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Timeline of Every Anecdote from Dean's Childhood in Supernatural

winc*sties this is not for you. i'm a survivor of familial CSA and i don't want to see you in my notes.

This is super open to feedback and suggestions if I missed something. This also includes a few quotes and things from a couple of the tie-in novels where they don't conflict with canon.

Looking for a Full Canon only timeline? I got you!

Content notes: death, child abuse, alcohol

1983

Dean is 4

John & Mary used to call Dean their “little piglet” because he liked to eat so much. [1]

Dean played T-ball. [2]

Mouse Trap is Dean's favorite game. [3]

Mary would feed Dean tomato-rice soup when he was sick. [4]

Mary would sing "Hey Jude" as a lullaby. [5]

Dean really likes Mary's meatloaf. He doesn't know she gets it from Piggly Wiggly. [6]

Between May and November John and Mary had a fight and John left home for a few days. [7]

November 2 - Mary Winchester dies, Sam is 6 months old.

November 6 - Mary Winchester's funeral. Her uncle arranges a headstone even though she doesn't have a body. [8] John Doesn't go. [9]

Before November 16 – They're staying with friends, Mike and Kate. [8] John Meets Missouri. [11]

November 16 – John walks out of Mike & Kate's. Takes boys to Julie's. Goes to see Missouri. Julie gets killed. They leave Lawrence. [12] “Got the hell out of Lawrence. If I never go back, it'll be too soon. Not for Dean, though. The first thing he wanted to know was when we would go remember a home [sic]. But we don't have a home anymore, Dean. The sooner you get used to that, the better.” [13]

John leaves a box of pictures in the basement of the house. [14]

November 20 – Dean sees John kill a shapeshifter. [15] “Dean walked out of the roadhouse right when I put the final bullet into the shape-shifter's head. And he said, 'Why'd you kill him, Dad?'” [16]

November 21 – Boys are with Pam & Bill in Elgin. John's first night away from them. [17] “Here's what I wish I could say to Dean – Your brother's too young to understand any of this, but you're beginning to. And that scares me. Since your mother died, I've seen unspeakable things, and now you've seen them and that's my fault.... Until then, I can only pray that you're strong enough to look after Sam. One of us has to be.” [18]

November 25 – John meets Pastor Jim. [19]

November 29 – John gets the boys from Elgin & leaves. [20]

December - Dean still hardly talks. He never budges from John's side – "or from his brother. Every morning, Dean is inside the crib, arms wrapped around baby Sam. Like he’s trying to protect him from whatever is out there in the night. [21]

December 11 - Sammy has finally started sleeping through the night, and now that Dean shares a bed with him, he’s out like a light as well. [22]

December 25 - "a crooked two foot tall plastic tree, a bunch of junk food stuffed in the stockings, and a pile of sports equipment for the boys… football, basketball, soccer." [23]

December 29 - “Dean hasn't been the same since he saw me kill that shape-shifter. I don't know how to talk to him about it. He's not even five years old. Most kids his age don't even have a clear idea what death is, and he's seen it up close and personal. What do I say to him? How old does he have to be before I tell him the truth?”[24]

13.21 (okay this is technically in a dream of Sam's)

http://www.supernaturalwiki.com/John%27s_Journal_(diary_entries)

14.17

5.13

12.02

5.16

2.04

"John's Winchester's Journal" by Alex Irvine

http://www.supernaturalwiki.com/John%27s_Journal_(diary_entries)

John's Journal

1.09

John's Journal

http://www.supernaturalwiki.com/John%27s_Journal_(diary_entries) & John's Journal

John's Journal

1984

Dean is 5

“I realized I can't leave [Dean] in school... I know he should be able to run around with other kids, who don't know how to field-strip the Browning. Well, Dean doesn't either, yet. But he's learning. He's got a talent for guns. I can see it already. And he'll need it.” [1]

May 2 – John meets Daniel Elkins. [2]

May 17 - “Sammy took his first steps yesterday. He walked toward Dean, then fell flat on his face and started crying. Life is tough, kid. Do I sound like a proud dad? I am.” [3]

1-3. John's Journal

1985

Dean is 6

January 24 - “It's been more than a year since he saw me kill a shape-shifter. He doesn't talk about it anymore. And he's stopped asking when he's going to go to school. Maybe this year, now that he's a little older, now that he knows a little more about things. I've been teaching him. Not the worst stuff, but enough so he knows that there are things that go bump in the night.” [1]

