March 14, 1930
Dawn,
I have no idea when this letter is going to get to you, or if it's even going to make it to you at all, but I figured it was worth a shot to keep you from worrying. If this does, in fact, get there after Dad and I have gone missing, I want you to know we're okay. We're stuck in New York, in 1930, but we're okay. Lana's here with us, along with the freaking pirate of all people, but we're all okay. A little freaked out and very, very ready to be rescued, but okay. And did I mention we're okay?
I know I shouldn't tell you not to worry, but I'm going to do it anyway. I know you guys will figure something out and get us, it's just a matter of time. Dad and I are trying to see what we can figure out on our end here, but those of you still in 2008 are the ones with the technology, so I'm willing to bet you'll find the answers before we do.
Please, please stay away from the angels. I don't want anything to happen to you while I'm not there to protect you. If Dean is still in 2008 with you, can you keep him away from the angels as well? If you can keep him sane until we get back, that would be good too, but I have a feeling that might be a more daunting task than I should ask of you.
I miss you so, so much. When we get back, remind me to tell you about bonding with my dad. Getting stuck with him has been kind of an eye-opening experience.
Now for the fine print. If, for some reason, you can't find a way to get us, I want you to know that I love you and I'm pretty sure I always will. You're the best thing that's ever happened to me, and I just want to make sure you know that.
Once we get rescued, I can say that to your face, so feel free to get to it. I miss you.
Love,
Sam
March 14, 1930
Peter,
I don't know if this is going to work, but the chance that this letter will get to you is enough for me to try. If this does arrive after Dad and I have gone missing, I just want you to know that I'm okay. We're not hurt at all, just stuck in New York, in 1930. Lana's here, and so is Barbossa, and Dad's with me, so I'm not alone either. Of course, that doesn't mean we wouldn't all welcome a rescue. I don't suppose you've copied time travel from anyone, have you?
If you can, please make sure Dean isn't out doing anything stupid. He gets kind of crazy when I'm in trouble, and I don't want him to get hurt while I'm not there to have his back. And don't go doing anything dangerous yourself either. I know - self-healing, blah blah blah - but as usual, I don't care. I want you to be safe, no matter what.
I'm kind of amazed at how much I miss you. Please take care of yourself. Hopefully I'll see you soon to make sure you're doing it in person again.
-Sam
Dean's letters arrived in a stack about an inch thick. The postmarks started in New York, but there were letters from nearly every state in the pile. According to the dates, the letters were written weekly, then monthly, and then more sporadically, right up to the early 1970's, when the letters abruptly stopped. Some of the letters were more like diary entries, where Sam caught Dean up on everything he and their dad were doing, telling him what they were hunting, where they were going, and what kinds of historical events were going on. Other letters were more emotional, as Sam wrote about how he was feeling, how much he missed everyone, how much he hated being stuck, and sometimes, how much he hated everyone for not rescuing them. Many of the letters asked Dean to watch over Dawn, or check in on Peter. But no matter what the content was, all the letters ended the same way:
I miss you, Dean. Please take care of yourself.
- Sam