At the beginning of Supernatural, Sam was an entirely different person. Granted, over the last fifteen seasons he's seen plenty of tragedy and destruction, which would change and traumatize anyone.
Still, the dramatic changes to Sam's actions and overall personality were quite extreme. He's almost an entirely different person now compared to when audiences were first introduced to him in 2005. He's colder, he's more distant, and he's definitely made plenty of bad choices in his time, unfortunately for Dean, and in the case of the Apocalypse, the rest of the world.
10 Became Colder And More Calculating
Sam was sweet and sensitive in the early seasons; as time went on, his demeanor began to change. At first, he claimed it was to be more like Dean, as part of his preparation to live life without Dean in the picture when he went to Hell. Even after that, Sam could've chosen to maintain his former bedside manner, especially when dealing with witnesses and victims. Sometimes he could be as brutal and pushy as Dean tended to be, and audiences no longer see Sam's soft side as much.
9 His Love Life Went Downhill Fast
Sam was in a happy, loving relationship with Jessica at the beginning of the series. Upon her tragic death, however, Sam's love life took a drastic turn for the worse. A romance with Sarah later on in Season 1 appeared promising, but Sam still left her behind. Sam began falling for women that were monsters, including a werewolf and a demon, and he became more comfortable with the concept of love 'em and leave 'em. It seemed his desire for a real relationship dramatically decreased. This could be because of the devastating loss of Jessica, or even from Dean's influence given his player tendencies, but Sam could've made better choices along the way.
8 Embraced His Powers
Even against Dean's dying wish, Sam embraced his powers. He didn't listen to his brother, who had explicitly warned Sam that using his powers would lead to a downward spiral. Again, it's a prime example of Sam making a bad choice. While it could be considered a bad choice for the right reasons, given Sam wanted to save people, it still isn't worth it at the end of the day because he was listening to Ruby and playing with fire by utilizing the powers Yellow Eyes bestowed upon him.
It's dangerous, especially to Sam and those around him, and not only did he disregard Dean's wishes, but he lied about using his powers, making things that much worse. Plus, he has expressed dislike for his powers, so why did he succumb to Ruby's will and his powers so easily?
7 Became Less Honest
Sam was more open and communicative in seasons past. Sam has since become more comfortable with lying and keeping secrets, especially from his brother. Some of his greatest hits in that department include the demon blood addiction, the use of his powers, the fact that he was hearing and seeing Lucifer, and of course, getting the Mark of Cain off of Dean's arm. Sam's a hypocrite because as much as he says he hates being lied to, he still lies to his brother and several others.
6 Demon Blood Addiction
The demon blood addiction is the source of Sam's powers, making him that much more powerful and dangerous. Audiences have seen Sam recover from his demon blood addiction on more than one occasion, and the detox process is horrible to witness, especially for Dean. Sam looks more like a monster than anything when strung out on demon blood, and to this day he still struggles with it. He didn't have the self-control needed to stop himself before he got in too deep, or the will to simply say no to begin with. True, he was vulnerable after losing his brother and Ruby took advantage of that, but Dean had told him to steer clear of his powers before he died, so it wasn't like Sam didn't have a warning.
5 Lost His Innocence
In flashbacks, and in the early seasons, audiences witnessed the sweet, sensitive Sam Winchester. He was innocent, even despite having seen the monsters and nightmares he had. He let Amy go, and he still saw the good in the world, wanting to do something with his life and have nothing to do with the supernatural.
Sam's innocence is part of why audiences love him so much, and it's sad to see that part of him wither away. Sam was able to maintain a level of innocence before, so it's a wonder why Sam can't seem to do that now--though this is probably because the stuff he's dealt with in the last fifteen years was a lot worse than what he was dealing with prior to the beginning of the show.
4 Became Impulsive
Sam started the Apocalypse partially due to impulsive decision-making. Sam rushed to conclusions about his father, which was part of why he felt so guilty when John died. Sam has many a time gone behind Dean's back and made impulsive decisions. Most have led him to only more ruin and devastation. Audiences would think Sam would learn his lesson by now, but it seems Sam still has a learning curve to follow as of yet.
3 Family Became Less Important
Considering everything Dean did for Sam as he was growing up, family should mean more to Sam than his actions have shown. One of the worst things he ever did was leave Dean to rot in Purgatory while he pursued a normal life.
It's understandable that Sam wanted out of the "family business", but he still should've rescued Dean before he moved on. Plus, he and Dean left their half-brother Adam behind in the cage. Sam never seems to think about Adam much, and he didn't seem too guilty about the Purgatory thing--even though Dean would've saved Sam if the roles had been reversed.
2 Made Sacrifices Without Knowing All The Information
Sam became too rushed in his judgment. The two most noteworthy examples of this have to do with his grandfather Samuel, and his niece Emma. Sam wasn't even sure his grandfather was possessed, and still he shot him dead. Brutally so, given it was a head shot. With Emma, she may have been close to killing Dean as part of her initiation, but she hadn't done anything yet and Dean was trying to talk her down. Sam shot her without a second thought; it's amazing Dean still talked to him afterwards. Sam sacrificed two members of his family willingly; surely Dean should be concerned by this.
1 Gave Up On Himself
Sam left his family behind to attend Stanford and become a lawyer. He had grand plans, which included marrying Jessica and essentially living happily ever after. Plans don't always go accordingly, and for Sam, this is an understatement. Still, he never went back to school to pursue his dreams or become the person he wanted to be--he became like his father in many ways (a man Sam had several issues with), and lived the life he hated anyway. Why didn't he fight harder for himself and his dreams? It seems he's built up more resentment than happiness over the years by sticking around and hunting with Dean.
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