April 2, 2000
Dear Sam,
It's been awhile since i last wrote to you. I have been really stressed with life lately. I got fired and I've been applying everywhere. I'll try to write more frequently.
Love, Dean

April 3, 2000
Dear Sam,
I met someone today. I was at Starbucks and they wrote Hi on my cup. All i know about them is that their name starts with C. I'm not sure which barista it is yet though.
More on that later.
Love, Dean

April 7, 2000
Dear Sam,
I went to Starbucks today again. I think i have an admirer. They said "Good to see you again -C"
I don't know if it is flirting or not, but if it is the barista i think it is then i am definitely interested.
Love, Dean

April 22, 2000
Dear Sam,
Sorry i haven't written in awhile. I got sick and i was in the hospital. Dad tried to call you but you never answered. I had pneumonia, but i got better. I just got out of the hospital yesterday.
Love, Dean

April 30, 2000
Dear Sam,
I went back to the coffee shop again. There was a note on my cup again.
"It has been awhile. -C"
I've been watching the baristas but i still cant figure out which one is writing the notes.
Love, Dean

May 4, 2000
Dear Sam,
I have a job interview today. I stopped by the coffee shop before hand to get some energy. My admirer noticed ;)
"Dressed up today? You look good. -C"
It is just what i needed before a big interview.
Love, Dean

May 9, 2000
Dear Sam,
I haven't been sleeping well lately. I got the job, and i have been working night shift.
I got an extra shot in my coffee at Starbucks today. Apparently i looked tired, so C put one infor free. I still don't know who C is, but i have a hint.
More later, i have to sleep.
Love, Dean

May 13, 2000
Dear Sammy,
My admirer has a name. Cas
That's a guys name, yeah. So i might be a little gayer than originally planned.
"The next one is on me. -Cas"
Am i crazy for being excited?
Love, Dean

May 18, 2000
Dear Sammy,
My admirer is fucking hot. He wrote a note and pointed out which barista he was. Oh my god he has the prettiest blue eyes. I can't help but blush when i see him.
Am i in love?
Love, Dean

May 22, 2000
Dear Sammy,
I got his number. I am so excited. I wish you could meet him. He is so sweet.
Love, Dean

May 28, 2000
Dear Sam,
Cas asked me out today. Of course i said yes. Turns out his full name is Castiel Novak. Apparently its an angelic name. It suits him.
Sam i wish you would pick up the phone. My life is finally getting good and i want you to be apart of it. I'm sorry for whatever i did.
Love, Dean

May 30, 2000
Dear Sam,
Dad died today. The DOCTORS said he had a by LizardSales"HEART ATTACK in his sleep. The funeral is Monday, but i know you probably wont come.
I found his journal in the closet. He talked about you a lot. He regretted abandoning you all those years ago. He always wanted to take it back.
Sam please. I need you. I don't know if i can go on alone.
Cas says hi by the way. He looks forward to meeting you at the funeral. I haven't told him that you wont be there.
Love, Dean

June 15, 2000
Dear, Sam
Dad has been dead for about two weeks and i haven't heard from you at all.
I got fired again. I wont be able to pay for my apartment, but Cas said i could move in with him. Sammy i love him. But i'm scared. Please, little bro. Answer me.
Love, Dean

June 30, 2000
Dear Sam,
I don't see why i am still writing. You don't answer. I guess it is just habit.
Cas is amazing. I think you would really like him. He has 2 brothers, a little sister, and his dad abandoned him like ours did. We have a lot in common. I'm in love with him. I might be moving too fast, but i want to tell him. I've never done this before. Sammy please come home.
Love Dean

July 5, 2000
Dear Sam
I got to watch the fireworks with Cas last night. I met his family too. We ate watermelon and had a picnic. His family is nice, and his brother Gabriel reminds me of you. His little sister is adorable. She looks almost exactly like Cas.
Sam i want you to meet them. Please just answer me
Love, Dean

July 30, 2000
Dear Sam,
Me and Cas moved to a bigger apartment. It has two bedrooms, so if you ever want to visit you have your own bed. Cas seems bothered by something. I don't know how to ask. I need help, Sammy. i need you.
Love Dean

September 15, 2000
Dear Sam,
I found why Cas was upset. Turns out he is being bothered at work but another employee. I am going to kill them if they lay a finger on him. I really need some backup, man. I told Cas that he should tell the boss but he is scared. We might have to move again.
Oh i got another job. I work for a car company, fixing cars.
Love, Dean

October 1, 2000
Dear Sam,
Anna, Cas's little sister moved in with us today. I think you would like her. She is like a daughter to me. It turns out that Cas basically raised her.
Cas quit his job a week ago. The person who was bothering him hit him and Cas just gave up. We have decided to move to Texas soon. That is where Cas grew up, so it will be good for him.
Love Dean

