Warnings: Non-explicit torture of a non-main character by a main character. Sort of canon.

A/N: I swear this is a fix-it. Things will get happier in the next two chapters. Also, I start diverging from the Supernatural canon here so if things don't line up with episodes or actual plot that's why.

Dean: Call when you have time?

Clint: Yeah, after my debriefing

Dean: I want to debrief you

Clint: You suck

Dean: And swallow ;)

Dean stares at the picture in Bobby's book as he waits for Clint to call and Sam to get back with pie. He's not sure which one he wants more right now.

His phone buzzes, catching him off guard, and Bobby rolls his eyes before heading into the kitchen.

Dean flips open his phone. "Was it boring?"

"For once, no. Explaining to people that Norse gods exist is kind of fun. What did you want to talk about?"

"We summoned Castiel last night," Dean says. "The thing that raised me." That gripped me tight and raised me from perdition. Dean rolls his eyes. Who even talks like that? He can hear Castiel's voice answer in his head, an angel of the Lord. Dean really doesn't want to believe that, but the picture in Bobby's book is pretty good proof.

"Thing?" Clint asks. "You still don't know what he is?"

"He claims to be an angel."

I'm an angel of the Lord.

Clint whistles. "An angel? I guess if demons are real then angels would be too, but damn. An angel rescued you?"

"I don't believe he's an angel. Well, maybe I do. Damn it. Before last night, I didn't believe in angels."

Clint's voice is quiet as it comes through the phone. "Apparently they believe in you."

What's the matter? You don't think you deserve to be saved? Because God commanded it. Because we have work for you.

"They didn't do it out of the kindness of their hearts. If they even have hearts. Apparently they have work for me. They—" Dean pauses when Bobby stumbles into the room, all the color drained from his face. "I'll call you back. I think I just got a job."

"I would tell you to be safe, but apparently you've got angels watching out for you."

Any other time Dean would argue with him, but he needs to find out what's wrong with Bobby so he just hangs up.

"What's happened?"

"Something's wrong with Olivia. We need to get Sam and check on her."

Dean: I hate angels. Dicks with wings. No, not even that because they don't even have dicks. Junkless douche bags

Clint: Do we need to talk?

Dean: I hate Sam. I hate Ruby. I hate Lilith.

Clint: Dean?

Dean: I hate everything

Dean's phone buzzes, a call instead of text, and he waits for it to ring three times before flipping it open.

"I don't want to talk about it," Dean says.

"Then why did you pick up?"

Dean's quiet for a moment, considering. "I hate you too."

Clint laughs. "You don't mean that. Tell me what happened."

"Castiel sent me back in time to watch my grandparents get murdered, my dad die, and my mom make a deal with a demon to bring him back. And in case that wasn't shitty enough, turns out Sam's been infected with demon blood since he was a baby, and if I don't get him to stop screwing around then the angels are going to kill them. So, I hate everything."

"They are dicks."

"I know!"

"But you don't hate everything."

Dean sighs. "I don't hate you."

"Want to get a drink?"

"I thought you'd never ask. I have a couple beers in the fridge. You want to see if we can find a hockey game to watch while we drink?"

"We'll pick teams," Clint says. "Every time my team gets a hit, you drink. Every time your team gets a hit, I drink. Goal means you finish your drink."

"Turning hockey into a drinking game?" Dean asks. "Are you trying to get me drunk, Agent Barton?"

"I found a Penguins-Flyers game. I pick the Penguins."

Dean flips to the right channel and grins as he leans back into his arm chair. "Definitely trying to get me drunk. These two teams get physical. Too bad I'm in Kansas and you're wherever the hell you are. I'd like to get physical with you."

Clint groans. "You have the worst pick-up lines."

Dean grins into the receiver. "That's what years of porn will do to you. Aw, damn it, Crosby." He takes a long drink. This is going to be a long game.

Dean: I didn't know it was possible to hate angels even more

Clint: What now?

Dean: They want to wipe out a whole town. They do realize they're supposed to be protecting humans, not killing them, right?

