They never talked much about 1996, though it was a year filled with noteworthy events; Endeavor 10 went into space that year. The flip phone debuted, and Garth Brooks became a phenomenal force in music. There was a record-breaking blizzard in the East that winter, but luckily John Winchester and his two teenage sons were holed up in Anaheim where they missed it.
Sam was 13 - Dean 17 - in 1996. It was a year just like any other, except that Dean had a close call that January when a shapeshifter pitched him off a rooftop on South Street. For a while, John thought he'd lost his oldest son, and indeed, Dean's rehabilitation from his injuries was slow and often tedious.
But aside from this, 1996 would have been just another year in the life of the Winchester family. Rougher, maybe, and a bit more of a challenge, but not too far off this side of normal.
Except that it wasn't.
Instead, ruffled by his son's close call with death, John Winchester decided, in 1996, to turn over a new leaf, rent a nice house, and take a day job at a nearby gun shop. He installed Sam in the local school while Dean continued to heal from his massive and debilitating injuries.
And in April of that year, John met Leslie Benigan. She was a gun enthusiast who frequented the shop John managed regularly, and in the beginning, she made him laugh.
Leslie was tall and slight with darling red hair that had never seen a bottle of dye. She kept it clipped in a stylish bob that matched the rest of her elegant appearance. The woman was two years younger than John, liked the same kind of music, and loved guns and classic cars. She worked as a freelance writer for several small, local publications - covering mostly topics about guns and hunting. And she was head-over-heels for the gruff gun seller with the two teenage boys.
Once John realized he felt the same way, he introduced Leslie to Dean and Sam, and two of the three hit it off amazingly well. Dean and Leslie bonded instantly over weapons and hunting techniques, cars and music.
Sadly, the relationship between Sam and his father's girlfriend wasn't as immediate. By all appearances, Leslie tried hard to bond with the youngest boy while Sam resisted every attempt. After that first week, he was moody around her, withdrawn, and tried hard to avoid spending any time alone with the woman who'd managed to capture his father's heart.
And the more Sam resisted, the more stressed John's relationship with his youngest became. John wanted his own happiness, that much was true. But more importantly, he wanted a normal life for his boys.
He thought Leslie could give them that if Sam would just allow it.
What he didn't realize was that the woman with whom he'd fallen in love had once had a thirteen-year-old son, and she hadn't liked him any better than she liked Sam. She found children that age to be awkward, clumsy and entirely too needy, which was how her own son, Nicholas, had ended up a ward of the state a week before his fourteenth birthday. She saw Sam as an inconvenience - an obstacle to be removed so that her life could continue on, unaffected.
When John and Dean were present, Leslie was the perfect stepmother-to-be, cooking for Sam and offering to help with his school projects. When the two were alone, she went out of her way to be … less nice.
They didn't talk much about 1996, because both John and Dean were wracked with guilt about what happened that year.
It was the worst year of Sam's life, and the youngest Winchester nearly didn't survive it.