September 7 – Dean's first day of school. [2] “He asked on the way in whether kids in school learned the same stuff he'd been learning. I had to tell him that maybe it wasn't a good idea for him to talk about Dad's job on the playground. He came home on the top of the world, and he brought me worksheets with the names of the different parts of a fish...” [3]

November 2 - “Dean saw something on my face, or maybe it was just that he knew what day it is. When I got here, he came up to me and asked if I'd had a tough hunt. I couldn't talk for a minute.” [4]

November 14 – John takes Dean shooting the first time. “Took Dean shooting. If he's big enough to try to comfort me, he's big enough to start learning the tools of the trade. I only let him fire the .22, but he is a deadeye marksman. My drill sergeant would have taken him over me in a second. Times like this, I sure am proud of my boy. I have a feeling it will be different with Sammy. Maybe he's just too young to show it, but I don't think he's got the same kind of killer instinct.” [5] John takes Dean out shooting for the first time, using bottles as target practice. According to Dean, he "bullseyed every one of them." Dean remembers this story as him being “6 or 7." Dean cites this story as one of the fonder memories of his father. [6]

Rufus spent the whole year being nice. It was the worst year of his life. [7]

1-5. John's Journal

6. 2.06 7. 7.10

1986

Dean is 7. “For his seventh birthday, I took Dean shooting again. He wanted to fire one of the big guns – that's what he called them. I let him shoot the Browning, but I steadied his hands. Sammy wanted me to help him make Dean a card.” [1]

Dean starts having a crush on Daisy Duke. [2]

April 16 – Bill Harvelle dies. [3]

May 2 - “Sammy is three years old today. We celebrated with ice-cream cake. He was still wearing most of it when he fell asleep. Dean's sleeping too, the two of them in the same bed. The room only has one bed. I'll sleep on the floor... Some nights it's enough to watch them sleep, and know that if they start having a nightmare, I'll be right there to stop it.” [4]

September 5 – Dean starts second grade. “I watch him like a hawk. He makes me swear that I'll take good care of Sammy before he'll go to school. God, I love that kid.... Sammy's a very different kid. He hasn't taken to the idea of hunting bad guys, and he's still too young to really understand what it means to avenge his mother.” [5]

November 2 – “Dean watches his little brother like a hawk every minute, with an expression on his face that says he's willing to die to keep Sammy safe. [Mary] doesn't know how it tears me up inside to see that expression, and to know that it's there because I have drilled it into Dean that Sammy is his responsibility. He's eight [sic] years old, and I've told him his brother's life is in his hands. Mary, I didn't have any right to do that. But what else could I do?” [6]

John began the masked vampire case - looking into killings and kidnappings along Route 77. [7]

John's Journal

11.13

2.06, 2.14 & John's Journal

John's Journal

15.20

1987

Dean is 8

January 24 - Dean's school has a party for him then John takes them to Chuck E. Cheese's. [1]

John takes Dean and Sam on a donkey ride at the Grand Canyon. Dean’s donkey is very flatulent which Sam finds very funny. [2]

May 2 – John has to pull Dean out of school because a demon knows where they are. “Dean understands.” [3]

May 17 - “I'm starting to figure out you can move a kid from school to school every month, and the schools deal with it because they have to. A part of me wonders how the kids deal with it. But sons have to be soldiers. And soldiers adapt.” [4]

July 13 – A hunt goes bad for John in Portland, Maine. “We were almost to the New Hampshire state line and I'd told Dean a little about what had happened, because I was so frustrated and ashamed that I had to talk to someone. Sammy was asleep the whole time. Then Dean asked me one of those killer questions that little kids come up with. 'Dad,' he says, 'Won't the manitou go after other people now?' That's a hard thing to face. Not that he asked the question, or that he was right, but that he had a better sense of right and wrong than I did.” [5]

November 2 - “Dean asked me today what she looked like. He never talks about her on any other day but this one. I couldn't even show him a picture, so I told him what you tell a boy who asks about his dead mother. I told him that she was beautiful and kind and she loved him and Sammy more than anything in the world.” [6]

Dean has begun hunting. [7]

John's Journal

8.21

John's Journal

11.08

1988

Dean is 9

January 24 - “We're on our third move, so he might not finish third grade. He calls himself the New Kid all the time. He's been to three schools already this year. Who knows how many more.” [1]

