The way Azazel was rooting for Sam Winchester to win including shaping his life to be the king of hell while Jake Talley still ended up as the true winner. The way Jake wasn't who Azazel was betting on. The way Azazel was happy for Dean bringing Sam back because despite the obvious ways in which that puts Sam in a place beyond his skill level, making Azazel's games inherently unfair, it wasn't technically cheating. The privilege Sam held: as the wanted legacy king of hell.
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