Supernatural may have ended, but it lives on in its devoted fanbase and reruns. Sam Winchester was the more empathetic and kind of the Winchester brothers, and he had an entirely different life planned for himself when audiences first met him in season 1. Unfortunately, Sam's life didn't turn out the way he thought it would, and he certainly made mistakes and had regrets.
Season 1 Sam would love certain things about the way his life turned out, and he'd certainly hate other aspects, like his addiction to demon blood and the torture he endured from Lucifer over the years. Sam's life wasn't perfect or easy, but he ultimately got a normal life, which is what he'd always wanted.
10 Hate: All The Loss, Blood & Gore
Season 1 Sam got away from hunting for a reason - he didn't like the job one bit. The sacrifice, blood, gore, and danger wasn't appealing whatsoever, and Sam wanted nothing to do with it. That's why Season 1 Sam would be heartbroken at the fact that that chapter of his life wasn't quite closed.
He and Dean lost plenty of people over the years, including their father, Bobby, Jo, and Charlie, and even their enemies-turned-allies, like Crowley and Rowena. Sam is strong, but he endured a lot of hard times and terrible things to become as strong as he is.
9 Love: He Never Completely Became The Hunter That Dean Was
Sam was always the more sensitive and understanding of the Winchester brothers. Dean never really understood his brother's actions in that regard and often teased Sam for it. However, for Sam, it was important that he didn't become the ruthless hunter that both his father and brother were - it just wasn't who Sam was, or wanted to be.
In later seasons, Sam grew more ruthless, but he still sought to see the good in everyone, most notably with Jack, Lucifer's son. Given all the agony Lucifer put Sam through, it was a big deal that Sam showed such kindness and compassion for Jack, even after Jack had inadvertently killed Mary.
8 Hate: His Time As Soulless Sam
Season 6 was a particularly dark time for Sam. He may have been alive once again, but without his soul, he wasn't really himself. He became more ruthless and cunning, and definitely had no love or empathy for anything or anyone else and compared to who Sam really was, this Sam was a robot.
Sam was capable of unspeakable things, and season 1 Sam would hate to learn of the things he'd done without his soul, including brutal killings and allowing Dean to be turned into a vampire.
7 Love: He Patched Things Up With John
Sam always had a difficult relationship with his father. They never saw eye-to-eye, and as Sam grew older, his resentment for being dragged around the country and trained to be a hunter increased. Sam wanted a normal life, and when he left for Stanford, John told him to stay gone, feeling that Sam was abandoning their family.
Sam's and John's relationship still struggled up until John's death, and it wasn't really until "Lebanon," when Dean inadvertently wished for John back, that Sam and John patched things up. Nonetheless, Sam finally got the chance to say what he needed to say and to bid his father goodbye, which meant the world to him.
6 Hate: He Didn't Get Out Of Hunting Entirely
Season 1 Sam's dream was to finish school, marry Jess, and become a lawyer. He wanted a normal life, without any hunting. No more crossing the country looking for evil things, no more family business - nothing. That's why he'd be heartbroken to learn of what his fate entailed, given he would lose Jess and become a hunter once again to avenge her death.
Even after her death is avenged, Sam always remains stuck in the hunting world, having to save his brother, the world, or something of the like. Finale Sam probably isn't crazy about the veered detour his life took compared to his original plan, but season 1 Sam would have definitely hated it.
5 Love: He Reconnected With Dean
When Dean came to Stanford asking for Sam's help in tracking down their father in the pilot episode, their relationship was strained, at best. They hadn't seen each other for a while, and there was obviously tension, given Sam's determination not to get involved in the hunting world, and Dean's insistence that their life wasn't all bad.
However, Dean was there when Sam lost Jess, and the two would continue to bond and be there for one another over the years as they faced obstacles and tragedy, with some good times in-between, together. Season 1 Sam would be glad to know that finale Sam had his brother back and that their bond was stronger than ever.
4 Hate: His Demon Blood Addiction
Sam had a major addiction problem with demon blood. When Dean is suddenly brought back to life in season 4, it doesn't take long for him to find out that Sam didn't abide by Dean's wish that he not mess with his abilities. Sam consumed demon blood to make himself stronger and more powerful, with encouragement from Ruby.
Season 1 Sam would be horrified that he ever used his abilities in that manner, given he was freaked out enough when he found out he had such abilities in season 1. Season 1 Sam wouldn't be too keen on the idea of having a relationship with a demon, either.
3 Love: Jess's Death Was Avenged
Jessica was Sam's everything. He planned to marry her one day and live a normal, hunter-free life with her. Unfortunately, those plans came to a screeching and tragic halt when he returned home after helping Dean track down their father in the pilot episode, as Jessica was killed in the same way, and by the same thing, that had killed his mother.
That event spurred Sam into becoming a hunter once again to avenge her death, which was accomplished when Dean killed Azazel in season 2. It doesn't bring Jessica back, but Sam could rest a little easier knowing that the thing that took his beloved girlfriend from him had paid for it.
2 Hate: Everything Lucifer
Out of all the villains Sam and Dean faced, Lucifer is the most memorable. Lucifer was evil in every way, and always took pleasure in messing with Sam. Sam truly struggled in season 7 with hallucinations of Lucifer once Castiel broke the wall in his mind that was protecting Sam from the damages his soul sustained in Hell.
Season 1 Sam was overwhelmed by Azazel. Lucifer was an entirely different ballgame when it came to the villains on Supernatural, and it's something season 1 Sam would've detested, and something finale Sam doesn't look back on with fondness.
1 Love: He Eventually Got A Normal Life
It took many years of sacrifice, heartache and tragedy, but eventually, Sam got to live the normal life he'd always wanted. Although Sam lost Dean one last time, he went on to meet someone and had a son, whom he sweetly named after his brother.
Life certainly wasn't perfect for Sam, but he definitely got a beautiful and happy ending when he got the chance to be a father and live the life he wanted. Season 1 Sam was all about living a normal life and having nothing to do with the hunting world. Knowing that he got that chance, even if it took a while, would mean the world to him.
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