I did have this theory that Dirk thinks he will be a character who's above the rest of them, but he's actually setting himself up to be like Caliborn and become the "big evil bad guy" that they all have to defeat in the end. The way to win the game is to actually beat the fuck out of the guy who made you play the game to begin with. The OG cast of Homestuck never actually got a chance to beat the fuck out of Hussie and make him stop lol (besides Vriska) but Dirk is a character that they can actually stop. That, and the OG characters never really had a chance to stop the horrible cycle of abuse in their childhoods. Dave never won against his brother, Rose never actually reconciled with her mom, Jade never got to be raised by her grandpa and learn the truth of his death until years later, and John never got over the death of his father after playing the game and "winning".

The new kids however have a whole new chance to get away from all of the toxic cycle AND break it (by beating the fuck out of Dirk Strider)