In 1403 a band of Highlanders, said to have been the Clan Stewart of Appin led by Alexander Stewart, Earl of Mar, the son of the Wolf of Badenoch murdered Sir Malcolm Drummond, chief of the Clan Drummond.

Tradition tell us that in 1445, while returning to his seat at Dunstaffnage Castle from the great cattle tryst at Crieff, Sir John met and fell in love with the daughter of MacLaren of Ardvech. Although married, he began an affair with his new love which one year later produced a son. He was christened Dugald and was to be the first Chief of the Stewarts of Appin. Sir John Stewart was born around 1410, putting him at about 35 when he met the woman that would become his second wife.

This begins the long relationship that Clan Stewart of Appin and Clan MacLaren have had. The Stewarts called upon Clan MacLaren, especially in the earlier times to fight battles against the MacDougalls and the Campbell's and their assorted henchmen. In later times, the MacLarens called on The Stewarts of Appin to assist them against the encroaching McGregors, especially Rob Roy. Indeed when Rob Roy sought to displace the Chief of Clan MacLaren from his lands and brought his men out to do the job, Clan MacLaren and Clan Stewart of Appin joined to face down Rob Roy. Seeing the McGregors outnumbered, Rob Roy offered single combat to settle the matter. Rob Roy, until that time had never been bested in a duel. Alasdair Stewart was selected as the best for the MacLaren/Stewart side. Stewart drew first blood (which was the standard of victory). While discussing this event with Donald MacLaren of MacLaren a few yards from where this all took place, he mentioned that had the battle actually taken place, it would have been the last great clan battle in Scotland by several decades.

Of course, Clan MacLaren was out with the Appin Regiment in the '45. The Stewarts of Appin did not go out as a Clan in the '45, their Chief at the time was in his minority and it was thought better to keep him above the fray. Clan MacLaren had lost their chief just a few years prior to this because Roy Roy's murderous son, Robin Og, shot him in the back. Thus, the Stewarts and MacLarens were led out in units of the Appin Regiment.

There has been some controversy from some sets of the Stewarts of Appin about the stone in Culloden reading "Clan Stewart of Appin and MacLaren." They base the controversy on published muster rolls of the time noting that MacLarens apparently had only 15 members present. This, however is a misunderstanding. Clan MacLaren is one of the older clans of Scotland. Their original homelands were in the islands and west coast of Scotland especially in the area around Appin. So some of the MacLarens went with Clan Stewart of Appin and mustered with them. However, a company of MacLarens went out as a unit and was in the Appin Regiment as a unit. They maintained their own muster rolls. These unfortunately were lost in the aftermath of Culloden. However, this is backed up by family history and genealogy. We have well known members of the family that were known as "John of Culloden" for example, who died at Culloden. Another member received a sever sword cut on his face at Culloden, neither of these people are reflected in the muster rolls of either the Appin Regiment or those MacLarens that followed the Duke of Atholl. So clearly, there is a missing piece and that is the muster rolls of the company of MacLarens.