May 2 - John is hunting a Shtriga in Wisconsin when he leaves Sam and Dean alone in a hotel room. Dean gets bored and goes out and comes back to find the Shtriga attacking Sammy. John returns in time to scare the Shtriga off. [2] “I could blame Dean, but it's my fault. There's enough blame to go around. I missed the kill, and I left Dean watching Sam, and he couldn't pull the trigger when he needed to. I haven't taught him well enough. If he is weak like that again, my boys will die... but what kind of father am I to put my a nine-year-old boy in a situation where he might have to kill to protect his brother? I'm the kind of father I have to be. I'm the kind of father who teaches his boys that no man or monster can kill their mother and get away with it.” [3]

They know Pastor Jim by this point. [4]

Dean and Sam (5) were playing dress up as Batman and Superman and jump of the roof of a shed. Sam breaks his arm and Dean took him to the E.R. on the handlebars of his bike. [5]

May – John knows Bobby by now. [6]

December 5 - “Dean's teacher called to tell me that he got a subscription to Weekly World News, and had it delivered to school. How is he paying for it? I could ask him, but he's already too sharp to give me a straight answer. And I could force him to, but there's no point. If that makes him feel more at him in this world...” [7] (Dean later misremembers the name of the newspaper.[8])

At some point before now Dean is given his first beer by Fred Jones in Salt Lake City. [9]

John's Journal

1.18

John's Journal

1.18

9.15 (mentioned again in 11.08)

John's Journal

2.03

8.08. He also apparently gives Sam his first beer too but it's unlikely it was this same time?

1989

Dean is 10

January 24 - “Dean turns ten today. Regan out of office.” [1]

Dean knows how to drive. [2] “Not young like I was when he actually taught me how to drive.” [3] (If Sam learned to drive by 9 (see 1992), it stands to reason Dean would have learned at least that early if not sooner.)

“When I was 10, I got my first B&E from borrowing some family's pay-per-view so I could watch the cage match between you and the Tower of Power.” [4]

May 2 – Sam turns six. John sends him to kindergarten. “He's such a different kid than Dean. Quiet, watchful. He's learned that there are things to fear in the world, but where Dean wants to fight them, you get the sense that Sammy watches, learns.” [5]

July 4 – Dean & Sam are in a day camp. Staying nights with Pastor Jim – camping in his yard. “On the fifth day of the camp, Dean was canoeing through an easy rapids on the Blue Earth River. Things went bad. Dean swore to me when he came back that he'd seen something – only he said 'someone' – capsize the canoe. I didn't think about it too much... until the next week when another canoe went over and the counselor paddling it died.” John pulls them from camp. [6]

Dean: "You couldn't been more than 5— you just started asking questions. How come we didn't have a mom? Why do we always have to move around? Where'd Dad go when he'd take off for days at a time? I remember I begged you, "Quit asking, Sammy. Man, you don't want to know.... I just wanted you to be a kid... Just for a little while longer. I always tried to protect you... Keep you safe... Dad didn't even have to tell me. It was just always my responsibility, you know? It's like I had one job... I had one job..." [7]

November 2 - “Today I overheard the boys talking about her, about her death. Sammy's old enough to be asking hard questions, and I think that's making Dean think about some things that he'd put away until now. He's a tough little kid, Dean. Like me. But he's also like me in the way he holds things in. Now his little brother is asking him things and he's got to figure out a way to protect Sammy while Sammy's questions put him through the emotional wringer all over again.” [8]

Bobby takes Dean to play catch instead of “practice with the double-barrel” as John had instructed Dean. In the flash back Rufus guesses the year is around 1989. “No, we didn't shoot rifles, as a matter of fact. We threw a ball around. He's a kid, John. They both are. They're entitled.... Yeah, I know I ain't their dad.” Bobby hangs up and throws the phone down. [9]

John's Journal

http://www.supernaturalwiki.com/Origins_1

11.04

11.15

John's Journal

2.22

John's Journal

7.10

1980s General

(i.e. there isn't a specific date mentioned for this but I'm guessing from context that it happened in this decade)

Sam sticks army men into Baby's ashtray. [1]

Dean sticks Legos into the vents. [2]

Dean eating all of Sam's Halloween candy sometime. [3]

John taking them to see World of Wrestling. Sometime before Dean is ten. Dean calls it “one of the nicest things” John ever did. Sam remembers John getting drunk. [4] ("The Hangman": "He was Dad's favorite. Anytime that noose would come out, Dad would be on his feet. It was one of the few times I ever saw him actually happy.")

