In 1488 the Clan Montgomery burned down the Clan Cunningham's Kerelaw Castle. This was part of a century-long feud that had apparently started when the office of Baillie in Cuninghame, held by the Cunninghams, was awarded to the son of Lord Montgomerie on 31 January 1448-9. The two clans had been on opposing sides at the Battle of Sauchieburn, with Hugh Montgomery among the victorious rebels, and Alexander Cunningham, 1st Earl of Glencairn slain with the defeated James III. A longstanding rivalry (principally over the Bailieship of Cunninghame) was now a vendetta.