After his allies Cletus Ganderfald and Bapheloctis were defeated by Karen Wilder, Damien Mortis pressed his own challenge to avenge their losses. Damien and Karen have met each other in the ring in the past, thus it was no surprise when the Overlord elected to have the Baron tested. However, the events that followed were a surprise.
After Cassius Maximius was selected by the Overlord, Skyler Chamberland was selected by Damien to duel. But the Baron of New Haven, Rakeesh, did not want Skyler to duel and used the rights of a Renegade Baron to insert himself as Damien's defender. While this may not have set well with Damien, the outcome did as Rakeesh was able to dispatch of Cassius and clear the way for Damien to meet Karen.
Damien made the most of his opportunity and defeated Karen in a close twelve round duel. This already unusual challenge became more interesting following the match when Baron Rakeesh accused the new Overlord, and Skyler and being criminals. Rakeesh said that he stepped in on Damien's behalf to prevent Skyler from winning a Barony should he and Damien prevail. But once Damien did win, he announced his intent to challenge the Overlord to correct the wrong he had helped to bring about. Rakeesh never wanted Damien to become Overlord and made it his goal to remove him.
In response, Damien and Baron Bapheloctis offered a gold bounty to whoever could defeat Rakeesh in a Baronial challenge. In the days that followed Baron Ekthbjlgke Smith also announced his intent to challenge Damien. At this announcement, Rakeesh offered to step aside and allow E the first challenge against the Overlord.
Ironically, it was Cassius Maximius who eventually defeated Rakeesh before he could make any challenge to the Overlord as the Baron of New Haven.
However, Baron E did make good on his intent and issued challenge to Damien shortly after.
Odds makers favored the Overlord to test the Baron, however when the time came, Damien was quite pleased to take on the Baron himself. In two lopsided duels, Damien was able to defend his title from the Baron's challenge. Damien won both duels five to one, with one lasting nine rounds, and the other eight. Amusingly, Damien named Cassius Maximius his lady of honor prior to the match.
Damien's second challenge came from the spring 2006 Warlord tournament winner, Skyler Chamberland. Damien met the challenger in a single match that was tied at four after eight rounds. One round later, Damien's quick strike over Skyler's low attack secured the victory and Damien's title.
Johnathan Ecorian Havoick was next to challenge Damien for the mantle. While he did not doubt Damien's skill, Cory challenged on the basis that Damien was not a constant presence in the Arena and done little to progress the sport. On the night of the challenge, Damien pulled out all the stops in an attempt to progress his own reign. Damien asked Baron of the Old Market District, Bapheloctis, to issue a Test of Worthiness to the challenging Warlord. In an attempt to defend the Warlord's right to challenge, Baron of New Haven, Cassius Maximius, stepped forward to meet Baphe.
In nine short rounds, Baphe dispatched of Cassius by a score of five to two. Cory then stepped into the ring and appeared to be headed in the same direction as Cassius. By round seven, the score was three to one in Baphe's favor. But over the next eight rounds, Cory scored four unanswered points to defeat Baphe and get his match with the Overlord.
The match with Damien was quick, but very tense. For the first six rounds, Cory would take the lead, and Damien would immediately tie the score in the following round. It wasn't until round eight that Cory was able to score a two point lead, and with that lead came the victory. With a score of five to three, Cory ended Damien's reign.