Nothing trumps Death. He's older than even God, than even this tiny insignificant universe. One in billions. Death is the ultimate power in this universe. He skims over the land, plucking souls up here and there, taking them with a single touch of his cold hands. Nothing trumps Death, and yet the Winchesters manage to throw so many spanners into his works.
Not only have they cheated him, they've died so many times it shouldn't be allowed and they've slipped from his fingers so many times he doesn't even bother getting annoyed anymore. It takes a lot to impress Death, but these boys have managed to worm out an inkling of… not respect but something along those lines. Thousands upon thousands of years of uninterrupted work, of power, and all it took was two humans for his flow to be interrupted.
Death has a system. A system that works smoothly and effectively but these two have an amazing ability to just mess everything up, even Death. Sometimes Death slightly likes to watch the two humans. To hover around them and wait for someone to die. Because someone always does. But when they don't Death just likes to watch the boys… live. Not because he likes them, they cause too much trouble for that and Death has no bias towards anyone, he's not allowed to. But he has an odd curiosity towards them.
He can see their souls. Humming inside of them, glowing so brightly but with so many chips and scratches and scars on them. He doesn't completely understand, how such a tormented soul can still be so alive. He's seen souls that have gone through a lot less and have lost so much of their light that they already look dead. But even with all their depression and paranoia and alcoholism they shine annoyingly brightly.
Death doesn't hate them but he doesn't like them. They're interesting, that's it. He has no preference or bias towards them he is certain of it. But in saying that he won't let any other reaper to take their souls.
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