I didn't want to say anything yet, but I had overheard some of the townspeople talking and it didn't exactly seem like they were very confident in Jack.
"He's pretty nonchalant about this..." Clown said to the person sitting next to him. "I mean, when Oogie was Pumpkin King this kind of thing never happened. Sure, he might not have been very nice to us, but if humans came waltzing in here he'd show them who's boss."
I thought about that. Fighting skills didn't exactly seem to be a strong point of Jack's, and maybe it was something that was slightly essential to being a good ruler. But we weren't trying to do anything bad. So why did it matter?

"Remind me ONE more time: WHY are we on this SUICIDE mission?"
"I've already told you five times!"
"Oh, yeah. We're fighting Oogie to show the town that I'm a better leader."
"That's RIGHT, Jack," I said with mock-praise. "Someone should give you a prize." He scowled at me.
When we finally got to Oogie's house, Callie bravely volunteered to go in first, but we ALL wanted to go first. When we were arguing over it, Callie shoved me with a little too much force and we all toppled into eachother and fell down the hole and into Oogie's casino.
Hey, not exactly a graceful entrance, but we did it.
"Ow, your foot is in my eye," Callie whined at Jack.
We all stood up and looked around in that way most heroic heros do. And in the way most villainy villains do, Oogie laughed at us from the other corner of the room, where he had been the whole time.
"Hey, Jack, long time no see," He said with an evil grin. "Don't tell me-- You brought these pathetic wimps here to help you?"
"ALRIGHT!" I interrupted loudly. Oogie paused for a second, taken aback that someone as "wimpy" as me would yell at him. "I'm the referee in this fight! The rules are--"
"But we don't NEED rules to fight eachother!" Oogie protested.
"THE RULES," I repeated, glaring at Oogie, who decided it best not to question me, "are simple. No weapons. To defeat your opponent, knock him to the ground and keep him there for 10 seconds. Do I make myself clear?"
"But..." Oogie began.
"DO I MAKE MYSELF CLEAR?!?!" I screamed. Oogie quickly nodded.
"Ready....GO!!!"
The fight didn't last 30 seconds. Needless to say, Oogie had no problem knocking Jack flat on the groung by kicking him in the back of the knees and then keeping him there by standing on him. It was the most pathetic thing I had ever seen.
"JACK!" I yelled, thoroughly disappointed. "I expected you to last longer than THAT!!! What's wrong with you?!"
"Sorry," he mumbled, getting up and dusting himself off. Oogie was doubled over with laughter on the other side of the room, unable to say anything.
When he finally caught his breath, he managed to gasp, "Jack! You MORON! HAHAHA! Do you realize what I just did?!"
No response.
"I just BEAT you in a FIGHT!" Oogie said smugly. "Which means...I'M the Pumpkin King now!"
"WHAT?!" Callie blurted. "THAT'S NOT FAIR!"
"Yeah!" Jack agreed. "You can't just take my position because you stood on me for 10 seconds!"
"Oh yes I CAN," Oogie retorted. "It's the RULES. Look it up."
Oogie handed us The Official Law and Code of Halloween Town and we looked it up. we found the page pretaining to the Pumpkin King title, and read it. Towards the very bottom it said: "Anyone who beats the current Pumpkin King in a fight of any kind, whether by challenging or by being challenged, is then allowed the title of Pumpkin King along with any possesions the previous Pumpkin King may have had."
Oogie laughed even harder when he saw the shocked and disappointed looks on our faces.
"HAHAHAHA!!! You should have thought about that before you came here, idiots!"

And so, Jack was left without ANYTHING. Pretty much all he had was his clothes and Zero. And it just so happened to be raining pretty heavily that night.
The three of us and Zero sat on a street corner, miserable and soaking wet, with nothing to look forward to but more rain pouring down on us. None of us said anything for a long time.
"Sorry, Jack," I said, breaking the silence. "If I wouldn't have come up with that stupid plan, none of this would have happened."
"That's okay," Jack replied glumly. "It was bound to happen eventually anyway."
Water splashed me in the face from a foot in a puddle, and when I had wiped it out of my eyes I saw Oogie standing in front of us bearing a particularly nasty grin.
"What the hell do you want!?" I yelled, feeling that we had dealt with him enough for one day.
"Oh, nothin' much," He replied. "Just thought I'd see how you were doing. BAHAHAHAHAHA!!!"
I glared at him.
"Since you're the loser, Jack, I thought I'd tell you something to make you feel better." Jack glanced angrily in Oogie's direction but pretended not to be listening.
"I was the one who teleported these humans here. It was all part of my extremely feindishly clever plan to get the town to stop trusting you so that I could become the Pumpkin King. Your little human sidekicks made it SO much easier, though! Thanks a ton for that!"
Jack was still pretending not to care, but with Oogie's last comment it was getting increasingly hard not to listen.
"And the show's not over yet," Oogie continued in a low voice. He bent over so that he was at eye level with Jack. "You thought I'd stop at Halloween Town, did you? Well that's TOO BAD...because I'm gonna take over the WHOLE WORLD!!! MUAHAHAHAHAHAHA!!!" He walked off, laughing to himself.
"Okay," I said, confused, "what's this about taking over the whole world?"