The day after the fire, Bobby had calls early to excuse the two boys from school, and he drives Dean to the park- it's too far to walk. Dean waits all day, but Cas doesn't show up or answer his house phone. The same thing happens the next day, or the next, or the one after that. It's like a ritual; Bobby picks the boys up from school and drops them off at the park at three every day. Dean stays at the park every day, doing his homework or playing a game on the weekends. No matter what, Dean spends all of his free time at the park where he met Cas.
Sam comes with him often, silently doing his homework on the same bench as Dean. He doesn't comment when Dean's head snaps up at a new arrival or mention Dean's barely audible whimper when it's not Cas. He helps Dean when he gets stumped because Sam's a really smart kid and Dean is really proud of Sammy and he knows he'll go far in life. Sam is also growing like a weed, which Dean gives him a ridiculous amount of grief over.
John, their father, falls into alcoholism before Dean even leaves Junior High School. He's not abusive, but he is loud and angry. He eventually loses his ability to hold a stable job. Bobby sends him to rehab, multiple times, but John always relapses. Bobby is granted custody of Sam and Dean.
By the time Dean hits high School, he has a reputation as the bad boy and the dark broody one, and there's a rumor floating around that he can kick someone ass six ways from Sunday, which he can because Bobby taught him and Sam how to defend themselves. He doesn't dissolve the rumors, but he doesn't confirm them either. He becomes close friends with Jo Harvelle and Ash. Jo and Ash live with Ellen- Jo's mom, who scares the pants off of Dean- at the Roadhouse which is Ellen's bar; their house is on the second floor. Sam is friends with a sweet girl named Jess (who Dean thinks has a crush on Sam and vice versa) and a girl named Ruby who is a bitch (Dean thinks she also has a crush on Sam). The only people who know where Dean disappears to all hours of the day are Sam, Bobby, and Jo. Not even John knows where Dean goes every day. Jo has never met Cas, but he knows they'd be amazing friends.
When Dean becomes a sophomore in High School, his life is thrown for another spin; new evidence is found in the case of their house fire. The evidence being; John Winchester was a cheating bastard who had an illegitimate son. Kate Milligan had left an anonymous note for the Winchester boys (and Bobby) so they go to the Police Station. They go, curious. The woman confesses to killing Mary Winchester with the hope of getting John to return to her, but she can't live with the guilt anymore. She pulls out a gun and Dean only has enough time to pull Sam's head into his chest as the woman blows her brains all over the police station.
Sam knows what happened; he knows, but Dean saw. The blood haunts Dean in his sleep and Bobby gets his a therapist, trying to work through it. He goes through therapy for months. But They still had one problem; Adam Milligan. Technically, he was Sam and Dean's brother, but it was proof that John had not, in fact, been the loving loyal father they though he was before their mother had died. Adam hadn't seen what his mother had done at the police station, but when he learns what she did to Mary he cries. Bobby takes Adam in because he is technically a Winchester. Dean is uncomfortable, but he accepts that Adam is a part of their family. Sam is more than enthusiastic to have a younger brother, but Dean knows Sam will always chose him when it's important. John, however, hates Adam.
Adam isn't allowed at Cas' park. Only Sam and Jo are allowed to accompany Dean there. No one else comes to the park because of Dean's phantom reputation. Adam does settle into school very nicely though, making a few friends that Dean doesn't know and he doesn't bring them to Bobby's house. John and Dean's relationship-what little there was- withered instantly with the knowledge Dean had gained from Kate. Dean hates his father for being immoral and a hypocrite. He disobeys John at every turn, Sam close behind. The two older brothers know Adam hates John just as much, but they know he'll never speak out of turn for fear of being thrown out, so they speak up for him. They do talk about it though, how Adam feels about their whole situation.
When dean becomes a Junior in High School, fate decides to play with Dean again. His father had pestered Dean into going with him to the Bank with some talk about something being wrong with Dean's trust fund- the one his mother had made secretly. Dean is grumbling the whole way, but the engine of his father's Impala mutes it out. The Impala was his second favorite place as a child. It always calmed him down. As a child it was the quickest way to get him asleep. They never got to the bank.
John, in one of his sober spells, had an excellent reaction time. But someone could only swerve so quickly when a large semi-truck comes at you from oncoming traffic. He swerved, but the semi clips the end of the Impala, sending it into a tailspin. John throws his right arm out in front of Dean, his fatherly instincts reacting immediately. When they skid to a stop, the first thing John does is ask Dean if he's alright. Before Dean can answer, a truck slams into the driver side, sending them flipping over the orange monster. The Impala lands on her top; all windows are obliterated and the engine looks mangled.
John unbuckles himself, hitting the floor hard. Dean goes to do the same but moving his arm cause pain to shoot through him like lasers. John looks at his son with unfiltered concern. He gently helps Dean out of the seat buckle and onto the floor. John kicks his door open after three attempts while Dean's is missing completely. Dean gets out of the car, holding his arm close. The Winchesters quickly limp off the road near the small forest (more like a collection small collection of large trees) bordering the freeway. Dean leans on the tree for support, legs feeling like Jell-O. John pulls out his cell phone and calls 911. Before anyone can do anything else, an explosion shakes everyone not even a quarter mile down the road. Dean hears more screeching tires before something solid collides into him; solid, but not a car.
Dean looks up and screams. The sight will have him in therapy for years to come; John was pinned to the tree Dean had been leaning on with a small four door sedan. John groans in pain, and Dean is by his side in seconds begging him to hold on. Dean knows to call the police, but he doesn't want to leave his father alone in case…Dean shakes himself and scrambles to his father's discarded cell, where the dispatcher is calling for someone to answer. Dean tells her where they are and what happened while he checks the driver and his two small children for signs of life. The man driving is dead, and one of his children is badly injured and bleeding, but the younger girl is relatively fine and crying for her dad and brother. Dean tears at his shirt to try and stop the bleeding, wishing and wondering why he can't do anything for his father. Dean has taken plenty of first aid classes-something Bobby insisted on when they'd gone to live with him- and he's smart enough to know his father is dead and his brain just hasn't caught up yet.
Dean goes back to his father when he knows the boy won't bleed out without him. It's registered in his brain what's happened, but seeing the pain his father is in breaks Dean's heart and he would give anything to trade places with his father. Dean knows his father's chances are slim to begin with-infinitesimal in fact- but the longer the paramedics take, the lower Johns chances are getting. That doesn't stop Dean from begging his father to stay with him; he promises to be good, he promises to get Sam to behave too.
It takes twenty three minutes for the ambulance to find them. While they wait, John tells Dean about how much he loved Mary-still loves her-and how much he messed up when he cheated on the only woman in the world he actually cared for. He tells Dean how he loves Sam and Dean-Adam too, but he'd never even known about Adam, he never got a chance to meet the boy on one of his good days. He never got a chance to tell Dean how badly Mary's death affected him, but he sees now that he wasn't the only one effected and he's sorry. No one should lose their mother so young, John knows because he lost his dad that young. John holds his sons hand, and tells him how much he loves Dean and he is so proud of his champ- and Dean cries harder because John hasn't called him that since his mother was alive- and no matter the choices Dean makes, he will always love him, and he will always be proud. There is nothing in this universe that could ever make John hate Dean and he wants Dean to know that. John is so happy that he was able to give the world the gift of Dean Winchester; and Sam and Adam, though John wishes once more that he'd been able to actually meet his youngest son.
It takes twenty three minutes for the ambulance to find them, but it only took John Winchester nineteen to bleed to death.