Initially a little rough around the edges, especially when dealing with monsters that aren't outright evil, Dean Winchester evolves over the course of the series into a compassionate man who always seems to know what needs to be done to save people from great harm. The only time he is different is when it comes to his brother Sam, as he has proven time and time again that he is willing to sacrifice himself and the world to keep his brother alive and safe. And while that should cause a ruckus, Dean always manages to worm his way into our hearts with his slightly dim-witted nature and fondness for cake and fast food.
But there's no denying that Dean was a top class hunter who has certainly haunted the minds of monsters and hunters long after his passing. Described by his brother as a "genius" and the best hunter Sam had ever seen, there is no question about the skills he possessed in his lifetime. One can only speculate how far he would have gone if he had been allowed to live longer. Still, the trace of his existence lingers around and the feats he achieved will matter for all eternity.
But the things Dean has achieved since then seem so much bigger that the victory over Azazel seems like a pea on a mountain. Not only does he manage to climb back up from hell, albeit not entirely without help, but over the next few years he not only defies Lucifer or converses with Death, which he himself eventually becomes for a short time, but also finally kills Eve, the mother of all monsters. Through her, Dean also manages to discover a species of monster, which he eventually christens "Jefferson Starships" in accordance with the rules of discovering new monsters. But soon the Winchesters, now accompanied by the angel Castiel, find a threat that seems to be worse than any before: the Leviathans. All-eating monsters for whom God personally created purgatory so that they could be locked away. While they pose a serious problem on Earth, the Winchesters manage to defeat the Leviathans thanks to a sacrifice by Dean. Although he kills the leader of the monsters, he ends up with him in purgatory, a kind of eternal hunting ground for all monsters that are killed.
Escaping from purgatory, Dean braves further danger from an insane angel named Metatron, who once wrote down the Word of God and now wants to become God himself. Clipping his wings, Dean and Sam have to face yet another threat at the same time, as demons and other monsters still rage on Earth. One of them finally forces Dean to seek out Cain, the first murderer. He gives Dean the Mark of Cain, which enables Dean to kill the Knights of Hell. However, as he himself dies in an attempt to kill Metatron, but is unable to let go of the mark, he is resurrected as a demon. His brother manages to humanize Dean again, but the mark persists. To get rid of it, he kills Death himself and unleashes Amara, the sister of God, who has been held captive by the Mark of Cain since the beginning. Dean prevents a war between elemental powers and soon kills Lucifer once and for all, becoming an angel (or rather possessed by one) in the process. In a final battle, however, he and his brother confront the ultimate threat: God himself. Having gone mad, God destroys every world he has ever created, but with the help of friends and family, Dean renders God harmless.
"I myself was always amazed that Dean Winchester managed to fall into even greater dangers than he had experienced before. But the fact that he found his way out again was the greatest achievement." - Magnolia
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