November 2, 2000
Dear Sam,
Today is the anniversary of mom's death. I tried to call you, but of course you didn't answer. I am thinking of taking a trip back to Kansas and visiting her. Cas said i should go. I don't want to go alone but Cas can't come with me.
Love dean

December 31, 2000
Dear Sam,
I bought you a Christmas present. I have a secret. A big one
I am going to proposed to Cas tonight at midnight.
I hope he says yes
Love Dean

January 2, 2001
Dear Sammy
He said yes! We are officially engaged now! Anna is moving out soon, she is going to the same college you are going to. I told her to keep an eye on you. She said she would.
Cas wants to adopt a kitten. I told him no, our apartment complex wont allow pets.
We might move again.
Love Dean

February 14, 2001
Dear Sammy,
I am sick again. The doctors don't know what is wrong. I am getting worse, but i am hiding it from Cas. He is so upset, i don't want to worry him anymore than i need to. We got a kitten. We are hiding it from the lndlord right now, we cant afford to move yet.
Anna said that she saw you on campus. She said you looked good.
Love Dean

March 10, 2001
Dear Sam,
It is cancer, Sam. I have cancer. The doctors are trying everything they can to try and slow it down. Cas is worried sick, he is constantly crying. Sammy i am scared. I don't want to die.
Please answer.
Love Dean

April 30, 2001
Dear Sam,
I am not going to make is, Sammy. We can barely afford the treatments. They are slowing it down , but there is a chance i wont make it. Best case scenario i get five more years.
We moved to a small apartment for a few months until we find something more stable. This is going to be expensive.
Love dean

May 12, 2001
Dear Sammy,
It is slowing down. Sammy i might make it. Cas got a job and his brothers are helping fund my treatments. I'm losing my hair, Sam. It's all falling out. Cas says he doesn't care, he still loves me.
We decided to have the wedding in October. I'll send you an invite. I really want you to come. It is incredibly important to me.
Anna said she talked to you. I know you are getting these letters. Please reply.
Love Dean

May 20, 2001
Dear Sam,
I might recover. The DOCTORS say it is almost gone. Cas is delighted. He smiled for the first time in a month when i told him.
I love him so much, Sam. You need to meet him.
Love Dean

May 30, 2001
Dear Sam,
Cas bought me a wig. It is almost the same colour as my old hair. My cancer is gone! The DOCTORS said there is only a 5% chance that it will return.
My hair has already started growing back and i am getting stronger.
Dad died a year ago. Sammy pick up the phone.
Love Dean

July 27, 2001
Dear Sam,
It has been awhile. I hear you started dating a girl, Jessica. Anna told me she saw you two together. I would love to meet her. You should be graduating soon, right? Will you come home then?
Love Dean

September 11, 2001
Dear Sam,
Did you hear the news? The twin towers were hit in New York.
Castiel's brother, Michael was there. They haven't heard from him. He is presumed dead. Cas is in tears. I don't know how to comfort him.
Sammy i need you. Now more than ever.
Love Dean

September 13, 2001
Dear Sam,
Cas got a job at the coffee shop here. It is a fun experience. I like to go in there and get coffee. He leaves sweet notes on it, just like when we met.
We are getting married soon. I sent you an invitation. Anna is going to be the flower girl.
I need a best man. Will you be mine?
I'll save you a seat.
Love Dean

October 20, 2001
Dear Sam,
Today is the wedding. I've been waiting two days for you to show up. It looks beautiful in the church, Cas looks amazing.
I have to go now, i am about to get married.
I miss you, little bro.
Love Dean

November 1, 2001
Dear Sam,
The wedding was beautiful. You should have been there, Sam. But i don't blame you. I just got back from the honeymoon.
It was super fun. We went to New York. I loved it, Cas has always wanted to go there.
I really miss you, Sammy. But I've given up calling you.
Love Dean

November 14, 2001
Dear Sam,
I'm sick again. Not cancer. But i don't know what it is. Cas is worrying himself sick too. I can see it in his eyes.
Love Dean

November 22, 2001
Dear Sam,
Anna is pregnant. I'm not sure if you know or not, since you go to school with her. She isn't ready for a baby, so she is going to let us adopt her! I'm so excited, Sam.
Love Dean

December 27, 2001
Dear Sam,
It is a girl! We are going to name her Mary Samantha Novak-Winchester. The Sam part is after you. Hopefully one day you can meet her.
Love Dean

March 18, 2002
Dear Sam,
The cancer is back, Sam. I haven't told Cas yet. The doctors don't know how.
Just when things are getting good. Anna is 4 months pregnant and Cas is already painting the nursery.
The doctors say i have to start chemo again. I don't want to, Sam. I am scared. I need you, man.
Love Dean

