While it is customary to portray the Lords of the Isles as divorced from the mainstream of Scottish political life, and as representatives of a brand of lordship distinct from the rest of Scotland, this view obscures the fact that Donald was only one of many magnates who held large lordships with little interference from the crown in late 14th and early 15th century Scotland.

Although he was recognised as heir-apparent (tànaiste) until Donald produced a son, he only received patches of land in Kintyre and Islay.

The Stewarts had been building up their power in the central Highlands and north of Scotland since the death of John Randolph, 3rd Earl of Moray in 1346.

Late in 1388, soon after becoming Guardian of the Kingdom, Robert Stewart, Earl of Fife (created Duke of Albany in 1398) deprived Alexander of the Justiciarship.

Alexander of Lochaber had been using his role as "protector" to further his own lordship, including granting episcopal lands to his military followers.

Sometime after 1405 but before 1411, Donald gained control of Dingwall Castle, the chief seat of the earldom and was welcomed to Ross by the people.

In the year after the death of the nominal king, Robert III, Donald sent emissaries to England, to make contact with the heir of the Scottish throne, the captive and, as yet, uncrowned James Stewart.

King Henry IV of England sent his own emissaries to Donald in the following year to negotiate an alliance against Albany.

With control over the principal seat of the earldom of Ross and support of the exiled heir to the Scottish throne, in 1411 Donald felt strong enough that he was in pursuit of a noble cause, so he marched an army of 10,000 Islesmen and Ross vassals against Albany's main northern ally, Alexander Stewart, Earl of Mar.

Although Albany appointed his own son John Stewart to the earldom, Donald's wife continued to regard herself as the rightful Countess.