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In "The Nightmare Before Christmas," Jack wants to take over Christmas and bring a wonderful, joyous holiday to all the people of the "real world".

He's been to Christmas town, and he's seen what the gifts should be.

But, the citizens of Halloween Town obviously can't quite grasp the concept of thoughtful, sweet and fun gifts... instead they make terrifying toys for the children, because that's all they know.

How can Jack even allow these toys to be delivered? Let alone, be the one to deliver them, when he so desperately wants to recreate the perfect Christmas for his own town.

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    Lack of sufficient oversight? His workers clearly don't get it, and most of the "unreasonable" gifts were wrapped behind his back (not maliciously, mind, he just didn't notice those ones). Since he then didn't unwwrap them...
    – Clockwork-Muse
    Dec 13, 2014 at 14:00
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    A major element of the whole story is that Jack, himself, doesn't get Christmas. This is doubly true for the residents of Halloweentown. What they all, including Jack, like or find cute isn't in line with what children do.
    – phantom42
    Dec 13, 2014 at 15:31

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To accompany the film, Touchstone Studio also licensed a 'Penguin Active Reader' book for younger viewers. This book was based on the Tim Burton screenplay and can, presumably be considered canon to the main film:

To answer your question, the simple fact is that Jack was blissfully unaware of the nature of the presents he was delivering.

  • He didn't inspect them before they were loaded into the bag:

In Halloweentown, the vampires finished making Christmas lights— with little skeleton heads. The youngest witches finished making their toys—wonderfully dangerous toys. Jack's plans for Christmas, the most important thing in his life, were almost ready. But he didn't look at the lights and the toys before they went into the bags.

  • He didn't wait around to see the presents being opened

He stopped his sleigh at each house and put pretty presents under each Christmas tree. In one house, a little boy came down the stairs and watched him. When Jack turned away from the Christmas tree, he saw the young child. "Here, little boy! A present from Santa!" said Jack. And he gave the boy a present.

Jack had to go to the next house. He couldn't wait and watch the boys face. But when the child opened the present, he didn't smile. His face went white and his mouth fell open. He screamed wildly.
Jack heard the boys screams and he smiled. "He likes it," Jack thought. "Nobody is scared of me and I'm making everybody happy!"

  • Mistaking the scream of terror for screams of joy (a natural mistake for the King of Halloween), Jack genuinely believes that he's doing a good job

There was only one happy face in town. High above the police station in a strange sleigh, a skeleton's smile shone. Inside his head were pictures of happy children's faces. He had no idea about the problems below.

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    Jack did, however, suggest using a bat for a hat as opposed to a piece of roadkill. So that suggests that he at least thinks that Halloween-themed gifts are okay. The bat itself wasn't dangerous (it was dead right?), but it was un-Christmasy and Jack never realized. He also loved the skeleton raindeer he gets from the scientist; and never mentioned that they should be better. But that may be his personal opinion since he himself is a skeleton.
    – Flater
    Jan 27, 2017 at 16:07
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As explained, Jack does not truly gets Christmas. Furthermore, even if he saw gifts from Christmas Town, he might just have noticed they are small objects, with fun colors, and which are childish. Nevertheless, as we can see at the beginning, Halloween people are really enjoying frightening things and they are having fun with the creepiest jokes, so they did it as well and it did not surprise Jack at first. That's why he only understands his mistake after he has been taken down by the army (graveyard scene/song "what have I done" <- means "now I realize I did not do it well)

Jack might also have convinced himself while telling Santa is a terrible guy, and thinks to understand that this big boy might like "Halloween Style Xmas"

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  • I would add that Jack got too carried away with his idea of Christmas. In his excitement, he probably tricked himself into believing what he was doing was "giving Santa a year off", because he's always friendly to Santa and never had a malevolent intention. Maybe he assumed Santa to have the same ennui about Christmas that Jack felt about Halloween? Jack also never assumed Santa is a terrible guy. That is to say, Jack doesn't say Santa is inadequate at his job (terrible Santa); but he does perceive Santa as Sandy Claws (a terrible ruler, but that's a compliment from Jack's Halloween POV).
    – Flater
    Oct 26, 2015 at 15:39

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