John takes Dean fishing. When Dean tells Jack, Jack feels from his tone that it's his happiest memory of John. [5]

Dean telling Sam a stupid joke to distract him from ripping off bandaids when he was little. [6]

The first beer John shared with Dean tasted like "crap". [7]

Sam's memory of Thanksgivings: “We had a bucket of extra-crispy and Dad passed out on the couch. [8]

Dean: "I always wanted to be a fireman when I grew up." [9]

Dean says he believed the TV ads about Sea Monkeys having families [10]

Dean mentions a babysitter, Mrs Chancy, who was obsessed with the TV show Dynasty [11], which ran until 1989 when Dean was ten. This could be a lie he's just telling a kid to get him to open up about his babysitter though.

"Alright, here we go. John Winchester's famous cure-all kitchen sink stew. There you go. Enough cayenne pepper in there to burn your lips off, just like Dad used to make." [12]

"You used to read to me, um, when I was little, I— I mean, really little, from that— from that old, uh... Classics Illustrated comic book. You remember that? ... Knights of the Round Table. Had all of King Arthur's knights, and they were all on the quest for the Holy Grail. And I remember looking at this picture of Sir Galahad, and, and, and he was kneeling, and— and light streaming over his face..." [13]

Dean says soft rock always put Sam to sleep. [14]

Dean talks about learning 101 different ways to make Mac 'n Cheese for Sam at a motel in Scranton while John was off hunting. "ketchup for spice, hmm? Uh, tuna, hot dogs, fluff marshmallow mix." [15]

5.22

12.11 & 14.04

11.15

14.17

15.01

15.20

5.16

1.22

5.06

8.21

7.13

10.12

1990

Dean is 11

January 24 - “Dean turns eleven today. He asked for his own gun, and I got him one. A Seecamp LWS .32 automatic, the smallest gun I could find that offered any kind of stopping power. Dean and I poured silver slugs for it ourselves and we loaded it with alternating silver and Winchester hollow-points. He's got it in his pocket now.” [1]

January - John is injured on a hunt in Windom, Minnesota, and goes to the hospital, where he meets Kate Milligan. [2]

May 2 – They've moved around enough that Sam is behind in school. John thinks he should do more like home teaching. “I'd ask Dean to do it, but there's only so much you can pile on a kid. Having Sammy's life in his hands is enough for Dean; he can't be responsible for home-schooling Sammy too.” [3]

September 29 - Adam Milligan is born. [4]

At some point Dean makes a sawed off. He's in sixth grade. [5]

Dean tries burgers from a seaside shack in Delaware that become his favorite. [6]

John's Journal

4.19

John's Journal

4.19

3.03

4.22

1991

Dean is 12

February – Winchesters go to Albuquerque for a few months. Dean “even talked about wanting to play basketball this spring, but I'm not sure he's serious. I think he's taking cues from me, talking about everyday stuff when I try to keep us in one place. Then when we're on the road again, all he can talk about is hunting.” [1]

March – Sam played a sunbeam in the school play and talking about a science project to enter into the school fair. John working construction. [2]

March 17 – The kids play soccer. [3]

April 1 – John quits his job. Mrs Lyle kidnaps Sam – taking him to a regional science fair but not. “Dean came through. I don't have any words for how proud I am of him. His brother's under some kind of spell, there's a giant monster made out of train parts coming after me, and he has the presence of mind to find the journal and read the exorcism out of it. I almost lost both of my boys today.... How am I going to explain to Sammy that we're not going back to school?... To top it all off, I had to give Sammy a sharp lecture on not talking to strangers. While I was on the phone with Bobby, he just got out of the car and went up to a black Seville. I read him the riot act – Dean too, since he let it happen and it's his job to watch Sammy. All Sammy would say about it was that the guy wanted to know where we were going.” [4]

April 7 – At Bobby's. [5]

April 18 – Silas, friend of Bobby's tells John Sam is special. [6]

April 19 – John taking Dean deer hunting. “It's out of season but the Dakotas are lousy with Deer and Dean needs to pull a trigger to sharpen him up.... The hunting trip was nearly a disaster. Dean missed the shot. I sent him after the buck, a beautiful twelve-pointer, and he dropped the gun when he tripped on the trail. Then out of nowhere comes Sammy, who picks up the gun and lays that big boy out. A seven-year old... well, almost eight. Then he tells me that the deer had taken Dean's gun, and that Sammy had to protect him.” Sam got a ride from the Black Seville to the trail. They go back to see Silas. Dean & John leave for an hour but they see the Seville. Go back to Silas'. John leaves Dean outside with Sam on the porch but John finds Silas butchered inside. [7]