Dean leans back against the park bench and watches the children scrambling over the playground. There's a group of giggling ones that are playing don't-touch-the-ground tag, and they shriek as they dodge the boy with the striped shirt who's it. There are two girls showing off on the monkey bars and over toward the end of the playground an older brother is helping his little brother with the zip line.

Dean feels a weight lift off his chest as they play. He knows he should be upset because another seal was broken and that brings them closer to the apocalypse, but that's the future, and the future has always been hazy and uncertain in his mind. What he knows right now is that all these kids are playing, carefree and happy, and it's because he didn't let a bunch of angels burn the town to the ground.

He doesn't understand why Cas can't comprehend Dean's lack of faith. He'd always been taught that angels were pure goodness, that they were supposed to protect, and then he'd been taught that angels didn't exist, and now that they're real they're nothing like he thought they'd be. They're calculating and have a casual approach to human life that he can't accept.

Dean's thoughts are interrupted when Cas appears beside him, and he really needs to put a bell on the guy. At least he hasn't appeared in Dean's lap yet; though, that's only a matter of time. The guy has no sense of personal space.

"These people," Cas says looking around them, not only at the kids but also at their parents and babysitters, "they're all my father's creations. They're works of art."

Dean looks at Cas, really looks at him for a moment, and wonders if he's telling the truth. Uriel had been ready to destroy the town without a second thought, ends justify the means and all that, but if Castiel agrees with Dean then maybe Dean has an ally in heaven. Maybe not all the angels are a bunch of lousy bastards.

"I have questions," Cas admits and he looks Dean in the eye as he says it, even though this is an intensely personal confession. "I have doubts. I don't know what is right and what is wrong anymore."

There's something so open about Cas's face that Dean wants to look away, because it's almost too painful to bear. Cas who is the embodiment of faith, who trusts without knowing, who believes without reason, is starting to be unsure, and this is what Dean had wanted, for Cas to stop being such a freaking soldier, but now that he can see Cas breaking in front of him, he wants it to stop. He wants Cas to believe again, to wipe the crushed look of despair on his face.

Dean knows what it's like to be disappointed in someone you trust. He knows what it's like to realize that that person you've always looked up to isn't all they're supposed to be, and he knows how that cuts at you, because you've listened to them all this time, and if they're wrong, then maybe you've been doing wrong when you thought you were doing good. He knows that he's nothing like Castiel and John Winchester is certainly no God, but he understands the kind of pain Cas is going through.

He wishes he knew how to make things right.

"Ruby's helping me," Sam says. "She saved my life!"

"She's making you drink demon blood," Dean argues. He couldn't believe it when Cas had told him. At first he'd been pissed because Cas had showed up and said 'I was spying on your brother' and then he told Dean what he'd found out, and Dean stopped being pissed at Cas and started thinking of ways to strangle Sam. How does Sam not see what's wrong with this? "She's twisting you, and maybe you needed her while I was gone, but I'm back now. I can protect you."

"I don't need you to protect me. I can protect myself now."

"Right," Dean says. "As long as you're hopped up on the demon 'roids."

"You have no right to judge me," Sam says. "You left me on my own, because you were too weak to face the world without me. I'm sorry that you don't like how I coped, but it wasn't exactly easy for me having to live without you."

Sam grabs his jacket off the bed where he'd tossed it when he came in.

"Where are you going?" Dean asks. Is Sam seriously walking out on him? Sam who always demands that they talk out their issues? He's going to leave when Dean's trying to have an actual conversation with him?

"Out," Sam answers. He doesn't say anything else, just stomps out of the motel room, making sure to slam the door behind him.

"Damn it." Dean punches the wall. "Damn it! Damn it! Damn it!"

"Does that actually make you feel better?"

Dean spins around, fist raised to see Cas standing right behind him. "Would you stop doing that!"

Cas tilts his head to the side. "Doing what? Coming to you when you are distressed?"

Dean takes a deep breath and reminds himself that punching angels is not a good idea. Most angels he'd punch without a second thought, but Cas had pulled him out of hell and was at least trying to be less of a dick these days.

