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I like to imagine he's a REALLY adorable villager- if he showed his face he would be too cute to be doing anything for halloween- like idk a hamster or something. But that's just me. xD
I think Jack "Czar of Halloween" is most likely a ghost or maybe wields magical powers kind of like Katrina. Katrina is psychic but Jack has teleportation powers and can cast curses on you. Destroys your clothes and transforms your items into spooky stuff...magician maybe? The ultimate prankster who's better than Blanca?
Oh and I have a theory about something off topic. You remember back in the original Animal Crossing on the GameCube where you meet Wisp at night and than he tells you that if you don't catch all 5 sprites in time then his "Master" will punish him. I think Wisp's master is Jack. I mean think about it...Jack stands before you with an official status that he has givin to himself. If you don't give him his candy than he will punish you...just like how the "Master" will punish Wisp...