Dean to Bobby: “You used to take us hunting. Remember? Dad had a case, he'd just dump us on you. Shoot, you must have taught us most of the outdoor tracking we know.” Bobby: “Yeah, what I could get to stick. I never could get you little grubs to pull a trigger on a single deer.” Dean: “You’re talking about Bambi, man.” Bobby: “You don't shoot Bambi, jackass. You shoot Bambi's mother.” [8] (This interaction isn't directly referencing the story above but it adds context, I think.)

April 20 – John has kidnapped Anderson, from the Black Seville, stolen the car and Dean killed Anderson. “My oldest son is blooded.” [9]

December 25 - Sam (8) and Dean are at a motel in Broken Bow, Nebraska. John is hunting while Sam and Dean spend Christmas alone together. Sam reads John's Journal and finds out that Mary's death was supernatural, monsters are real, and that John hunts them. He confronts Dean, who confirms it. Sam gives Dean an amulet. [10] John suspects Sam has been reading the journal. Says he left them presents. Dean stole night vision goggles from the gun show in Amarillo to give to John from him & Sam. [11] “They're both starting to act out a little, because we're apart so much. Sam gets resentful and has trouble keeping his temper. Dean tries to fix everything and keep us together as a team.” [12]

John's Journal

7.09

John's Journal

3.08

John's Journal

1992

Dean is 13

January 24 – they celebrate at Mama Janer's in Flint, Michigan. [1]

March 30 - “I thought the lesson was learned back in Wisconsin, but the same thing almost happened again. I left the boys next at the beach in Two Lakes State Park and went looking for a skinwalker, and then it was Ichi all over again. Only this time the skinwalker took on the appearance of a park ranger it had killed, and nearly got the boys to come with it because they trusted the uniform. I still can't completely trust them on a hunt. I took it down, and lit into the two of them. Especially Dean. I have to be hard on him because one of these days I'm not going to be around, and he's the one who's going to have to look out for his brother. He's a badass, though. I thought I was tough when I was thirteen, but Dean would have kicked my ass six ways to Sunday.” [2]

John buys a Playboy featuring Anna-Nicole Smith, eventually both boys end up reading it. [3]

June - Sam tells John he is afraid of the monster in his closet and John gives him a .45. [4] Sam sleeps with it under his pillow and sleeps soundly for 5 nights in a row. [5]

Sam wants to go hunting with Dean. Dean says John said no. John calls to ask Sam to come. [6]

Sam learns to drive when he's nine. [7]

John's Journal

7.22

1.01

John's Journal

11.08

John's Journal (mentioned in 1999)

1993

Dean is 14

January 24 – Dean goes to the movies with "girlfriend" (according to John) Katie. “Quite the ladykiller that kid. Like I was at his age.” John thinks Dean is like him and trouble. “He's like me. If i'm not careful with him, by the time he's twenty he'll have left a trail of kids and arrests warrants all over the country.” [1]

January – Motel Baba Yaga case. Dean says, “I was babysitting you when I was your age”. Sam says "I'm pretty sure that's illegal." Dean sees the nest, a pile of dead kids and has "nightmares about it for the longest time." [2]

May – Sam has been on a soccer team. He had a game and John took him bow hunting instead. They need to learn weapons because “there are demons after Sammy. He needs to know how to fight them, and Dean needs to know how to protect him.” [3]

Summer - John takes them hiking in the Rocky Mountains. One day he fills packs for Sam & Dean and takes them up a mountain and leaves them around dark, telling them to wait for an hour then try to find the way back and that he doesn't expect them for days. They find the packs are full of mostly useless supplies. John says it's a lesson not to trust anyone. [4] (DM me if you want the full quote. It's really sad.)

