The Better Boogieman
I was just contemplating Evil!Boogieman!Jack from an alternate universe playing Pitch's role with Pitch either not existing or taking the role of the winter spirit. Then I contemplated on what would happen if this Alternate!Jack and Canon!Pitch met. I think they would face off to decide who the better Boogieman is. Jack wins of course.
My reasoning behind it is that Jack would be a more effective Boogieman because he is still technically a child, just immortal. There is a phrase out there, though I don't remember exactly how it goes, that says something like "There is nothing more cruel than a child". Children are selfish, greedy, and don't understand limitations. They'll take what they want, even if it makes another child cry, and aren't afraid to take stupid risks because they feel infallible. Children also aren't afraid of hurting feelings or dealing low blows. They are also terribly easy to frighten because they can be highly empathetic and have very active imaginations. Children honestly believe anything is possible and that gives Jack all the more power because he himself would not acknowledge limitations unless he was literally slapped in the face with one.
Although I think he'd be especially frightening because he has all these qualities due to being stuck in a permanently young state, but would also have all the knowledge, experience, and power that comes with being an immortal supernatural being. So he may be childish and not acknowledge limitations until he's face to face with one, but while a child would sit and cry until an adult fixes it, Jack has the cunning and power to overcome or even destroy the obstacle in question. If someone stands in the way of what he wants he can tear them apart. Imagine someone who has not yet really moved beyond the self-centered stage of development, with all the qualities that would entail, that has such terrifying power.
Pitch is an adult. He's logical, practical, and is much better with planning and tactical maneovering than Jack would be. But think about all the limitations that adults put on themselves because they "know better". In growing up we gain power in many ways, but we lose freedom in many others. We tend to become less imaginative, more set in our ways. Pitch will have the advantage over Jack in many ways, but Jack has the uncontrollable quality of still being a child in the way he thinks, and thus all the freedom that a child would have because children "don't know better yet".
I don't know if anything I'm saying makes any sense and I have gone on rambling about it for way too long. Please drop a comment and tell me what you think of my theory. I'm open to being informed of any holes in my logic and any one else's opinion on the matter.
Thanks for listening!
Edit: Got a new scanner so I re-uploaded the pic.