John of Islay, Earl of Ross

John of Islay (or John MacDonald) (1434–1503), Earl of Ross, fourth (and last) Lord of the Isles, and Mac Domhnaill (chief of Clan Donald), was a pivotal figure in late medieval Scotland: specifically in the struggle for power with James Stewart, James III of Scotland, in the remoter formerly Norse-dominated regions of the kingdom.

Thereafter and until his death in 1503 John remained an inconsequential figure while, until his murder in 1490, Angus continued to dominate the affairs of Clan Donald.

John's marriage to Elizabeth Livingstone had been determined by the usual calculations of profit and position, as were those of other important people of the time.

John at once rose in revolt, taking the royal castles of Inverness, Urquhart and Ruthven, perhaps less to show his support for the Livingstones than to remind the king of his own power in the north.

This revolt of the Lord of the Isles came at a dangerous time for the king, who was involved in a virtual civil war with the Earl of Douglas, the most powerful noble in southern Scotland.

John showed little concern for the fate of his ally, especially as James effectively turned a blind eye to the occupation of the northern castles.

His relations with the crown continued to improve and he did nothing to prevent the final destruction of the house of Douglas in 1455, even obtaining title to some of their border estates.

In February 1462 John's representatives concluded an agreement once referred to as the Treaty of Westminster-Ardtornish, that envisaged nothing less than the conquest and partition of Scotland.

He achieved maximum results at minimum expense, laying out only as much bait as necessary to create a political disturbance in northern Scotland.

It most certainly had the effect Edward desired; for the Scottish government, faced with rebellion in the north, and fearful of attack in the south, dropped the politically embarrassing Lancastrian connection.

In the mid-1470s Edward, preparing for a war with France, and anxious for good relations with Scotland, finally revealed the full terms of the Westminster treaty.

The Lordship had always depended on territorial expansion to give life to its warrior values; but now that it was contracting all of the latent tensions came forth, finding expression in the person of Angus Óg.

Angus, according to Hugh Macdonald, ejected John both from the leadership of the clan and from his own home, forcing him to seek shelter under an old boat, and precipitating a bitter civil war.

[4] John managed to raise an army of his own against his son, and his fleet of galleys met those of Angus sometime in the early 1480s – we cannot be more precise than that – off the coast of Mull to the north-west of the present town of Tobermory, an area ever afterwards to be known as Bloody Bay.

[7] With the death of Angus, John re-emerged from the shadows, but his "feebleness of character and the lawlessness of his chieftains" led him to bestow lordship of the Isles on his nephew, Alexander Lochalsh.

[16] He started his rule as a lion and ended as a sheep[citation needed], having in the process alienated almost everyone, including the closest members of his family.