The Masked Man is, according to at least one member of Mythic Quest Studios' upper management, "everyone's favorite NPC". Normally benevolent, and therefore an NPC players would naturally approach, the NPC was a perfect target for a hacker intent on doing harm to the game.
Hacked by Pootie Shoe, it threatened every player's financial details, and thus the very existence of MQ itself. Beyond that, Pootie's use of the NPC could well have brought down the game mechanics. He used the Masked Man to randomly give the most expensive of in-game loot to players — and sometimes to kill them.
As hacked, the Masked Man was originally a source of extreme consternation to Poppy — so much that she got stress hives. At first, this condition wasn't alleviated by Ian's reaction to the situation. As he searched for a solution, he advocated completely contradictory plans to deal with the rogue NPC. This lunacy, and therefore the Masked Man himself, drove Poppy to accept a job elsewhere.
However, when Ian decided to challenge the Masked Man to single combat, she chose to lean in to the lunacy. Though superficially crazy, the plan had the virtue of drawing the Masked Man out — something that allowed Poppy to do an IP trace to expose the hacker.
Just as Ian prevailed in the ultimately vanilla style competition, Poppy was able to hack into Pootie's computer, turn on its webcam, and expose the true identity of the Masked Man.