Eleven

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For precautions, Sam and Dean used their handcuffs and cuffed Jack's hands to his back to keep him from trying to escape as they put him back in the car and headed back to the bunker.

When they arrived at the bunker, Sam and Dean then took Jack into the bathroom, where they had him sit down on the floor while they put the handcuffs around the pipe of the bathroom sink and cuffed him back up.

"What? This is it?" Jack asked. "This is your brilliant way of keeping me secured in this place?"
"It's to keep you from escaping and to keep you from doing any damage to yourself." Sam said.
"What makes you think I won't be doing things to myself in here?" Jack asked.
"Which is why Sammy here is going to look after you." Dean said.
"And what about eating?" Jack asked.
"We'll give you food." Sam answered.
"What if I have to pee?" Jack asked.
"That's for you to decide!" Dean answered.

Dean then clutched the doorknob and looked at Sam.

"You sure you got this?" Dean asked.
"Definitely." Sam assured.

Dean then closed the door and Sam locked it before watching Jack.

Jack put his head against the sink, then out of nowhere started banging his head against it harder and harder.

"Jack! Stop it!" Sam said running over and stopping him.
"Why? I can just easily bang my head against the sink, get brain damage and die!" Jack exclaimed.
"Jack, this isn't you talking!" Sam explained. "Your entire soul is almost gone and this is why you're going insane and talking and doing things like this. Dean and Cas are trying to figure out a way to get your soul back to normal somehow. We'll figure it out, we always do."
"And what if they don't?" Jack asked.
"Then we have to go with plan B and make you soulless..." Sam said.
"I'm not going soulless, Sam..." Jack claimed.
"At this point, it's honestly better than you going insane and wanting to kill yourself." Sam assured.
"I don't want to not give a damn about anything!" Jack exclaimed. "It's like being Anti-Jack..."
"Except without the killing..." Sam said.
"I could end up killing people, who the hell knows?" Jack asked.

Sam looked down and sighed.

"Alright... Here's the deal... If we can't figure out a way to get your soul back, then we'll let you go." Sam said. "We will be done taking care of you and you can just do whatever the hell you want."
"What about Dean and Castiel?" Jack asked. "What will they do?"
"I'll try and convince them to do it as well..." Sam said.

Jack sighed and then nodded. The deal was on.
---
Back at the table, Dean and Castiel were arguing.

"His soul cannot magically be repaired, Dean..." Castiel said.
"Not perfectly repaired as if this never happened..." Dean said. "Just a bunch of barriers like Death did on Sam when he was soulless..."
"Dean, Death has been done taking orders from you and Sam!" Castiel explained.
"It's not like we're asking for our souls to be repaired, it's somebody else's!" Dean argued.
"It won't matter!" Castiel responded.
"Then we bribe him with some deep dish pizza and a mega soda from Chicago!" Dean exclaimed. "He loved that place!"
"We're not bribing him, Dean..." Castiel said.
"Well what in the hell can we do at this point, Cas?" Dean asked. "Don't you have anything in there that can at least stop Jack from his insanity?"

Castiel's eyes widened, realizing something.

"Crowley..." Castiel mumbled.
"Crowley?" Dean asked.
"He's alive..." Castiel stated.
"Well we'll worry about Crowley later!" Dean insisted.
"Dean, Crowley is the key to possibly retrieving parts of Jack's soul back..." Castiel claimed.
"But he basically destroyed Jack's soul!" Dean said.
"It was Jack coming back to his senses that destroyed his soul, not Crowley..." Castiel explained. "But Crowley was the one who turned his soul into something evil. If he could change his soul evil, he could possibly change it back."
"Dude, Crowley's the king of Hell!" Dean exclaimed. "Anything the dude touches either turns evil or dies! There's no way he can just magically bring a soul back!"
"He can't bring a soul back, but he can possibly fix it..." Castiel claimed.
"What makes you think he would want to after what Jack did to him?" Dean asked. "He could want revenge!"
"Well, if what Crowley said is true, and if Jack is the future king of hell and Crowley's actual son, he would most likely try and treat him like one." Castiel explained.

Dean paused to think for a moment before looking at Castiel.

"I guess we could try..." Dean sighed. "But if this all goes horribly wrong, you will pay."
"Sounds fair..." Castiel nodded.
---
Back in the bathroom, Sam is watching as Jack fell asleep, his head leaning against the sink again, the only place he could properly rest his head comfortably.

Sam jolted a little as the door slowly opened. Dean was on the other side.

"You good enough to be out here for a minute?" Dean whispered.

Sam nodded and he quickly and quietly stepped out of the bathroom and into the hallway.

"What's up?" Sam asked.
"I think we've got a plan." Dean said. "Cas says that we can go back to Crowley and get at least some parts of his soul back."
"He's alive?" Sam asked.
"Yeah..." Dean nodded. "And Cas believes that since Jack is apparently Crowley's son, Crowley will do whatever he wants him to do for him."
"Really?" Sam asked. "Shouldn't it be the other way around?"
"Well since Jack is going to be the future King of Hell and Crowley's only living son now, I guess he's treating him like a spoiled brat..." Dean said.
"O-Okay..." Sam nodded. "So we just take Jack back to Crowley and he asks to fix his soul and Crowley will just do it?"
"Apparently!" Dean said.
"Alright, then let's do it..." Sam said.

Sam and Dean then opened the door to the bathroom, only to find no sign of Jack anywhere.

Dean went over to the handcuffs which were now on the floor and covered in blood.

"Dammit..." Dean whispered under his breath.
"How the hell did he get out?" Sam asked.
"Well he obviously used his own skin from the sharp edges of the cuffs to bleed and slide his way out." Dean explained. "Then he crawled out the small window in the corner of the room there."
"How's he able to get through there?" Sam asked.
"Well he's a tiny fricken leprechaun compared to us!" Dean said.
"Obviously!" Sam exclaimed.

Sam noticed a note on the corner of the window. He read it.

I'm not going there. I'm sorry

Jack

"Crap, he heard us!" Dean exclaimed.
"We gotta go and find him..." Sam said.
"No kidding!" Dean said.

Sam and Dean went to get Cas and head back into town to find Jack again.

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