughaill Ciar. Rob Roy had inherited his mother's pale complexion and red hair, and it is said that he cut a striking figure. He was known as a fair and honest businessman and was considered the best swordsman in the land. At the time of his dispute with Montrose, he was well-known throughout Scotland, not only by appearance but by reputation.
Rob had been doing business with the Marquis of Montrose for ten years, borrowing large amounts of cash from him to facilitate his cattle trade. Rob had a reputation for honesty; the Marquis was known for his greed, and although Montrose had made a lot of money through his investments in MacGregor's trade, he spared no mercy for Rob. When one of Rob's agents absconded with one thousand pounds, a fortune even for a relatively wealthy landowner, Montrose pressed his advantage, hoping to claim Rob's land. After a determined search for the thief, Rob was captured by Montrose but escaped.
In 1715, Rob led his clan to battle in support of the Jacobites. He was charged with treason but again escaped from prison. He lived the rest of his life as an outlaw, taking protection from allies and making a narrow escape from enemies.
Rob Roy died at home at the age of 63. He was buried in the small churchyard in Balquidder.