He was most often known as James M'Connall from the Gaelic pronunciation of the name Mac Dhòmhnaill, the modern Macdonald spelling being the anglicization of the name.
At the Battle of Traigh Ghruinneart on the Isle of Islay in 1598, he led forces against Sir Lachlan Mor MacLean, 14th Chief of Duart.
[1] He then fought Hector Og Maclean, 15th Chief who sought revenge for the death of his father in the Battle of Benbigrie.
[2][3] Following the Battle of Benbigrie, James fled to Ireland; returning to Scotland, he was captured by the Earl of Argyll and subsequently imprisoned in Edinburgh Castle from 1604 to 1615.
[4] In the spring of 1615, James escaped captivity and led a force to recapture Dunyveg Castle from Sir John Campbell of Cawdor in June, holding it until the castle was recaptured by a force under the Earl of Argyll in October.