Dear Bobby…

By Teallover

Sam explains his reasons for what he did. An alternative route out of season 2. Warning, this story does contain character death. But it's got a happy ending, so maybe that will lessen the blow;)

Dear Bobby,

Hi, it's Sam. I've asked the motel desk clerk to mail this for me if I didn't come back. Just in case, you should also be getting a delayed email saying the same. You know me, I just wanted to cover all of my bases. If you're reading this, I'm sorry to tell you that I'm—well dead. It's ok though, you should be used to it by now;)

I'm sorry for the really bad joke. You know I love you like an uncle, always have, always will. I just wanted to lighten the subject a little, because otherwise, it's all very complicated. But that's the Winchester way, isn't it.

Please don't be mad at me, Bobby. I did what I had to do. No more deals with devils either—we're finished with that. I don't want you or anyone else to ever do that again. Their deals are crap to get out of. Which leads me to why I'm dead right now. I have a confession to make.

I killed Dean.

I didn't bring him back.

It was the hardest thing I ever had to do.

Maybe I should back up a bit and tell you what happened.

I'm sure you remember the deal that Dean made in exchange for bringing me back to life. I couldn't find a way out of it. I couldn't let him go to hell for me, Bobby. That's for eternity. He didn't deserve that. He's done too much good to ever deserve that kind of suffering.

I summoned the reaper that nearly got him in the hospital. I figured she'd still be smarting over the one that got away, so I knew she'd be all too happy to come and take Dean to where he belonged. I know that's not hell.

I had already decided that if I couldn't save his life, I was at least going to save his soul. That's some choice, huh. Do nothing for a few days and let the hell hounds take his soul to hell for eternity, or help him into the next life.

I wish there was a third option. But there wasn't.

Two days before his time was due to be up, I drove Dean out into the woods and we said our goodbyes. He wanted to separate then because he didn't want me anywhere near when the hell hounds came for him. He made stupid jokes. He made me laugh. He acted like it didn't bother him. He tried to do what he always does, make me feel better. That's what big brothers are for, right?

I held on to him with everything I had, knowing that it was the last time I would ever hold him and have it returned. We were both afraid, and I couldn't tell if the trembling was from him or me.

I just knew that it felt good when he wiped away my tears and started rocking me like he used to do when I was a kid and had a nightmare.

I don't think he even felt it when I slipped the needle in his arm. The rocking just slowed and his arms fell to his sides. His eyes closed peacefully and I couldn't stop crying.

Dean was dead.

And I killed him.

To make a long story short, I saw the reaper. She kept her end of the deal. I know she took Dean where he deserved to be, which was most certainly not hell.

I did ask her one question though. I wanted to know if committing murder would send me to hell when I died. I wasn't bothered by it if it did, but I just wanted to be prepared.

Surprisingly, she threw me a bone. She was just so happy that she finally got to collect the one that got away, that she gave in a little.

She said that saving a life for unselfish reasons puts you in a position to make it to the "good place"—her words, not mine Bobby.

Too tired and frustrated to figure out her riddle, I huffed at her angrily. "So does that mean that I'm not going to hell for murdering my brother?"

"What do you think?"

"I think you really enjoy jerking us Winchesters around."

She laughed in agreement. Can you believe that? A reaper. Laughing her ass off at me. Then she did that fading from sight crap—full of smoke and mirrors and the whole nine yards--and said in this mystical voice, "a soul is worth even more than a life."

So I guess that means I'll be ok.

At least until the crossroads demon finds out what I did. I have no doubt that she's going to kick my ass. I went through a lot of spells and trouble to make sure that she didn't figure out what I was up to before hand.

I'm going to meet her tonight, which is when Dean's time would have been up. And I know I'm not coming back.

You've done so much for us over the years, and for that I thank you with all of my heart. But I have one last favor to ask of you, my friend. If there's anything left. Please salt and burn.

PS. I already took care of Dean's body. His ashes are in the glove box.

Love Sam.



Sam was leaning under a tree, absently picking at the ground beneath him. He looked down at his hands to find the brilliant yellow flowers in them. He raised an eyebrow and questioned out loud, "Why am I picking daisys?"

Dean swaggered over and grabbed his arm, hauling him up with a smirk, "Because up here, you just can't deny those girlish tendencies."

Sam flung himself onto his older brother, wrapping his arms around the shorter man. "Dean!"

Dean smiled, patiently allowing the hug for five, four, three, two, one… "Ok, get off me."

Sam pulled back, grinning madly. "You're not mad at me?"

"No, why would I be? I'm livin' the life up here. Oh, Dad says hi by the way. He couldn't come. He's got a date," Dean told him and waggled his eyebrows.

"Wait, Dad's here? Cool. And what do you mean he's got a date? With who?"

"Mom of course, you idiot. They've been acting like they haven't seen each other in decades…which they haven't, but still—" Dean shuddered. "Anyway, took you long enough, Sasquatch."

Sam shrugged, "Yeah, well, I was a little bit busy."

"Oh, that reminds me. So what did you do with my deliciously lovely corpse?"

Sam's grin grew even wider. "Flame broiled, extra crispy."

Dean smacked him then grinned. "And yours?"

"I uh, I'm hoping that Bobby will take care of that."

"And how is he supposed to know, college-boy? Cause I'm guessin' you didn't tell him what you were up to."

Sam bristled defensively, "I sent him a note."

"Yeah, what's it say? Dear Bobby, please salt and burn…"

"Something like that," Sam admitted with a smirk as he strolled along side of his brother. He suddenly noticed the double-edged sword swinging from Dean's hip. "Hey, why do you have that?"

The shorter man stopped abruptly, turning his body so that the sword would no longer be easily visible behind his legs. His face burned red with guilt. "Have what?"

Sam gestured around him and raised an eyebrow. "The sword Dean? I thought all of this meant we were done with hunting?"

Dean sighed loudly before shrugging. He could never fool his brother, so he may as well tell the truth. "You can, Sammy. But we left a huge mess down there when the gate was opened. So I asked them if I could go back and help. They said yes, on occasion. In fact, I was headed down to annoy you when I got word that you were coming up here to annoy me instead."

Sam bit his lip hesitantly. "But what if something happens while you're down there. What if—"

"Awe, Sammy. Don't worry. There's no danger of me not coming back. I'll have a human form again, so I could be hurt or killed. But then somebody just hits the reset button, I come back up here to relax and rejuvenate. Then I can go back down and kick some demon butt again. It's a sweet deal."

Sam nodded in understanding, so Dean reached out and gripped his shoulder before turning to walk away. "So I'll see you around little brother."

The older man got no further than 10 steps before the younger of the two called him back. "Hey Dean?"


Sam pointed to the sword, "You got another one of those?"

AN: I'm thinking about continuing with Dean and/or Bobby's point of view. Or maybe their new adventures. What do you think?

See, it wasn't as sad as you thought it would be…right? ;)