Turns out he hadn't dedicated a whole playlist to turning this trip into a musical torture chamber for me. The next songs that came on were a mix of good old standbys and new stuff that he'd figured I'd like.

"So why'd you wait til we hit the freeway before you played that crap song?"

He shrugged, "Figured you wouldn't tuck and roll if we were doing eighty."

He knows me way too well, "Oliver and Roy are bad influences on you, you're thinking you're way through things like this way too much now."

"Actually, that was more Dig's influence then either of them. He and I spend a lot of time talking strategy on hunts when I'm over there. He is former military after all."

"Oh yeah, I forgot." That made a lot of sense actually.

"So's Lyla actually, that's how her and Dig met, they were in the same unit back in the day."

"Really? I didn't know that." Which explained why Lyla had always seemed pretty solid. I knew she did some sort of top secret, black ops stuff for the government but never asked for details.

"They have some interesting stories."

"I bet." My brain was churning through all of that, adding that in with the things Roy had said a year ago when he wanted to hunt with Sam and I, then decided to keep hunting. "Huh, out of curiosity, how much does Oliver listen to Dig on things?" I knew they were close but Oliver and I had clicked for a lot of reasons, one of them being sheer stubbornness.

"You remember how jacked up the group was back then?"

"Yeah?"

"Well, one of the times I was there Dig came home pissed as hell because Oliver was trying to pull another martyr act and he went into the whole backstory of their history from his view and how he'd gotten fed up with trying to get Oliver to understand things. Early on Oliver had paid a bit more attention to Dig's advice, then for some reason started ignoring him until things had gotten so out of hand the situation was almost beyond saving. I knew exactly how he felt and told him to just lay it all out. So he tried, from what Roy said he got in on a few of those talks as well, they didn't go easy on Oliver either. He explained to Oliver why he was splitting his time between Oliver and hunting with me, how the drama was driving wedges into the group and Oliver needed to make some serious choices. Roy was about two steps from just hunting full time with me, he honestly thought that was safer for him then working with Oliver."

"Really? Wow, it was that bad huh?"

"Guess so, Oliver kept being stubborn though, then Felicity piled on and said she'd leave Oliver high and dry if he kept being an idiot."

"Damn, that had to hurt." I knew how much Oliver loved her, even though it'd taken him a long time to admit it. I had no room to judge him on that, that's for sure.

"Yeah, well he almost made the wrong choice. I was there when Felicity showed up at Dig's in tears because Oliver still didn't get it. So I took steps."

"Uh oh," Sam had deeper ties with Oliver's group than I did and I knew he cared a lot for Felicity, he saw her as the reason he'd pulled out of the depression my going to Hell had left him in. "What'd you do?"

His jaw tightened, apparently it still bothered him that Oliver had hurt her. "I tracked his ass down and told him point blank that if he was too damn scared to love her how she should be loved I'd be more than happy to provide a comforting shoulder for her to cry on."

"You what?" That was pushing some serious boundaries. Even I'd never made moves on a girl that was already hooked up, at least as soon as I knew she was with someone. "That's a bit low don't you think?"

"Maybe, but it got his attention. After he took a few swings at me he settled down enough to finally think. I told him he was going to lose everything he'd worked for if he didn't drop the walls, drop the self-loathing and finally get off of that damn island and over the years of hell he'd been through. I told him he was better than this, everyone else saw it but him."

"Sounds familiar," I muttered.

"It should. After that he called all of them together and finally listened to what they had to say. So in a round about answer to your question, he actually listens to Dig a lot, now that he's actually paying attention again."

"Sam, would you have? The thing with Felicity?"

He sighed, "Another place, another time. If she wasn't in love with him, I'd sure as hell try."

"He knows doesn't he?"

"They both do, I didn't say anything, didn't have to, but it's not an issue. He knows I wouldn't ever try anything and I respect her too much to put her in that situation."

That explained a few things, "That's why you're still hunting?"

"One of the reasons, not the main one though. I'm still doing this because I want to and because all that knowledge in the Bunker, it needs to be used, saved, passed down. The things we could have prevented, the lives we could have saved if we'd known then what we knew now. Between what Felicity and I have come up with as far as toys and what we've learned from the books, less and less hunters are dying Dean. Less of us are ending up hurt or possessed. I've been tracking things like that. I made a list once, I asked around and found out how many hunters got killed the year before you retired and I started delving more into things. This last year? We've almost halved that. More hunters means more lives that are getting saved, less monsters." There was a sense of actual accomplishment behind his words, I remembered feeling that once, decades ago, "I can see that what I do is making a difference, finally. After all these years. It's not just about surviving a hunt and going to the next anymore. It's much more than that for me now."