December 25 – Joplin, Missouri. Sam & Dean give John a book on theosophy which John guesses they stole. [5]

John's Journal

15.16

John's Journal

"Witches Canyon" by Jeff Mariotte, 195-198

John's Journal

1994

Dean is 15

January – Dean helps John “take out a spirit haunting a grocery owned by an Indian family in Erie, Pennsylvania.” It wasn't as simple as burning bones because of different traditions. [1]

May 2 – Sam asks for a computer for his birthday. John gets him a Macintosh Performa. “Looks like Team Winchester just took a big leap ahead when it comes to gathering information.” John mentions Bobby helped him get fake credit cards. [2]

Summer - Sam and Dean spend part of the summer being looked after by Donna, a babysitter (and maid at the Mayflower) in Housatonic, Massachusetts, while John hunts. One time John is gone for two weeks. It is the summer before Sam enters 6th grade, and he assigns himself a summer reading list. Dean possibly has a crush on Donna. [3]

October - They are living In Bismark (North Dakota?). Sam has a crush on Andrea Howell & has a really bad experience at her Halloween party, throwing up. Sam hides in the woods until Dean comes and gets him. [4]

Sam still believes in the Easter Bunny until close to here. [5]

John's Journal

5.12

14.04

10.12

1995

Dean is 16

January 24 – Montana hunting a werewolf with bows. John says he'll let Dean take the lead on the hunt the next day. [1]

January 25 – Dean does very well. Good shot. [2] Dean's first Werewolf. Sam doesn't go to the body burning. "So. I pick up this crossbow. And I hit that ugly sucker with a silver-tipped arrow right in his heart. Sammy's waiting in the car, and uh, me and my dad take the thing into the woods, burn it to a crisp. I'm sitting there and looking into the fire, and I'm thinking to myself, I'm sixteen years old. Most kids my age are worried about pimples, prom dates. I'm seeing things that they'll never even know. Never even dream of." [3]

Dean spends two months at Sonny's Home for Boys after being caught shoplifting. [4]

April 20 - Dean's award for New York Wrestling Champion. [5] John is in Oklahoma City hunting. [6]

Sam spends all of his time on the computer or arguing with John. “He wants to be in one place, live a normal life. The older he gets, the more he wants it. But the older he gets, the more I'm going to need him to help on the hunt. He's got to understand that.” [7]

November 13 – Sam's soccer team won division championship. John writes that he's proud of him and that he'll keep the trophy. [8]

Sam later talks about how John was upset with him for wanting to play soccer instead of learning bowhunting. [9]

November 24 - Sam has his first traditional Thanksgiving dinner at his crush Stephanie’s house. He has been attending a school called McKinley for two weeks. [10]

John's Journal

2.03

9.07

John's Journal

3.03 & John's Journal

1.08

5.16

1996

Dean is 17

January 24 – John takes Dean shooting. Then sends him to hunt. “I've let him take the lead before but I've always been there to back him up. This time he's on his own. Partly it's a test, and partly I wanted some time with Sammy. Should be no problem for Dean. Ghosts of two nuns haunting St. Stephen's Indian Mission in Riverton, Wyoming. Simple salt-and-burn mission. Nuns in love with each other, then discovered. Killed themselves. We scoped the situation out, figured that something must be left behind that's now a focus for the haunting. Bible, rosary beads, some small article that's hidden somewhere in their room. I figured Dean would take care of it no problem, but I still stayed close by with Sammy.... Dean took care of the nuns just like I thought he would, but I don't think I'm going to be sending him on any more solos soon.” [1]

Sam finishes sixth grade a year late. He's mad about it. [2]

July 4 - Dean and Sam set off fireworks in a field and almost burn it down. [3]

At some point when Sam was 13 he ran away for two weeks while under Dean's watch in Flagstaff, Arizona, living off pizza in a cabin and befriending a dog he called Bones. Dean scoured the whole town looking for him and worried he might have died, and John was furious when he found out. [3]

John's Journal

5.16

1997

Dean is 18

January 24 – John gives Dean the Impala. “I've taught Dean a lot of what I know about working on cars, which was everything until 1983.... He knows I'll still be driving it, but he's a man now, and since he's already made his share of kills, this was the only right of passage I could think of. He goddamn well better take care of it.” [1]

When he's 13, Sam briefly wants to be a magician. [2]

May – Sam has been having strange dreams. “Plus now that he's hitting adolescence, he's a giant pain in the ass. Dean just chased girls and snuck around with beers in his coat pockets.” Sam just shuts down or wants to argue. [3]

June 16 – John claims Dean graduates high school & gets a diploma. John says Sam will be graduating when he's nineteen and will be mad about it. [4] But Dean didn't graduate high school. He got a GED. [5]

Summer - The Winchesters hunt a werewolf. [6]

November - Sam and Dean attend Truman High in Fairfax, Indiana, for 3 or 4 weeks, while John is on a hunt that was originally supposed to be 2 weeks but ended up taking longer than expected. Dean is in 12th Grade. It is the third school they have attended since September. [7]

