I had to rewatch all of the episodes with MrKnopeWaffle, who wanted to get into the series with me. I’ve noticed a couple of things.
First, in the narration from The Headless Warden, he kept referring to “what WE did.” So we know he didn’t act alone.
When Henry’s Dad has Henry out in the woods he asks him “do you hear it now?” DevilBoy asks him the same thing after he asks how old he is. This makes me think that Henry was being used or was used to help trap DevilBoy to begin with? Or was going to be used to get rid of him and couldn’t?
When Jackie Torrance mentions Henry’s disappearance while talking to Henry, she mentions the storm that hit, “Guinness Record” stuff, and I thought about Storm of the Century and the couple that gave their son to the devil guy to make the storm go away. My memory is rusty on the players and I’m not equipped to multiple screen google at the moment. I am thinking DevilBoy might be a little too young to be that kid all grown and sent out in the world to cause shenanigans, but maybe not?