John of Isla MacDonald was succeeded by his eldest son by his second marriage to Margaret Stewart. His father had previously made provision for his sons by his first marriage. His eldest son John, whose mother was Amy McRuarie was given the lands of Garmoran and the North Isles which had been the lands of his mother's clan and were near to half of his father's holdings. In addition to this he received the lands of Swynort, Letter-Lochletter, Ardgowar, Hawleste, and 60 marklands in Lochaber. In this charter from the crown of Scotland, he is to hold these lands of his father John and his heirs. In effect he was to be a vassal of his younger half-brother. So, although he was the eldest of the living sons of John of Isla, Reginald was not his heir. Reginald was Donald's vassal and Reginald's descendants were the vassals of Donald's descendants.
Archibald MacDonald says in his book that the Book of Clanranald says that Reginald was High Steward of the Isles and that he gave over all the rights and privileges of the lordship of the Isles to Donald at Kildonan, in Eigg, and that Donald was nominated MacDonald and Donald of Isla, in presence of the principal men of the Isles. Donald was now feudal superior to his brothers and also chief of Clan Donald. The principal men of the clan could elect whomever they chose to be their chief. The Book of Clanranald states that Reginald died in 1386, and it appears from a charter in July of 1389, that his younger full brother Godfrey inherited his possessions. He kept these possessions even though they were conferred on Reginald's heirs by Robert III. I have not found any sources which say whether or not Reginald's heirs contested Godfrey taking their father's lands. But if they did, they must not have been successful in regaining them.
Donald besides being the superior lord of the Clan MacDonald and all its territories also received the lands of Colonsay and others not given to the younger sons in the grants. John Mor Tainistear, was the second son by the second marriage of John of Isla and Donald's younger brother. He received a grant of 120 marklands in Kintyre and 60 marklands in Isla. He was the founder of the MacDonald's of Dunnyveg and the Glens, which he gained by his marriage to Margery Bisset. John lived in the Castle of Dun-Naomhaig on Isla, but Donald lived in Finlaggan Castle on Isla. John and Donald's younger brother Angus died young without issue. Their next younger brother was named Alasdair, known as Alasdair Carrach, who was the founder of the family of MacDonalds of Keppoch. He was given lands in Mull and also the lands of Lochaber,
Archibald MacDonald says that there was still another younger brother called Hugh. He was granted a charter of the whole thanage of Glentilt, and referred to as the brother of Reginald of the Isles. Since these lands were granted by the Steward, Archibald assumes that he was Steward's grandson.
To return to Donald, Lord of the Isles, as previously mentioned in the story of his father, John of Isla. Doanld was given as a hostage in the year 1369 in order to ensure his father's good behavior. Donald was probably about ten years of age at that time, assuming that John's second marriage took place in 1358.
In 1378 a safe conduct was granted to him by Richard II whom he had been visiting in England. The document refers to him as the brother of John of Isla, clerk, John having been educated for the church. In 1382, Hugh of the Isles visited England, probably as an ambassador from his father, and was given a safe conduct and an escort of six men. In 1388 Donald visited the English,with his brother John Mor and his elder half-brother Godfrey, at which time, they were received as independent princes. While they were in England, they entered an allegiance with Richard II and John, now Bishop of the Isles is a party to this agreement.
In 1400 Donald and his brother John are given safe conduct and an escort of 80 horsemen. Just by the fact that their escorts seem to be growing in size, it can be surmised that Donald and his brother were being treated with increasing distinction by the English.
Donald and his two brothers visited England again in 1400, and returned in 1405 and 1408 to renew their allegiance to the King of England. Donald and his brothers remained on friendly terms with Richard II and when he was removed from the throne and sent to Pontefract Castle and Henry of Lancaster was placed on the throne in his place, he escaped from his captors and traveled disguised as a beggar to Finlaggan Castle in Isla where he was recognized by John Mor's wife. He was shown kindness and hospitality as well as asylum until a safer asylum could be secured for him with the king of Scotland.
Donald and his brothers being so friendly to the English over their own Scottish royal relatives caused them to be accuse of not having enough filial affection for their mother, who was the king's sister. It is most probably that this insinuation against their honor was really aimed at requiring them to be less independent of the Scottish throne and to add insult to injury, the king ordered the Earl of Fife to protect his sister. The interference into their business and the inference that their mother needed to be protected from them caused them to immediately rebel against the king. This enmity towards the crown may have been responsible for Donald and his brother joining in the conflict over the Earldom of Ross. The Earl of Ross died in 1394. Donald's brother Alasdair Carrach, with the aid of Donald joined in the fighting and took possession of the Castle of Uruquart, which was part of this earldom. Alasdair was imprisoned as a result of this. Donald was required to be his jailer and when he released his brother a year later, Donald was summoned to appear before Parliament to answer for his prisoner in order that the king might make a show of royal anger.
