A dispute occurred in 1530, when Sir Robert Charteris, the 8th Laird and chief of Clan Charteris fought a duel with Sir James Douglas of Drumlanrig in what was said to have been one of the last great chivalric contests. It was fought with all the observance of a medieval tournament with heralds and the king himself watching from the castle walls. The joust was apparently fought with such fury that Charteris' sword was broken and the king had to send his men-at-arms to part the combatants.