Warnings: Discussion of murder, suicide, and addiction. If you need specifics before you feel comfortable reading, send me a PM. I will reply as promptly as I can.

Shout outs to podothedruid, Eyum daRelmera, NeteleJala, superchiwo, Damaged Emerald, and gnbrules for taking the time to leave reviews, and thank you to everyone who has favorited, followed, or even just read this story. I hope you're all safe and healthy, and that Sam's backstory lives up to the hype. =)

Chapter Sixteen

Castiel had thought that Dean was a big man. Sam Winchester was bigger. Even sitting down he looked tall, and the cafe's signature oversized coffee mugs looked like part of a child's tea set in his huge hands. But while Dean took on the world with a grin and a wink, projecting confidence no matter what he was feeling on the inside, Sam held himself cautiously, arms pulled in close, shoulders a little hunched, trying to make himself small. Castiel wondered if that was a defense mechanism he'd learned in prison or if he'd always been that way.

They'd been sitting in awkward silence for almost a full minute. They both knew what they were here to talk about, but neither of them seemed to know how to start.

Finally Sam said, "Cas, I …Do you mind if I call you Cas? Sorry. Dean told me what it was short for, but I can't remember."

"It's Castiel, and I think I'd prefer that, at least for now."

"Of course." Sam ducked his head contritely. "Castiel. I want you to know that I really appreciate you giving me this chance to earn your trust."

Castiel looked at him steadily, trying to decide if he was sucking up, but there was only sincerity there. Castiel rewarded it with a truth of his own. "You're an important part of Dean's life, and Dean is an important part of mine. Whether we can all be part of each other's lives remains to be seen, but I owe it to him to at least try. I want to be perfectly clear on one thing though. Even if I decide to trust you, that trust can still be broken. If I ever feel you're a danger to my daughter in any way, it's over. There will be no second chances." He didn't insult Sam's intelligence by asking if he understood.

Sam nodded, and he didn't shrink under the weight of Castiel's gaze. He actually seemed to gain a little confidence, sitting up straighter. Castiel wondered how long it had been since someone besides Dean had spoken to him like an equal. "He loves you, you know," Sam said out of the blue.

Castiel felt a faint smile steal over his face. "I know," he said quietly.

"Yeah, but … I don't just mean he's in love with you. That too. You don't even need to know Dean very well to see that, but …"

Sam chewed his lip and looked out the window at the busy Midtown street, searching for the right words to explain himself. Castiel waited.

"The other day, when you called him and you were upset, and he dropped everything to be there for you? That's what he would have done for me. That's what he does for family. I've never seen him act that way with anyone he's dated, and that's why …" He looked at Castiel again. "That's why I'm going to tell you the whole story. I don't like talking about it, so this is a one time deal, but if Dean says you're family, then you deserve the whole truth, so here goes."

There was another silence while Sam got his thoughts in order, but it wasn't nearly as awkward. Somehow things had shifted. Castiel was no longer sitting in judgment on Sam. They were working together to bridge the gulf between them and make this strange little patchwork family work.

"When I was in college," Sam started, "I met this girl. Jessica. She was …" His face got a look halfway between joy and pain. "She was perfect. Gorgeous, kind, smart, and for some bizarre reason, into me. I fell so hard and fast, and I never looked back."

Castiel could already tell that this story did not end with 'happily ever after'.

"When we were twenty one, I scraped together the money to buy a ring. I only told two people — Dean, and my best friend Brady." Sam closed his eyes and took a deep breath, steeling himself for the bad part. "Well, it turned out Brady had a drug problem, and he was in debt to some pretty dangerous people. He thought that diamond would get them off his back, so he went to our apartment when I wasn't home, and of course Jess let him in. Why shouldn't she? He was our best friend. I don't know exactly what happened next, but it ended with Jess bleeding to death on the floor. I found her hours later."

Castiel tried to imagine what that must have felt like. His brain supplied an image of Dean lying in a pool of blood, and he quickly shut down that line of thought. "So you killed Brady?"

Sam shook his head. "No. Not saying I wouldn't have, but Brady beat me to it. He overdosed on purpose, left a note confessing to Jess's murder. As far as the police were concerned that was the end of it. Except it wasn't. Not for me. And I'm not saying what happened to Jess justifies what I did next. She would have been ashamed of the person I turned into. I'm not trying to justify anything. I'm just giving you the whole picture."

Castiel nodded. "I understand. Go on."