When we first started hunting together as adults, I'd had a few years of hunting on my own under my belt, thought I knew it all. Looking back I started to wonder what our lives would have been like if I had listened to him more and less to the memory of Dad. There was a damn good reason he'd gotten into college and kicked ass on those tests to get into law school, I was just too full of myself to see it. "Proud of you, Sam. Really am, I think Dad would be too."

"Thanks Dean, but no offense, that's not what matters to me, what Dad would think. What I care about is if I can sleep at night because I'm not hurting people anymore. Doing things this way, I can."

"None taken." He'd never lived for anyone's approval, even mine. If he had, he wouldn't have gone to school. I used to think that was a bad thing, now, not so much. "I know one person who you have probably pissed off though with all this new and improved hunting. Crowley. Even though you and Roy have been avoiding demons and I sure as hell want nothing to do with them, hearing all this I can't imagine he's been taking it in stride. He's got to be pissed." That's when I knew Sam hadn't exactly been straight with me about demons.

"Yeah, about that. I did have one more run in with him, about a month after you moved out and I saw you were sticking with your decision to quit. There's a reason Roy and I haven't tangled with any demons and you haven't got a whiff of them either. He's scared shitless of me now."

"What?"

"I found a spell to summon hellhounds.."

"Well that would have come in handy about three or four years ago," I interrupted.

"I know, right? Anyway, as we know, Crowley's got eyes everywhere. I knew it'd get back to him eventually that you weren't hunting with me anymore and he'd try to get a fix on where you were."

"Sort of the reason I have Devil's traps under every rug in the house and two in the bedroom."

"That many? Damn."

"I put them down when all that open space confused me, I wanted to be thorough." Coyote had thought I was overdoing things a bit but she didn't stop me.

He nodded, "Well that's thorough all right. Back to the hellhounds and Crowley. I set up another Devil's trap surrounded by goofa dust in the dungeon and summoned one then Crowley right after, Cas was with me too. He misses you by the way."

"Crowley?" That was disturbing.

"No you idiot, Cas." There was speculative look his face as he maneuvered through some early morning traffic. "Since you're more sure of things now maybe you can give him a call."

After the whole ridding me of the Mark thing and my choice to take a break Cas and I had a long talk. Well I talked, he peered into my soul and told me what I was really thinking then made the choice to keep his distance for awhile. I hadn't wanted to come out and tell him that I needed a break from everything dealing with Heaven, Hell and alternate realities. He knew though and he didn't take it personally. His relationship with us had always broken every rule of human/angel interaction and try as he might, Cas was and will always be a soldier of Heaven, which meant that where he was, demons and angels were bound to show up at some point or other. I'd missed him too but I knew it was for the best that he wasn't around while I tried to recover from the Mark. I still wasn't too comfortable with the idea of having him back around. "We'll see. Maybe I'll drop by the Bunker and we can hang out there. Back to you and Crowley."

"Right. So he showed up, saw the hound, saw Cas and started speechifying like usual and that's when I shot him with a Devil's trap bullet to get his attention. Then I put Ruby's knife to his throat and told him how things were going to be. The new rules were hands off you, hands off me and Roy and I don't close the gates to Hell right then and there. I had two of the three trials right there and Cas could take me to grab a soul from Hell if need be. I pointed out that you weren't there to stop me and I'd see it as a parting gift to you if I wiped every demon off the face of the earth before I died."

It was probably a good thing I wasn't driving or there would be some screeching brakes right about now, "You said what? Sam! What the.." The sheer determination on his face stopped me.

"No one, not Crowley or anyone else was going to trash your retirement."

"And you dying would have made it any better?"

"If a demon caught you off guard and took you out when I could have prevented it I would have ended up dead anyway, because you can damn well bet I'd be doing the same thing. Closing the gates and finishing what I started. I wouldn't bring you back, you've suffered enough, but I'd take out who or whatever had killed you."

"And you've been bitching about me doing the martyr bit?"