"Never mind," Dean says because he doesn't want to chase Cas away. Not right now when he needs someone to keep him from chasing after Sam and strangling him. "I'm worried about Sam."

"There are many who worry about him," Cas says. "He is headed down a dangerous path, and there are many who will stop him if he does not stop himself."

Dean knows exactly what Cas means by stop him, and he doesn't want his brother to be killed by angels. "What can I do? He won't listen to me. Ruby's gotten to him, I just don't know why."

"Ruby knows."

Dean rolls his eyes. "Thank you, Captain Obvious."

Cas's forehead crinkles into a frown. "I'm not a captain."

"It was a reference that obviously you wouldn't get, because you never get any of my references."

"Ah," Cas says but he doesn't look any more enlightened. "What I was trying to tell you is that if you want to know Ruby's intentions for Sam then you should ask Ruby."

"What and she'd just tell me hell's nefarious plans for my brother?" Dean flops down on his bed. "I can see that conversation going over well."

"Dean," Cas hesitates and that gets Dean's attention, because Cas is never delicate about anything. He's even more worried when Cas looks past him at the wall instead of meeting his eyes. "If you were determined, you could coax the answers from her."

Dean's blood runs cold for a moment. Cas isn't suggesting, he couldn't possibly be, but he is. Dean closes his eyes, and all he can see is Alastair. The sharp curve of his smirk, his smug victory as Dean accepted the knife, as Dean walked up to his first victim.

"I'm not sure I can do that," Dean says. "I'm not sure I'd come out of it in one piece." Not that he's exactly put together right now anyway. He'd come out of hell broken, wounds that refused to heal, memories that refused to be buried, and he has no one that can help him. He doesn't know how to turn to Sam or Clint and broach the subject of hell and torture and how Dean had put himself over other people, how he had learned to torture and been damn good at it. Taught by hell's best.

"You are the strongest person I know," Cas says.

Dean laughs, short and deprecating. "I feel bad for you then, because I'm pathetic. It only took thirty years to break me. I'm supposed to protect people Cas, and I broke them instead."

"You did what you had to to survive."

The worst part about having an argument with Cas, Dean reflects as he imagines all the ways he'd like to kill the angel, is that he always means everything he says. He doesn't lie, and he doesn't say anything that he doesn't believes with all of his being, and that makes it really hard to be angry with him. Or to successfully sway his opinion.

"I should've been stronger."

"Perhaps you needed to learn a skill for a later time in your life."

Dean opens his eyes to glare, because that sounds way too close to 'everything happens for a reason' and he doesn't want excuses, and he doesn't want a lecture on fate or other things outside his control. As much as he'd like to shove his guilt off on a higher power or an ineffable plan, he can't. He has to take ownership of it.

"I have upset you," Cas says, a statement more than a question. "I apologize."

"It's not your fault," Dean says. "I'm the one who couldn't hold out long enough."

Cas hesitantly sits down on the far corner of Dean's bed. "I regret that I did not reach you sooner. No one should have to suffer as you have."

Dean sighs and pulls a pillow over his face. "Can we talk about something besides my time in hell?"

Cas is silent for a long moment. "Did you know that I am the angel of Thursday?"

Dean sits up. "Really? Thursday?"

Sam comes back, his eyes shining and a hard set to his jaw. Dean knows immediately where he's been.

"I don't want to talk about it," Sam snaps before Dean can even open his mouth.

Dean holds up his hands. "Wasn't going to say anything, but you're obviously in a shitty mood. I'm going to take a walk."

Sam frowns. "You don't take walks."

And you used to be a good kid, Dean thinks but doesn't say. Instead he shrugs and heads out the door. He shoves his hands into the pockets of his jeans and his fingers brush against his cell phone.

He pulls it out as he heads down the darkened road.

Dean: What's SHIELD's policy on torture?

Clint: We do what's necessary. Why?

Dean: Have you ever?

Clint: I'm the guy they call in for the kill, not for the questions. Everything okay?

