Sorry Guybrush, if we're talking a straight up fight in an arena, your organs will be strewn across the ground in 5 minutes or less (see: Demon Peepers).
Now, if we're talking tactical battle with hiding places and items, Guybrush has a chance. Max isn't stupid- he's certainly mentally unstable but NOT stupid (see They Stole Max's Bran, Egypt section, where it's essentially Max being rational and in control)- but he has nothing on Guybrush's level of sheer ingenuity.
I am a community moderator, here to assist, keep the peace, and keep these boards clean and friendly for all. I am a volunteer, and not a Telltale employee, and my opinions are my own.
--Playin' poker with GLaDOS before it was cool--