John's Journal

4.12

John's Journal

5.01

4.13

1998

Dean is 19

Sam is a mathlete. [1]

Summer - While John and Dean are off hunting a Kitsune, Sam stays in Lincoln, Nebraska, and does research for them. While there, he meets a girl and has his first kiss - only to discover that John and Dean's hunt has circled back on him. [2]

May – John feels Sam is shirking his duty. Dean and Sam don't get along as well. [3]

July - Dean goes on a solo "five states in five days" road trip, but ends up spending most of it in Cicero, Indiana, with Lisa Braeden. In the meantime, John & Sam "tie up a hunt" in Orlando, Florida. [4]

Dean meets Rhonda Hurley, she makes him try on her pink, satin panties and he likes it. [5]

At some point they spend time with Travis, the hunter. [6]

4.04

7.03

John's Journal

3.02

5.04

4.04

1999

Dean is 20

January 24 – Dean in Ohio. “Hasn't called in a couple of days. Tracking a possible poltergeist. He's supposed to call in every night. Mission discipline is critical.” [1]

John's Journal

1990s General

Dean trying to cook Winchester Surprise on a hotplate with food (baloney and sliced cheese) that it seems Sam shoplifted in the rain. John gets home and throws it out. [1] In Lebanon John tells Sam he remembers this and apologizes to Sam for it. [2]

Sam and Dean visited the Cleveland Botanical Gardens on a field trip. [3]

Dean going to CBGB "way underage" and John coming to get him. [4]

Hunting the chupacabra in Mexico. Sam is an olderish teenager when he says this happened the year before. [5]

John making Dean be bait, [6]

Dean used to live on “Nerve Damage” (“10 times the legal limit of caffeine”) as a kid. [7]

Escalating prank wars? [8] Sam mentions a time Dean put superglue in his toothpaste. [9]

Could be 80s too: Dean: “Remember that wreath Dad brought home that one year?” Sam: “You mean the one he stole from, like, a liquor store?” Dean: “Yeah, it was a bunch of empty beer cans. That thing was great.” [10]

Sam performing in Our Town. [11]

Sam talks about having to make his own dinner as a kid. [12]

14.11

14.13

5.16

10.09

11.10

14.14 production draft. Corroborated by 1.20. Putting this in 1990s and not 1980s is very generous imo.

13.08

1.17

15.06

3.08

1.09

5.06

2000

January 1 – Dean has a terrible hangover. Immobile. John is also hungover. [1]

January 24 - Dean is 21. “I'd buy him a beer if I thought it would be something new. He's also old enough to buy his own guns now. I tried to raise him right, and it looks like I did. He's a scam artist, a ladies' man, and an absolutely loyal son. He knows what's right and doesn't hesitate to do it. I'm proud of him. Now that he's hunting on his own I don't see as much of him, but I know he's out there. When I call him on a job, he's right there every time. I've spent the last sixteen years afraid that I was going to screw him up somehow. Maybe now I can forget about that.” [2]

May 2 – John buys Sam a Mac for his birthday. [3]

1-3 John's Journal

2001

Dean is 22. He's away from John in Arkansas. [1]

May 2 – Sam & John aren't getting along. “He hunts when we need him to, but he's never committed himself the way Dean did. Dean's never known any other way to live, or if he has, he doesn't act like it. He's playing the role he was born to play.... I've given [Sam] more slack that I ever gave Dean.... Dean never even thought about college. We used to joke about it once in a while.” John wants to convince Sam not to go to college. Sam helps hide their trail of credit cards. [2]

Sam smokes weed maybe. [3]

John's Journal

11.19

Pre-2002, 2000s General

Sam & Dean driving 1,000 miles for an Ozzy show. [1]

Driving two days for a Jayhawks game. [2]

John catches Lee and Dean 'wasted' on a hunt. [3]

John plays Dean and Lee “Good Ol Boys” before hunts. “Listen up boys this is real music. [4]

Sam used to try to get him & Dean to do 'honest work' rather than hustling pool.[5]

The Las Vegs annual trip. [6]

Sam ran tech for a production of Oklahoma. [7]

5.22

15.17

5.22

7.08 (this seems like a stretch, imo)

10.05

Post-2002, 2000s General

Dean sleeps with Annie. [1]

Dean sees Lee while Sam's in college. [2] Possibly the 'cult thing in Arizona' 'what that thing did to that family, those kids.' Because Lee does one more job after that in Texas and retires.

