[1] Upon the death of Robert I of Scotland in 1329, he accompanied Sir James Douglas with a retinue of Scottish nobles on crusade.
The party stopped first at Sluys, Flanders, where confirmation was received that Alfonso XI of Castile was preparing a crusading campaign against the Muslims of the kingdom of Granada.
The Scots sailed on to Seville, Spain to meet Alfonso XI and pledge their support.
He was one of the few survivors of Douglas's party of knights and men-at-arms who survived the siege and battle of Teba, not being able to take part in the skirmish, after suffering a broken arm.
In 1334, he captured the English nobleman Richard Talbot, an ally of Edward Balliol, as he was attempting to pass into England from the north.