Dean: Fine. Sam and I are debating ethics of war

Clint: You're ridiculous. And it's late. You should be sleeping

Dean ignores the last text and kicks a few loose stones as he travels further and further away from the motel. There's nothing down this part of the highway except for trees and a guardrail. The more he walks, the more he loses the lighting of the motel sign, the more he gets swallowed up by the darkness.

We do what's necessary.

Dean breaks into a jog, and he goes until he's lungs are burning, and he can barely see the flicker of the neon lights. There's a curve just ahead, and if he keeps going he'll lose the motel completely.

He stops where he is and turns his face up the sky. "Cas, I need your help."

He feels stupid talking to the sky, but he doesn't know what else to do.

"I am here," Cas says and he lays a hand on Dean's shoulder. "I will always be here when you call. What do you need?"

Dean turns to face Cas, and as he pushes Cas's hand off his shoulder, he finds his fingers lacing with Cas's, and he squeezes, a desperate need for something he can't name.

"We need to catch ourselves a demon."

Cas nods solemnly. "I will assist you. And Dean?" His free hand cups Dean's cheek, his thumb brushing away the tear leaking from Dean's eye. "I am sorry it has come to this."

"Me too," Dean says.

Getting Ruby is easier than Dean had expected; though, he knows better than to think that anything will be easy from here on out. She's hanging from the ceiling of a warehouse in rope that's been soaked in saltwater. Her ankles are tied as well and latched to rings on the ground to keep her body still so Dean can work.

There's a devil's trap on the ceiling and floor, and Cas is standing just inside the door in case there are any problems. Dean doesn't want him here watching this, but he doesn't want to risk Ruby getting free.

Sam is working with Bobby on a case involving a shower-spirit. Dean had called Bobby and asked him to take Sam on a case, because Dean had some work to do. Neither of them know what he's up to, and he feels guilty for deceiving them, but not as guilty as he does for what he's about to do.

He really hopes that he's right, and Ruby has some good information or he might break into too many pieces to be fitted back together again. And that's only if Sam doesn't kill him first.

Dean looks over the dark haired woman he has held hostage and wonders what Sam sees in her. What can she offer him that's made him into someone Dean can barely recognize? No, these thoughts are useless. He needs to be calm, rational, emotionally detached if he's going to do this right. Alastair had taught him that emotions were weakness. He needs to be calculating, to evaluate what measures will produce the best results.

Dean picks up Ruby's knife and holds it up so she can see. "I'm not sure if I ever thanked you for giving this to us," Dean says as he approaches. Slow, even steps that she can count, anticipate. "So thank you."

He stabs the knife between the veins in her wrist. She clamps down on her bottom lip to keep from screaming, and Dean twists the knife.

"I hope you don't try the stoic act for long," Dean says leaving the knife sticking out of her flesh as he goes back to his table. "I have questions I want answered, and I'm on a bit of a schedule. Though, maybe I'll keep you all strung up until Sam gets back, and see who's side he's ultimately on."

Ruby's eyes flicker with hellfire as she glares at him. "That's what this is? You're throwing a tantrum, because your brother likes me better?"

Dean's lips pull back into a poor imitation of a smile. He picks up a bag of salt and heads back over to her. "No, I want answers. What are your plans with my brother?"

Ruby laughs. "You honestly expect that I'm going to tell you?"

"Oh, darling," Dean says, pulling the knife out, "You're going to tell me everything."

He sprinkles salt over the fresh wound, and she bites through her lip with the effort it takes not to scream.

In the end, Ruby probably doesn't tell Dean everything, but she tells him more than he thought she would. He hadn't realized the extent of hell's machinations before, but he certainly does now, and it takes all the self-control he has not to stab the bitch through the heart with her own knife.

Ruby's training Sam to take on Lilith, but also so that Sam can break the last seal and thus break Lucifer free of his cage. Apparently Sam is destined to be Lucifer's vessel, the human he uses to bring on the apocalypse. There's no way Dean's going to let that happen.

He and Sam are going to kill Lilith before she becomes the last seal, and they're definitely not going to kill her near any convents. And now, thanks to Ruby, he knows where Lilith is going to be shacking up for the next week.

Dean's washing his hands in the sink when his pocket buzzes. He quickly dries his hands and pulls his phone out.