Sam took a moment to collect himself again and continued. "It started with alcohol, but it didn't take me long to graduate to other things. I lost my law school scholarship, had to drop out. That probably should have been my wake up call, but I kept going. No school just meant more time to get high. And I know what you're thinking. Where was Dean in all this? Right?"

Castiel didn't deny it.

"He didn't know. I mean, he knew about Jess, but after the funeral I basically dropped off the face of the Earth. I stopped answering his calls. I moved without giving him my new address. He called the university office and found out that I'd quit school. At that point he didn't even know if I was alive. I put him through hell, but at the time I told myself I was protecting him. If he knew how bad things were, he'd sacrifice everything to help me. He'd spend all the money he'd saved for his restaurant on rehab for me. That's just who he is. He takes care of the people he loves. I told myself that this way at least one of us would get to live his dream, but the truth was I didn't want to be saved. I just hadn't worked up the nerve to do what Brady did, so in the meantime I was doing every stupid, reckless, self destructive thing I could think of.

"Then I met another girl. Ruby. She was the complete opposite of Jess, and calling it a romantic relationship would be way too generous. She was a dealer, and she liked me enough to let me pay with sex instead of money. I was running out of money by then. After a while she started using me for other things too. I would, um … encourage people to pay their debts. I didn't enjoy it. I had to get high to do it, and even then it made me sick, but it was that or Ruby would cut me off, and I was an addict. Getting cut off from my supply was the worst thing I could imagine.

"One night, me and Ruby were out working the clubs. I was high as a kite, but Ruby had me driving so she could count the money. She never let me handle the money. And … Well, I don't remember it clearly. I remember a bright light and feeling the car spin out of control, and then I woke up handcuffed to a hospital bed. They told me Ruby was dead, and since I was driving while intoxicated, I was being charged with second degree murder. I did the only thing I could think of. I called Dean. And he did exactly what I always knew he would. He spent almost every penny of his savings to get me a good lawyer and pay for my treatment. If you ask him, he'll say he doesn't regret it, and he'll mean it. But I regret it. My stupidity cost him his dreams, and I can never pay that back any more than I can bring Ruby back to life. I regret that too. She wasn't a good person, but she didn't deserve to die."

When Sam finished his story, Castiel could only sit in stunned silence for several long minutes. The cheerfully normal noise of the cafe continued around them, but it couldn't touch their little bubble. Sam waited patiently while Castiel processed everything he'd just heard.

Honestly, Castiel thought, the worst part was how horribly familiar it was. If his life had taken a slightly different turn, if Cain hadn't showed him how all that anger and helplessness could be channeled into food, he would probably have landed himself in prison sooner or later. And he wouldn't have had a brother like Dean.

But just because he could relate, that didn't mean he was ready to completely trust Sam. "I presume you're clean now," was the first thing he said.

"Eight years. And one of the conditions of my parole is that I attend weekly NA meetings and submit to random drug tests. No driver's license either for at least two more years. Not sure I'll want one even when I can. Haven't been behind the wheel since … I have no idea what it would do to my head."

"And you have a sponsor? Someone besides Dean you can talk to if you feel like you're in danger of slipping?"

"Yeah. He's an ex-con too, so he gets the whole situation, not just the addict part."

Castiel nodded. When he took a sip of coffee to buy some time to think, it was stone cold. He grimaced and pushed away the mostly full cup. "How about you join us for dinner tomorrow, Sam? We usually eat early because Dean and I have to be at the restaurant before the dinner rush. Does four o'clock work for you?"

Sam lit up. "Yeah. Sounds great."

~o0o~

When Castiel got home, Dean and Claire were playing Monopoly, and it looked like Claire was winning. Dean looked up from the game, hope and fear warring on his face.

"Sam is coming to dinner tomorrow," Castiel said, not wanting Dean to suffer a moment longer than necessary. "You are of course invited too."

Dean was on his feet in an instant and pulling Castiel into a bruising hug.

Castiel laughed and hugged him back just as tightly. "What kind of food does he like?" he asked when Dean let him breathe again.

"Vegetables," Dean said promptly. "He's always been a health nut. Although lately he'll eat anything that's not prison food."

From her place on the floor, Claire tugged on Dean's pant leg, then pointed insistently at the game board.

"Yeah, yeah," Dean said. "I'm coming." He sat back down, and Castiel sat beside him, leaning against his shoulder as though it was the most natural thing in the world.

"Well, it looks like this game is almost over," Castiel said, observing the pile of properties in front of Claire and the dwindling supply of cash on Dean's side of the board.

"Kid's a budding loan shark," Dean grumbled fondly, reaching over to ruffle Claire's hair.

Claire giggled and rolled the dice.