"Stuff it, I knew Crowley would back down, he's too slimy not to. Although I was really hoping he wouldn't, I've been wanting to kill him for years, he knows it too. I also tossed into the threat that once I'd cured him and was dead Cas would kill him and take him to Purgatory since Hell would be closed. Cas, for some reason, chose that exact moment to go all angel and pull out the burning blue eyes bit while standing over Crowley with an angel blade. He took one look at me, the hound and Cas, nodded and signed a very one sided contract that I'd written. It basically stated that all current and future Winchesters, Roy, Thea and Oliver's people are off limits or we send him and his kind packing. Once he signed I pulled the bullet out of his leg, broke the traps and he and his dog left. Haven't seen or heard from him since."

Admittedly I was the one with with the reputation of being a badass, most of the monsters and demons would rather deal with Sam than me. They thought he was somehow a nicer guy, they were wrong. You don't survive what he had and not be able to dish it out when the chips were down. Even though I didn't really agree with the motive behind the threat I was bummed that I missed seeing him scare the King of Hell into making a deal like that. "I may not like the reason, but I have to admit I like your style." Once I got over the initial shock of what he'd said the rest of his words sunk in, "Current and future Winchesters?"

A wry grin sent all that seriousness packing, "Well, you never know."

"Huh, good point, I guess. Thanks, I was kind of wondering what was going on with that. It just seemed too weird that nothing had caught up to me. I mean, I've got hex bags in the house and I wear them when I go out but still."

"No problem, I've been wanting to threaten him with something like that for years. I'd do it too if something happened to you or Coyote and a demon was involved. Still would."

"I know." Sure, he'd put it out there that he wouldn't bring me back but in the end, family was still family. I was actually a bit relieved to know he'd let me go. I didn't want to go through all that again and I know Coyote wouldn't want me to come back from the dead either. It's not the natural order and every time we'd fucked with that things got worse.

Things got quiet after that for a few minutes, there was something on his mind. "What?" I asked.

"Dean, I want you to promise the same thing. I go, let me stay gone. Same for Coyote, something happens to her, you have to be willing to let her go too."

Fortunately, she'd already extracted that promise from me about six months in. She threw her beliefs at me, told me that if she died then woke up and I was standing over her she'd kill herself if she had to. She believed that once Shamans died their Spirits and knowledge added to this collective consciousness other Shamans could tap into, that to bring her back to life would deprive others of her gifts. Seeing her work I couldn't ignore the fact that something was there, helping her. So I agreed, as hard as it was, I knew if I'd said no we'd never work out. Agreeing to that one made this one a little easier, but not by much.

"Her and I dealt with this a few months back, I told her yes. It's part of her beliefs and I won't mess with those."

"And me?" He asked.

It hurt, God did it hurt but it was the right thing to do and very often right isn't easy. "Yes, you go, you stay gone. We've both been through enough. The thing that takes you out though, that gets to suffer."

He shook his head, "No, Roy handles that. Not you."

"Sam! Why?"

"Same reason you didn't want me to keep hunting after you went to Hell. Roy can handle it and not lose himself, you can't."

"You want me to sit back and let someone else take out the thing that kills you? No way."

He slowly turned his head to look at me and I got a taste of how he must of looked threatening Crowley, "I want you mourn then move on, like normal people do. Our family's lost enough looking for revenge. Understand?"

"I..." For some reason, for all I know my Warrior Spirit was making itself known, memories of Coyote started crowding out my thoughts. Not just recent ones either, older ones, all the times it'd hurt to leave and choose the life over her, the night I walked out and headed off with Sam to do the Trials and thought it was the last time I'd ever see her. All the times I'd had a chance to let him go and be with her. Then, and I hesitate to call it a vision since I'm not Shaman, we'll go with a rough imagining of the future started playing out in my mind. Sam was dead, her and I were arguing and I was walking out, leaving her in tears, again. The last thing I heard from her was, "You can't come back this time. I won't do this again." I stood there, looking at Baby's door. Then it faded. Was it worth it? Was killing some monster that someone else could take out worth losing her for. Time seemed to stop for a second, not just outside of me but inside, my brain was quiet, even my emotions had somehow faded. I saw everything so clearly, "Understood. Roy or whoever takes care of it." It wasn't worth it. Living like that, the darkness, the emptiness, I never wanted to be that person again, ever. I'd been like that for too long already.