"Where the hell are you?" Sam demands. "Bobby and I are at the motel but all your stuff is gone."

"Cas is coming to get you," Dean says and Cas nods before disappearing. "Did your hunt go well?"

"Yeah, we," Sam's voice cuts out but then Sam and Bobby are standing in front of Dean. "It did." Sam frowns and looks around the dingy room. "Where are we? What's going on?"

Dean's eyes flick toward the door that separates them from Ruby. "I've been talking with Ruby."

Sam raises his eyebrows. "Talking?"

Dean shrugs. "Some other stuff mixed in. I managed to catch her in a chatty mood. She's not your friend, Sam."

Sam's shoulders shake with the effort it takes him not to walk away, or punch Dean in the face. "She told you that?"

Dean's smile is full of sharp white teeth, and he notices Bobby take a step back. "The only thing she hasn't lied about is that she wants you to kill Lilith."

"Well, I want to kill Lilith so we're a good match." Sam crosses his arms over his chest, preparing for a fight.

"We will kill her," Dean says, "but we're not following Ruby's plan. Ruby's plan ends with Lucifer rising from hell and possessing you." Sam's mouth falls open and Dean presses his advantage. "We're hunting Lilith as soon as you're ready, Sam. We're finding her, and we're killing her, and we're not going to trigger the apocalypse in the process."

Sam's mouth opens and closes for a few moments as he processes. "What? How? Ruby said the only way to kill Lilith is for me to get stronger."

"So you will." Dean ignores the surprise on Sam's face. "I have a demon full of blood waiting for you to drink. Will you need more than one?"

Dean's aware of Bobby reaching toward his back pocket where he keeps a vial of holy water, just in case, and he's aware of Cas standing silently to the side, watching the proceedings without judgment or pity. He's also aware of Sam struggling to figure out what's happened to his brother.

"I thought you were against the demon blood."

"I am," Dean says walking toward the door, "but sometimes we do what's necessary to win."

He throws the door open, and Sam takes a cautious step forward. Dean knows the moment he sees Ruby, hanging in the ropes, her body cut and bruised and even burned in some places. Sam's head snaps to the side, mouth falling open.

"Will you need more than one demon?" Dean repeats.

Sam slowly shakes his head.

"Good, I want to get on the road as soon as possible. Use her knife to slit her throat or her wrist or wherever you prefer to feed from but don't press too deep. It wouldn't do for you to kill the demon before you can drink its blood. If you don't mind, I'm not going to watch the actual blood drinking."

Dean walks back to the front door of the factory, not waiting to see if Sam's going to move. He knows Sam will. Dean leans his head against the single window on the door and hopes that this works. He and Cas had talked after they wrung all the useful information they could out of Ruby. There are plans for a battle to take place between heaven and hell with Earth as the battlefield and humans as the casualties. Dean has no desire for that to take place, and he's going to do everything in his power to stop it from happening.

"Son," Bobby says, his hand heavy on Dean's shoulder.

Dean shrugs off Bobby's hand. "I don't deserve that."

"No," Bobby agrees. "You probably don't. What you did back there," Bobby shudders and he's so close that Dean can feel it, "that's dark, Dean."

"I know."

"Why?"

Dean presses his forehead harder against the cool pane of glass and looks out at the sun that's beginning to poke its way above the trees. He'd lost track of time locked in the windowless room with Ruby. He'd forgotten that the night was passing and that day would come again. He wants to push the door open and feel the sun on his skin, but he doesn't move.

"She's a demon, Bobby. She wanted nothing good with Sam, and I got tired of the cryptic hints people keep dropping and the doubt and the not knowing, and I wanted to find out what she wanted before she broke him so completely that I wouldn't be able to put him back together."

"And you?" Bobby asks. "Can you be put back together?"

The sun hits the glass, but Dean can't feel it, the glass is too thick. He turns away from the window and toward Bobby who is watching him with concern from under his baseball cap. "I came back broken. This," he motions towards the room with Ruby. "This isn't anything new for me."

Bobby's eyes fill with understanding then pity, and Dean has to walk away.