Warning: Spoilers from seasons 1-10 below!
1.When Sam was addicted to demon blood:
Like I said, Sam didn’t really thrive while his big bro was in hell.
With Dean gone, Sam turned to the only other person he thought he could
trust: Ruby. Turns out when you hang with demons, bad things happen to
you, and the demoness got Sam addicted to demon blood by telling him it
was the only way to stop Lillith from breaking The Seals. Sadly, Ruby
was completely playing Sam, and the addiction was incredibly rough on
him physically and emotionally. Everything culminated with Dean locking
Sam in Bobby’s panic room to let his brother go through an incredibly
horrible detox alone.
2.When Sam Saved Dean and the World By Throwing Himself Into the Pit:
Because Sam accidentally brought on the end of days by letting Lucifer
out of his cage, he felt a pretty keen sense of responsibility to fix
things. Beyond that, he and Dean were told several times that it was
fated for Sam to become Lucifer’s vessel, Dean to become Michael the
Archangel’s, and the two would have a final showdown on earth. Of
course things don’t go as planned, as the boys’ half brother, Adam allows Michael use his body as a vessel instead. Sam
ultimately agrees to be Lucifer’s vessel, and while Lucifer takes
control of Sam for a while, beating the snot out of Dean, Sam ultimately
is able to overtake Lucifer, stop the fallen angel from hurting Dean,
and throw himself/Lucifer and Adam/Michael into hell, damning himself to
an eternity of being tortured by both Michael and Lucifer.
3.When Sam Confessed As He Tried To Finish The Trials:
After Sam spent most of the season
completing a series of trials that would allow the gates of hell to
close forever, Dean stops Sam as he works to complete the final
trial–curing a demon. Dean tells Sam that finishing The Trials will kill
him, and closing the gates of hell isn’t worth Sam’s death. Of course,
Sam doesn’t really care if he’s going to die, and goes on to confess
to Dean that his biggest regret and biggest sin is letting Dean down so
profoundly that Dean couldn’t trust him anymore. Sure, Sam messed up
with the whole Ruby and “starting the apocalypse” thing, but
his circumstances are extraordinary. He’s had to make crazy calls in
unimaginable situations, and even though he’s messed up, Sam has done a
lot of good. It was incredibly heartbreaking (for us and for Dean) to
watch him think that dying was the only way to really make things right.
Of course these aren’t the only times Sam’s
circumstances broke our hearts. There was that time we got a vision of
the future and Sam/Lucifer killed Dean, the time Sam had to kill the
first girl he had feelings for after Jess because she was a werewolf,
that time Sam watched Dean die over and over in the Mystery Spot, or
when he watched hell hounds drag Dean to hell. Sam has been through a
lot, but he always makes it through somehow.
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