After defeating Baron Bapheloctis in the Test of Worthiness, a feat champion Cassius Maximius could not accomplish, Johnathan Ecorian Havoick defeated Damien Mortis to become the Seventieth Overlord of the Duel of Swords.
Cory's first challenge came from the summer 2006 Warlord Tournament winner, Skyler Chamberland. Skyler's win in the tournament marked his second consecutive first place finish. However, as is often the case with Warlord Tournament winners, Skyler's momentum couldn't last the two weeks between the tournament and the challenge. In a quick seven round duel, Cory dominated his challenger with a final score of five to one.
After a long layoff without a challenge, Cory was again challenged by a Warlord Tournament winner. However, for the first time in nearly half a year, that winner was not Skyler. Instead, Spike u'Shell battled her way through her fellow Warlords to claim the intercession free challenge in the fall 2006 tournament. Cory elected to use the best-of-three format, and he was again dominant against the tournament winner. In duels of eleven and twelve rounds, Cory secured two consecutive five-to-two-point-five victories to retain his title.
Vanion Shadowcast's challenge marked the third straight challenge to Cory brought by winners of Warlord tournaments. Vanion claimed victory in the winter 2007 tournament. But just as he did was the past two winners, Cory once again proved his dominance against Warlords. Cory scored four unanswered points to claim the five to one, seven round victory.
Only days after his defense over Vanion, Cory was challenge by Baron Anjolie Quinn. This challenge came as a surprise to many in the community as the two were reportedly husband and wife.
In one of the more stranger challenges the Arena had seen in recent years, The Baroness of the Old Market District, Anjolie Quinn, challenged her husband, Cory, for the crown of Overlord. The real intent behind the challenge was never made fully public; however the rumors that ranged included marital difficulties between the two to a desire for Anjolie to test herself against her husband.
After some speculation about weather or not Cory would test his wife, he eventually opted to settle the challenge in a single duel format. Just like in his other challenges, a strong lead was taken right at the onset of the duel. Unfortunately for Cory, that lead was Anjolie's. After nine quick rounds, Anjolie had defeated her husband, five to one.
Following the match, Cory announced that he would remain renegade to his wife, further fanning the rumor mill as to the state of their marriage.