4.16 On the Head of a Pin is the episode this takes place in.


When Angels Fail Us

"…I'm just- I'm just getting tired of burying friends."

"Well, get angry."

Dean snorted, turning to look out the window. He wasn't driving, for once. After the funeral, all his remaining energy had just sort of waned, and he had passed the keys to his brother. His brother who was talking about Ruby, and leads, and he wanted to slap the stupid out of Sam. They had just buried their friend and Sam was talking about that demon bitch.

In the backseat, his wife was asleep, curled up in his leather jacket and using a duffel bag as a pillow, her long legs tucked awkwardly up against her stomach in a sideways kneeling position. She had known Pam better than them, she had spent a month with Pam, and in that time, they had gone past the mentor/student role and become friends.

Pamela and Jane… Dean closed his eyes, recalling what Pamela had said to Jane before dying. "Don't let this be you", "it could be you", and Pam had been right. It could be Jane. He had never been oblivious to the dangers of the job, or the fact that Jane wasn't as seasoned as the rest of them were. Hell, she had been in some serious shit a time or two, and he had panicked then. But still… now, he overlooked it, because he had confidence in his ability to keep her safe. But how could he keep her safe, when he couldn't even keep other people safe? People like Pam?

It could have been her. Maybe, that was his biggest issue right now. He was grieving for Pam, sure, and God knew how sorry he was for her death, but it could have been Jane.


Jane was semi-awake, hearing Dean's 'home, crappy home' as he stumbled into the motel room, obviously having issues with his gallant gesture of carrying her inside. "Put m'down." She mumbled, trying to will her eyes open.

"Sam, get the lights." Dean ordered, easing her to the floor with a bit more eagerness then he would admit. She had looked so peaceful, dried tears having left their tracks on her pale face, but he couldn't see the grief that had been in her eyes all day. He had felt bad, at the thought of waking her, so he had had this brilliant idea. He would carry her in, let her sleep, and then she'd wake up rested and fresh.

Except that Jane was heavier then she looked and he wasn't exactly running on full.

"Winchester and Winchester."

"And I'm up." Jane stopped trying to lean into Dean and popped her eyes open, immediately blinking at the unwanted light that assaulted them along with the less wanted sound of Uriel. It was probably blasphemy to despise an angel, but boy did Uriel rank really low on her 'creatures I like' list.

"Oh come on." Dean sounded less than enthused as he took in Uriel and Castiel.

"You are needed."

"Needed? I just got back from being needed."

Jane moved until she could lean back against the wall, folding her arms over her chest as she listened to the exchange. Her mind wasn't pleased at being woken up but it was processing the information, even if she wasn't understanding it immediately. She did perk up and try to tune in more when she heard mention of Alastair. She knew that name. Dean had mentioned Alastair, well, more than mention, when he had reluctantly given her some details on his time in the pit.

"…you guys are out of your league."

She was focusing on the conversation again, properly.

"That's why we came to his student." Uriel stared pointedly at Dean. "You happen to be the most qualified interrogator we've got."

Her stomach twisted into knots and began bouncing around off her ribs.


"CASTIEL!"

Sam covered his ears at Jane's screams. They had been trying to locate Dean ever since Uriel and Cas vanished with him, leaving them alone in the motel room. No success, which was not surprising. "Jane, take it down a decibel!"

She glared at him, calling for the angel again.

"What makes you think he's going to answer for you?"

"That stupid, junkless dick feels free to pop in on me whether when I'm awake or asleep whenever he see fits, the least he can do is COME WHEN I CALL!"

"Jane Winchester."

Sam nearly swallowed his tongue when Jane whirled and lunged at Cas, reaching out quickly to catch her and pulled her back against him, keeping his arms wrapped around her to trap hers. His eyes were wide as he stared at Castiel. "What's going on, Cas?"

"We have need of Dean. He will not be harmed." Castiel answered Sam but was staring at Jane, who was turning red in the face. "He will be returned once he has completed… the assignment we have given him."