At some point Dean hunts a Vetala and learns they usually hunt in pairs. [3]

7.19

15.17

7.11

2002

Dean is 23. John imagines he feels physically invincible. [1]

John gives Sam the "hunting is life; you can't have connections" speech. [2]

March 8 - Sam says he's leaving hunting to go to Stanford University. John says if he leaves to stay gone. [3] “And now he's going to college? He can go to hell, is where he can go.” (“Dean has always responded to discipline because he believes in the mission”) [4]

June 13 – Sam graduated high school (he's 19). John thinks he's mad it took him a year longer. [5]

August 31 – Sam leaves & John tells him to stay gone. [6]

September - Adam Milligan meets John Winchester. [7] (This could be any time from now til 2003 but I think it would be now because John will want to feel he can replace Sam or do something right.)

John's Journal

4.19

1.01, 1.20

John's Journal

4.19

2003

Dean is 24

January 24 - “I was twenty-four when I married his mother. Sorry, kid. Every boy has to cut the apron strings sometime, and for you it's not going to be until we kill off a supernatural entity that seriously needs killing.” [1]

Dean dates Cassie Robinson in Athens, Ohio, for a few weeks, while she finishes up her senior year of college (at Ohio University). Cassie breaks up with Dean after Dean tells her about hunting. [2] It lasts less than two months. [3]

May 2 – Dean & John are leaving Ohio. John overhears Dean on the phone talking about Sam. John notices Dean has been in a rough mood. [4]

June 13 – Dean hears about a succubus in Brooklyn from Richie and heads out quickly. [5]

June 21 - Dean is involved in a hunt for the father of Cole Trenton, in Nyack, NY. [6]

October 9 – Poltergeist case in Kittanning, PA. [7] John mentions that he's been visiting Palo Alto but not like seeing Sam. [8]

John gets taken from this year into the future in "Lebanon." He is sleeping in the Impala and Dean calls him and he tells him he'll be back soon. [9]

John's Journal

1.13

5.11

John's Journal

John's Journal, 3.04

10.02

1.04 & John's Journal

John's Journal

14.13

2004

Dean is 25

End of June – John visits Palo Atlo & sees that Sam has a girlfriend. [1]

September 29 - John takes Adam to a ballgame for his 14th birthday. [2]

John's Journal Book

4.19

2005

Dean is 26, dude.

January 1 - “When I was twenty-six, I'd been married for two years and had a toddler. Dean's never been with a woman for more than a couple of weeks at a time. I've prevented him from being a father.” [1]

January 24 – John mentions he's been telling Dean more about the demon stuff he's learning from Bobby. [2]

Summer - John teaches Adam to drive using the Impala (this is after John gave Dean the car for his 18th). [3]

September 29 - John buys Adam a beer when he's 15. [4]

October 3 - John cuts off contact with Dean (John is in Jericho, Dean in New Orleans). [5]

October 28 – John leaves journal in Jericho & goes after demon. [6]

End of October – Dean comes to get Sam.

Dean: "I must have stood outside your dorm for hours... because I didn't... I didn't know what... What you would say. I thought you'd tell me to... to get lost or get dead. And I don't know what I would've done... if I didn't have you. 'Cause I was so scared." [7]

John's Journal

4.19

1.01 & John's Journal

John's Journal

15.20

General Comments

(i.e. just quotes and things that are too general to place at a specific time. i've sorted them roughly into themes but all of these themes are also present in incidents above.)

Dean says he's been wanting John and Mary back together since he was four. [14.13]

John's absence

Sam: "You remember the poltergeist in Amherst? Or the Devil's Gates in Clifton? He was missing then, too. He's always missing, and he's always fine." [1.01]

Dean mentions how John would dump him and Sam at Bobby's. [7.09]

Toni Bevell saying about John's drunken rages and weeks of abandonment. Also pointing out that Dean & Sam didn't tell Mary about it. [12.21]

Sam says John would be gone for weeks at a time and "he wasn't exactly a monk." [4.19]

Sam says John "was not around much." [11.05]

Sam talks about worrying when John & Dean would be out on a hunt and he wouldn't hear from them for days. He thought about what he would do. [11.18]

John's drinking

In the pilot Sam comments that John is likely missing because he's drinking. [1.01]

Sam comments that a dad bringing their kid to a wrestling match to distract them while he drinks seems familiar. [11.15]