John Winchester

John was an ordinary child up until his father Henry Winchester's disappearance. What became of John after that moment is never specified, though he likely hardened from the lack of his real father.

As part of the United States Marine Corps during the Vietnam War, John was undoubtedly a capable fighter by that point, strong and fearless though he retained, at least until Mary's death, a gentle, loving heart. He moved to Lawrence seeking a better and more stable life, and he became devoted to Mary, even though her parents were against the match.

John was naive to the supernatural world and despite marrying a hunter, he never learned what lurked in the shadows until Mary's deal with Azazel led Azazel to come into their home one night. Mary was set ablaze on the ceiling of Sam's nursery and John's life was forever changed.

Many of John's friends have described this period as difficult and rough for John, who had two young sons to tend to. Without a home, he relied on old friends for shelter until he picked up the habit of living on the road or in cheap motels. He was regarded as deluded and a little disturbed during this time, as John was beginning to find out about the supernatural.

His years as a soldier helped to prepare John a bit in what he had to face, and he was able to train his sons to become skilled and tactical fighters. However, coupled with the loss of his wife and the stress of dealing with monsters on a regular basis as well as his desire to avenge Mary at all costs made him neglect the boys. He also put high expectations on his elder son, turning Dean into the perfect little soldier who was to protect Sam at all costs.

John was aware of his neglect, and he may have tried to compensate by shielding his sons from most of the things he hunted. Although John expected Sam and Dean to be ready to face a few horrors, Sam and Dean were nevertheless left in the dark about many creatures. John's head strong personality, molded from his years of killing and hiding and searching for Azazel, made it hard for him to form any lasting relationships.

John's two lovers, Tara and Kate, rarely heard from him again after their hook up. Bobby Singer, a close friend and occasional caretaker of Sam and Dean, wanted to shoot John dead with a shotgun over an unspecified offense. Other friends of John also became distant, leading to years of no contact.

Eventually, John found out about Azazel, about a weapon that could kill the demon, and some of the demon's plans. John's wish to foil the demon's plans drove John to want Sam dead should Sam become evil, eventually passing it on as a final order to his good son Dean and putting a wedge in the brothers' relationship.

John was, for most of his life, met with misfortune that could easily have turned John into a self-loathing and self-deprecating man. He had few friends he could share secrets with, and for the most part John lived a rather lonesome life filled with nightmares come to life. His dream of a happy family, which he could not have in his childhood, was never made real for more than a few years and Mary, the love of his life, was forever gone after her demise for the rest of John's life.

During his brief reunion with his family, John was very happy to be with his sons again and expressed pride in them for saving the world when told of their exploits. He was also happy to learn that his father did not truly abandon him and seemed content to learn of his legacy as Men of Letters. John also showed genuine remorse for what he had put his sons through, taking the time to make amends with Sam as well as admitting to Dean that he hoped for Dean to get a normal life and a family after they killed Azazel, though he also accepted Dean's admission that he had a family with a smile, showing he was truly happy for his sons. However, the thing that really elated him was being with Mary again and he shared a loving embrace with her. As noted by his sons, John was more happy than they ever saw at dinner, most likely because he had his whole family with him. Though he forgot the event after returning to the past, John could not help but crack a smile at the experience and implied he believed it occurred.