June 14, 2002
Dear Sam,
The baby is due in two months. She is supposed to come on the 13th. Anna is worried the date is unlucky. She is really superstitious.
I am doing good. I started chemo again.
Cas is worried but he doesn't know the whole truth.
Sam, the doctors gave me a year to live. The cancer has spread too far for them to completely get rid of it. I can't tell Cas. It will break him.
Love Dean

July 24, 2002
Dear Sam,
Anna had her baby on the 22nd. She was almost a month early. She is really weak right now but oh Sam she is beautiful. She has the same eyes and Anna and Cas. Her hair is so soft. She has the prettiest smile.
Sam i wont get to see her grow up. I wont get to raise my baby girl.
She is allergic to cats, so we had to give our cat to Anna. She will take good care of it.
Love Dean

August 31, 2002
Dear Sam,
It has been a long time since i have seen Cas cry. I told him today, about me dying. He didn't say anything, he just cried. I tried to hold him, but he wouldn't let me touch him. I am worried Sam. What does this mean for us.
Love Dean

November 1, 2002
Dear Sam,
Mary was a little bumble bee for Halloween. You should have seen her, Sam. She was adorable.
Cas is pretending that i never told him. When i try and talk to him, he brushes it off. I think he is in denial.
I am getting sicker. I feel it, Sammy. I can feel it in me.
I don't know if i have much longer
Love Dean

December 12, 2002
Dear Sam,
I can barely hold the pen now. I've lost my hair again, i don't know why i still take chemo. It is pointless. It is all pointless Sam.
Why am i still here? I am only causing problems. Money problems mostly. Cas cries every night. He wont let me touch him.
I told him about my letters to you. He said that if i can't write anymore then he will write for me.
It hurts to breathe, Sam. I can feel myself dying. It hurts. It hurts so bad.
Love Dean

January 25, 2003
Dear Sam Winchester,
Hello. This is Castiel Novak-Winchester, your brothers husband. I know you do not know me, but i am begging you.
Dean is sick. He told me that he had a year, but i know he is lying. I can see it in him. He is growing sicker. He doesn't have much longer.
He needs you, Sam. He needs to see you. I do not know what happened between you, but he is dying. It is a hard thing to admit, but i must learnt o be strong about it.
I am begging you. Please pick up the phone.
Yours Truly, Castiel Novak-Winchester

February 14, 2003.
Dear Sam,
I am sorry that i haven't written as often lately. Being sick really takes a toll on you. Mary is doing so great. Oh Sam she is beautiful. I wish you could see her.
I can't hold a pen anymore, so i am having Cas write this letter. He told me that he wrote you last month. He said you didn't reply.
Love Dean
p.s. Hello again, Sam. Dean doesn't know i am writing this on the end of his letter, so lets keep this a secret.
I do not know what kind of man that you are, and i apologize for what i am about to say, but you are a horrible brother. Your brother is dying, Sam.
He has maybe a few months left at most. You need to see him. At the very least, pick up the phone. Your brother needs you, and the way he talks about you, you are a good brother. So man up and come see him.
-Castiel

Febrary 20, 2002
Dear Sam,
Please reply,
Love, Dean

April 22, 2002
Dear Sam Winchester,
Dean died. on the 19th. I am sorry to write this so late, but i couldn't bring myself to pick up a pen.
His last words were to tell you he is sorry.
The funeral is of the 25th. I hope to see you there.
-Castiel Novak-Winchester

February 26, 2003
Dear Sam,
I saw you at the funeral. Well, at the cemetery. I know it was you, Dean used to show me pictures of you. I am glad you showed up. Dean would be happy. I know he is smiling down from heaven.
I wish we could have talked some. You should meet Mary. She has Dean's personality.
Come by sometime.
Yours Truly, Castiel

March 14, 2003
Dear Sam,
I found a note in Dean's Impala. It was a sealed envelope addressed to you. I have attached it with this letter.
-Castiel
[Attached letter]
Dear Sammy,
Hey little brother. You might not be able to read this. My handwriting sucks now. Look, bro. This is the last letter i will write you.
I am going to die. And i have accepted it.
I guess i should make a will. Most everything is going to Cas of course. But you get my car. It was always yours. Take care of it. But NO DOGS. You know the rules.
Look Sam. I am so sorry for what i did. I abandoned you. I left you and went with dad. I regret it every day. I'm not going to leave you like dad did, without ever apologizing. I love you, man.
You will probably get this letter after i died. I left it in the car where cas is sure to find it.
Please go visit them after i die. I can't be there for Mary to grow up, but you can. Please, Sammy. I am begging you. Do it for me.
Tell Cas i love him. I love him more than life itself. I know he knows, but i just want to make sure.
I miss you, Sam.
Love Always, Dean Winchester

RIP Dean Winchester