Supernatural's Sam Winchester may be too precious for this world, but there were several times he also gutted us to the core with his awful decisions and actions. Sammy doesn't want to be a hunter in the first place, even though he's quite good at it, but he's such a sensitive and kind soul (when he has one) that he makes the best of it and tries to save lives every day.
That's why it stings so badly whenever Sam deviates from his usual self and breaks all of our hearts. We kind of expect Dean to be a jerk every now and then, but when his baby brother is callous or malicious it feels like a mortal blow.
He Offed His Werewolf Lover
What kind of man offs a woman after he's gone to bed with her? That's just what Sam Winchester did in the 17th episode of season two after falling for Madison. Since she only became a werewolf when asleep, it seems as if the brothers could have done something to help her. Maybe there was even a spell that could have been used. They've made exceptions for other monsters over the years but not the one Sam just slept with.
When Madison realized what she'd become, she asked Sammy to off her and although he cried, he agreed to do it. At least we didn't have to see it done. That would have been too harrowing.
He Offed Dean's Daughter
What kind of world are we living in when Sam Winchester is willing to off his own niece? When Dean accidentally fathered a child with an Amazon warrior (way to be responsible there, Dean), she quickly grew up and was sent to slay him, as Amazons apparently do in Supernatural.
Dean hesitated to take out Emma, his daughter, so Sam did it for him, and that was that. It was terrible, it was never mentioned again and it's one of the darkest moments of the show. How awesome would it have been if they'd trained her to be a hunter instead? And how could either of them discount her so quickly when family is supposed to mean everything?
He Didn't Look For Dean In Purgatory
What kind of brother was Sam when Dean was trapped in Purgatory between seasons seven and eight of Supernatural? The brothers always put family first, seeking one another out whenever they're in trouble and even going as far as to sacrifice themselves for each other. It often comes off as a little too over the top, which is why the writers probably changed this arc for Sammy, but it still made him seem so callous it hurt our hearts.
Sam's excuse is even flimsy, saying that he knew it was what Dean would have wanted for himself had Sam been sent to Purgatory instead. While Dean did move on after losing Sammy in season six, it still feels like a jerk move, especially since they made it through that season together.
He Brought About The Apocalypse
Drinking demon blood? Are you really serious, Sammy? Not only did Sammy trust Ruby and do whatever the demon said to become a better hunter when she was basically just a pretty face wrapped in red flags, but he also broke the final seal, freeing Lucifer and literally releasing Hell on Earth.
Sammy is supposed to be the smart and sensitive one, so it broke our hearts when he didn't listen to his brother, or what should have been better instincts, when it came to following Ruby's terrible advice. So much pain can be avoided when the brothers just listen to one another and this was one of several instances where Sam was not the voice of reason.
He Had Really Rotten Luck
Sometimes when Sam breaks our hearts, it's because we're crying with him and not over the things he's done. In season three's "Bad Day At Black Rock," Sam loses a lucky rabbit's foot to Bela Talbot and everything bad starts happening to him, including a moment when he pathetically and ridiculously loses a shoe down a drain.
Sam's life is in mortal peril after losing the cursed object, but it's one of those episodes that makes us both weep and laugh for poor wee Sammy. The expression on his face alone is that of a kid who just had his bike stolen.
He Dated Ruby
To this day, we can't understand how Sam Winchester trusted and slept with Ruby, the demon who was only using him to free the devil himself. Sam knows better than this. Sam has exercised caution with so many lesser evils only to fall into bed with a demon--and not even a more benign demon like Meg, who's actually helped him out on occasion!
All jokes about it being meant to be because Jared Padalecki and Genevieve Cortese became one of the cutest celebrity couples ever won't excuse the fact that Sammy was completely wrong in this decision and it was just painful to watch unfold.
He Left Adam In The Pit
This one's on both Sam and Dean, and given how the brothers say to always put family first, it's even more rotten of them to leave their little brother, Adam, whom they'd never even known about, in the pit to be tortured for eternity.
It's one of many plot arcs that viewers hope will be resolved by the end of the final season, especially since it's barely even mentioned and the brothers have always sacrificed everything for one another to help each other escape similar fates. Sam and Dean haven't done justice for many of the victims caught in their crossfire but this is one of the worst examples.
He Sacrificed His Happiness
Our hearts ache when we recall every sacrifice Sam has made along the journey so far. From losing both his future and his fiance in the first episode to throwing himself in the pit to save Dean, he has literally given everything he has to try and save other peoples' lives. The time he tried to give his own soul for Dean's when Dean went to Hell was one of the most harrowing. He's had a chance at a normal life several times but he's never been able to stick with it, in the end choosing his duty over his own happiness.
Sam is far from perfect, and we've wept over the many times he's proven this, but he's also one of the best heroes of modern TV because he never quits for good.
The Angst He's Dealt With
Watching Sam undergo so much physical pain and mental stress over the years has made many a fan anxious as a result. Sam has dealt with more trauma than any human ever should, from being literally tortured and possessed to having the devil himself inside his mind. One of Sam's bleakest moments showed him recovering from Lucifer's possession in the hospital and it was hard to handle this broken Sam.
The same occurred when Sam attempted to finish the trials, confessing that he knew he'd lose his life in the process but that he deserved to do so because he couldn't be trusted.
He Had No Soul
Soulless Sam was one of the hardest experiences any Supernatural fan had to endure. On one hand, it was kind of fun to explore what Sammy might be like without his trademark conscience, but overall it was just too dark to bear. He let his brother get turned into a vampire, he tortured people for information and he even tried to take out Bobby Singer when Bobby wanted to return his soul!
You do not mess with Bobby Singer. Not even Sam Winchester gets a pass for this one, and it had to be hard for Bobby to deal with the idea of his surrogate son wanting to end him long after they'd returned Sam's soul.