John MacDonald II, Lord of the Isles, lived from 1434 to 1503, and is also known as John of Islay, Earl of Ross. John was the fourth, and final, Lord of the Isles to hold the title in its own right, and many view him as the man whose political miscalculations threw away the enormous gains made by Clan MacDonald since the days of Somerled. The wider picture in Scotland at the time is set out in our Historical Timeline.
John was the son of Alexander of Islay, Earl of Ross and Lord of the Isles, and Elizabeth, daughter of Alexander Seton the lord of Gordon and Huntly. He succeeded to his father's lordship in 1449 while still a minor. He is usually referred to as John MacDonald II, Lord of the Isles to avoid confusion with the first Lord of the Isles, John of Islay.
The seeds of John's downfall were sown very shortly after he inherited his titles, when he married Elizabeth Livingstone, the daughter of Sir James Livingstone. It is said John entered into this very unhappy marriage in return for unspecified promised made to him by James II. Sir James was a powerful politician during the minority of James II, but not a man of great wealth or estates, and as a result a man whose power and influence might only be transient.
And so it proved. Sir James fell from favour with the King in the very early 1450s and sought refuge with his son-in-law, the young Lord of the Isles. James IIs' promises to John at the time of the marriage were never kept, and John rose in revolt against the King, leading an army that took control of the castles at Inverness, Ruthven and Urquhart. He also formed an alliance against James II with William Douglas, 8th Earl of Douglas, the most powerful nobleman in southern Scotland at the time.
James II's response was to try to persuade the 8th Earl of Douglas to withdraw from his alliance with John MacDonald II (and others) against the Crown. When the Earl refused to do so at a meeting between the two on 22 February 1452 in Stirling Castle, the King personally murdered him. John subsequently stood by as James II systematically wiped out the House of Douglas in the years up to 1455, even benefitting by acquiring some of the Douglas lands seized in the Borders. James II died in 1460, leaving John in a strong position, having successfully survived challenging the King and having extended both his estates and his influence.
On 4 March 1461 Henry VI of England was deposed by Edward IV, fleeing into exile in Scotland where he received considerable support from the new Scottish King, James III. In a blatant effort to stir up trouble in Scotland for James III, Edward IV sent an envoy to seek the support of John MacDonald II, Lord of the Isles. The outcome, in February 1462, was the Treaty of Westminster-Ardtornish, under which John agreed to pay homage to Edward in return for English help in gaining control of all of Scotland north of the Forth.
The nature of this English "help" was left vague, but despite this, John proceeded to raise an army which marched on Inverness, under the command of Angus Óg, John's illegitimate son. James III responded by dropping his support for Henry VI, so preventing a war with Edward IV's England. And John MacDonald II, finally realising how one-sided his treaty with Edward IV had been, withdrew back to his island strongholds.
In the mid 1470s the English revealed the full terms of the Treaty of Westminster-Ardtornish to James III. John MacDonald II was stripped of large parts of his land and a number of his titles, and though he retained the title of Lord of the Isles it was no longer to be inherited, in future its holder being determined by the Scottish Crown. In the face of this huge loss of prestige, John was overthrown as chief of Clan Donald in a coup mounted by his son Angus Óg, and was subsequently defeated by him at the Battle of Bloody Bay, off Tobermory, probably in 1480.
John tried to reassert his power after the murder of Angus Óg in 1490. But his efforts to regain the Earldom of Ross, were fought off by the Mackenzies. And in 1493, James IV finally gave up on John as a force capable of controlling western Scotland and stripped him of the title of Lord of the Isles. John lived out his days in lowland Scotland on a royal pension. He died in Dundee in 1503, and was probably buried at Scone.