Grayson MacLeod's reign as Overlord began when he challenged and defeated Damien Mortis. With the help of former Overlord Max Blue, Grayson was able to overcome a test of worthiness administered by another former Overlord, Cletus Ganderfald. After his victory, Grayson's first order of business was to award the vacant Barony of Dockside to his champion, Max.
Unfortunately for Grayson, that was one of his only acts as Overlord. Not long after, the winner of the summer 2005 Warlord Tournament, Rena Cronin, took her shot at becoming the Supreme Duelist of the Duel of Swords. Grayson was able to take first blood in the single duel bout, but was unable to hold or regain the lead after that. With a five to four victory in nine rounds, Rena was able to put a quick end to Grayson's reign.