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Death would tell you he's never felt sympathy. Not for the women who laid dying on the streets without food or shelter. Not for the grandfather who passed with no family in sight. Not for the child on his doorstep who would never again feel the warmth of the sun, no Death did not feel sympathy.
Why should he? Watching worlds, the push and pull of the universe end time and time again,
the emotion so humanly has never gone close to him.
So he doesn't know quite what to this as he stares at the broken beated and battered soul of Sam Winchester. His body disheveled and burned to crips. He just stares as he feels what he can only assume is something akin to sympathy.
This was the first time he saw Sam Winchester die himself in that cage, but it certainly wasn't the last.
He went to grab him, take the little light that remained to heaven, out of the cage that was never meant to hold him, but just as sudden as he arrived
he vanished.
And Death stared at the empty space with a shake of his head.
_
The second time he saw Sam Winchester he had just sat down for a cherry milkshake (He, himself had never tried one before, but had always been a slight bit curious, in complete honesty)
This time his body was less mangled, his soul unfortunately as frayed as before. This time it seemed Sam could still look, his eyes darting, a deep questioning in them when they gazed upon the entity before him that Death felt he couldn't answer.
But just as before he disappeared twice as fast.
Death never finished that cherry milkshake. It looked to much like the dried blood lining every inch of the should be corpse of the man who saved the world. Death would tell you, a milkshake like that, is simply unappetizing.
_
By the thirtieth time, Death seemed to notice Sam was reconstructing himself. Learning. Grasping at the straws he was given and holding onto the to dear life. Because, this time you see, Sam Winchester could speak.
He asked Death why he didn't get him in time. Death thought no reason to lie, the archangel had no intention of keeping him dead long enough for the horseman to do anything of value. The hunter went to say something in return, but just as they both knew he would, he disappeared from view.
Death knitted his eyebrows together. For the first time in many many centuries, he was curious.
_
The thirty first time was seconds later as it was. Death asked why he had come so soon. Sam had laughed, apparently the devil overestimated how long humans could survive in negative 100 climates
Death has chuckled at this.
_
By time one hundred, Death had started slowing time. Allowing Sam a break as he called it. He wouldn't consider himself soft, or fond of the human race, simply not a hunter of his kind. But, as it was this particular human was facing the wrath of a fallen archangel, and his soul was something Death had never seen. Ripped into stripes as it fabric, craved into as if stone, beaten and shattered into shapes and pieces to small for even Death to see. But still the hunter remained.
He had asked Death what the weather on earth was like,
(in enochain of course. Death realized that Sam had long forgotten english, interesting as it was.)
Death told him, it was raining in Kansas. A particularly nasty storm. The human had told him it was fitting than.
They discussed the rain, and it's pleasantries.
_
In time two hundred and ninety five, Sam arrived completely intact, apart from the bash in his skull. Death had asked what happened, Sam had told him. He wasn't sure what he was expecting, the temper tantrum of the devil perhaps, maybe he should've expected Sam's answer when the human told him that he had banged his own head against the bars until he couldn't feel it anymore.
He told him he horseman he was tired.
They didn't talk much, but Death offered him tea. They enjoyed it in the silence.
_
In time four hundred and twelve, Sam Winchester told Death he wanted to die. He told Death he didn't want Heaven. That he didn't want Hell. Or any sort of afterlife, but instead that he simply wanted to sleep in silence until the world is ripped to shreds. Death shared this thought.
_
The next time he told Death why. Told him every small, microscopic and menial thing the devil had done. And Death recoiled in disgust.
Maybe the father of sin was too generous a title. The wrath of an archangel. It felt to Death like a toddler throwing a fit.
An all powerful being from beyond human understanding with a blood lust for everything that breathes, the apple did not fall too far from the tree. Lucifer to Death, was human.
He felt human. He acted human.
He was a sadistic abusive human madman with the abilities of an archangel, what a waste.
Death again offered Sam tea and they returned to their own thoughts with soft sips.
_
Around time seven hundred, Death began to again teach Sam Winchester english. He didn't know what it was.
Pity perhaps on the shattered soul that whispered in angel tongue, the language the one who broke him spoke. Or perhaps he just prefers human words. One never shall know will they?
Death certainly wouldn't tell you.
_
Death only walked in once. Into the cage, the bars of iron and spell. Only lifted Sam Winchester once and felt the sorrow of all the dead before him when the soul of tiny crushed up pieces and dimmed light asked him, in a silent hum,
"Can I rest now?"
And he felt true sympathy for the first time when he had to answer, "No, not yet." And lift him back into the land of the living above.