When Robert III of Scotland died, and the Duke of Albany was made Regent of the Kingdom, Donald does not appear to have either supported or opposed it, because it was not having any effect on his family's interests or on his own independence.
When it was rumored that Euphemia Lesley, daughter of Alexander Lesley, Earl of Ross might give up her rights, he again took an interest in Scottish politics. The earldom of Ross was partly made up of lands that had at one time belonged to his family in Argyle. But his claim to the Earldom of Ross came from his marriage to Lady Margaret Lesley, who was the nearest living relative in line of succession after Euphemia Lesley. The Duke of Albany who was Regent of the throne was the other chief contender for the Earldom of Ross. Aside from gaining a valuable property, it would have been in his interests to keep Donald of Isla or his brothers from gaining the earldom, in order to curb any increase in their power, which he would have perceived as a threat.
Donald's wife Margaret would have been the heir to the earldom if Euphemia died without naming an heir. The Duke of Albany by some means influenced her to enter a convent and dedicate her life to heavenly pursuits. As long was not of a legal age to resign her rights to the earldom and remained in the convent, the Duke had only to bide his time. Donald's position however became that if Euphemia had given herself as the bride of heaven that she should be considered legally dead, in which case he and his wife had the right to the earldom, since she had not named an heir before entering the convent. Donald was prepared to fight for what he believed rightfully his. The whole clan MacDonald from the Isles and from his holdings on the mainland gathered in preparation to fight with him. Donald MacDonald and his fleet arrived on the West Coast of Rossshire and landed at Strome. They marched through the glens of Ross and soon reached the vicinity of Dingwall. But they were met by the largest clan living in this vicinity, the clan of Mackay. Angus Dubh Mackay intended to stop them from going any further. Donald MacDonald and his forces routed Mackay's clan. Angus Dubh Mackay was taken prisoner and his brother Rory was killed. Donald took possession of the Castle of Dingwall and garrisoned it and then continued on his march toward Inverness. On the way, at Beauly, he stopped and diverted his troops to the Catle Downie and then went from there on to Inverness. He planted his standard in the Highland Capital and summoned all the fighting men of Ross to his banner. And they readily took up his cause and joined him. Instead of staying and defending what he had gained, Donald marched on toward the east in the hopes of raising even more troops on his way. He knew that eventually the Duke of Albany would meet him with his own forces, and he had threatened to burn down Abardeen and this may have been another reason for marching in that direction. When the people of Aberdeen learned that he and his 10,000 troops were marching in their direction with the intent to burn it down, they would have been thrown into a panic.
Eventually, Donald MacDonald arrived at Harlow and was met by his cousin the Earl of Mar. The men of Abardeen assembled under the leadership of the Earl of Mar. The Earl of Mar marched by Inverury and sighted the enemy near the village of Harlow, about ten miles from Abardeen.
The two forces met in bloody and fierce battle and fought all day and did not cease fighting until darkness fell, The force commanded by Mar had been annihilated. The Scottish version of what happened was that Donald retreated from his fear of this army he had just defeated, which makes no sense. Some writers believe that he had expected to have reinforcement from the English. But if he had, he now knew that it was not coming. With all of the Lowlanders now against him, he would have been aware of how difficult it would be to keep the forces which he had gathered from scattering and dispersing for a very long time, and he most likely felt it prudent to return to his own Island stronghold, instead of waiting for or pursuing further conflict with the Duke of Albany.
When the Duke of Albany heard of the defeat at Harlow he hastened to Ross and went to Dingwall and took possession of the castle and established his own authority through Ross, displacing any authority that Donald may have gained. Donald's domain on the Island was impenetrable because his fleets were superior to the Scottish fleet. The Duke of Albany knew that there was only one place where Donald was vulnerable, at his mainland holding of Argyll. He took an army there in order to attack it. Donald, however was able to repel him and the Duke did not succeed in humbling him.
Archibald MacDonald says that John of Fordun recorded that Donald made a treaty with the Duke of Albany and submitted himself to be a vassal and gave hostages to ensure it. He also says that no record of this is in the national records and no other chronicler of the time mentions it. There are records that show that Albany made a campaign against Donald but none that show this treaty. There is record of the Duke complaining because he had not been reimbursed for his expenses. Although Donald did not succeed in his attempt for the earldom of Ross, he remained unaffected in his own island principality.
Donald MacDonald is said to have joined a religious order and spent his last years in religious duty, dying about 1423. He was buried at Iona.
The clan Donald
By Archibald Macdonald - 1896
History of the Macdonalds and Lords of the Isles: with genealogies ... -
by Alexander Mackenzie - 1881