"Assignment?" Jane was so ticked off she hadn't bothered doing her customary correction of his new habit of referring to her as Winchester, even though she had never bothered with changing her last name. "You want him to torture someone Castiel!"

"Alastair is not a someone, Jane, he is a demon."

"Are you really trying to justify it?"

"Dean is doing work for Heaven, it is righteous work."

"Bullshit, that's bullshit, Castiel, and you know it. You know exactly what you're asking of him, what it could do to him, and you're trying to make it all better with bullshit."


"Ugh… I can still smell them, Sam. Why, hello Jane, you're looking righteously pissed."

"Sam, seriously? Her?" Even if Jane wanted to pretend to be happy to see Ruby, it just wasn't happening.

"She can help." Sam turned his back on his sister-in-law, wondering if that was a smart idea because she had plenty of stuff to throw at him within her reach.

"I don't want to tangle with angels again, Sam." Ruby didn't sound overly thrilled at the prospect and stared up at him.

"I need you to find out where they took Dean."

"Why? They have Alastair. Dean gets himself a piece of payback. Angels get what they want. This is all a win, win, win."

"No, it's not, he can't do it."

"You don't want him to go dark side again."

Maybe Jane could pretend to be happy Ruby was here.

"He can't do it, Ruby. He came back changed, different. He's not strong enough." Sam inhaled, sparing a glance at Jane before looking back to Ruby.

"You are?" She folded her arms over her chest, looking skeptical.

"I will be."


Jane felt annoyed. She had purposefully left the motel room to avoid hearing or seeing anything she didn't need or want to see. If she hadn't seen or heard it, then she couldn't be guilty if, or more likely, when, Dean found out about Ruby's visit. Of course, if Sam didn't immediately come clean, she would have to become a snitch and spill because there would be no repeating the incident when she had purposefully not told her husband about his brother and Ruby.

Annoyance faded when they burst through the door that presumably led to Dean's impromptu torture chamber. She ignored the fact that Alastair and Castiel were fighting –wasn't Alastair supposed to be… like, chained down or something?- and rushed to Dean. Dean was lying on the floor, and the scene reminded her a lot of right before he died, with the hellhounds. The reminder grew worse when she kneeled down beside him, pulling him against her as best she could and still trying not to cause him anymore harm.

"Dean… please…" She whispered, using her fingers to brush blood away from his swollen eyes. "Not again, I can't lose you again." How many times was this going to play out? Jane looked up, searching for Castiel. He could fix this, he could fix Dean.

"Send me back, if you can."

Sam was apparently kicking Alastair's ass, and Jane got the impression Sam had juiced up before coming here. That was disgusting, and probably wrong, but right now, given what Alastair had done to Dean, she wasn't splitting hairs.

"I can kill now." Sam said, right before holding out his hand.

She turned her face down as Alastair began screaming.


"Jane…"

Jane didn't look up when she heard Castiel. She simply remained where she was, standing next to Dean's bed, holding his hand and staring down at him. He was still unconscious, hooked to an IV, covered in bandages, and was breathing only thanks to the tube they had stuffed in him. "Fix him." She ordered in a low, rasping voice.

"Jane…" He stepped back, out into the hallway.

Frowning, she reluctantly followed him. "Get in there, and heal him, now, Castiel. You owe him that." She impressed herself with how calm and steady her tone of voice was.

"I can't."

He was threatening to derail that calmness and Jane struggled not to make an attempt at slapping an angel of the Lord in the hospital hallway. "You did this to him! You and Uriel put him in there! You promised me he wouldn't be harmed, Castiel."

"No."

"Castiel! He didn't want to do this and you made him and now you're going to leave him there to die?" Angrily, she reached up and wiped away the tears that were beginning to fall. "He deserves better than this." Her voice was now a harsh whisper, both breaking and quavering as she fought to keep it together. "He did what you wanted, and you blew it. You blew it because you stupid angels couldn't manage a damn Devil's trap."

"Castiel!"

Jane didn't stop staring down the angel as Sam walked up, two coffees in hand.

"Are you going to heal-"

"No." Jane interrupted, flatly. "He won't. He won't help, Sam. He can't."