John Winchester and Azazel

John Winchester - the great father of Sam and Dean Winchester, who taught the boys how to hunt werwolves, vampires, evil spirits, ghosts, and other supernatural monsters. He has a very important role in the lives of his sons and in the series. One of his archnemesies being the Yellow-Eyed-Demon Azazel

The antagonism between John Winchester and Azazel lasted 23 years and ended in 2006 with the ultimate death of Azazel, killed by Dean Winchester. After the death of Mary Winchester, John Winchester, formally not a hunter at all, started to research demons and raised his sons Dean and Sam to become hunters too. He knew about angels beforehand, as angels had already tried to kill him and Mary when they were just teenagers in the past so that Sam would not be born to serve as Lucifer’s vessel during the apocalypse. Dean and Sam were sent back in time in season 4 (spoiler lol) where Azazel makes deals with women to start growing his own demon-infused human army. Through a deal with Mary while posessing her father Samuel Campbell, John Winchester, who was killed, gets revived, this deal building the basis of what happens in Season One of Supernatural. The Archangel Michael himself then wipes the memory of Mary and John Winchester at the end of the episode.

Jake: Go to hell.
Azazel: Been there, done that.

At the start of the show John Winchester then vanishes, Which starts the plot of the first two Seasons. Over the course of the first season, the Winchesters find out that John is hunting the yellow-eyed demon again that killed their mother and has found it. In a telephone call John Winchester then tells Sam and Dean that he can't act immediately because he first needs the Colt, an ancient weapon with which he can presumably kill the yellow-eyed demon named Azazel. Together, the Winchesters find the Colt, after which John Winchester gets killed by Azazel by making a deal with him to save Dean, who then dismantles the Reaper Tessa, who is supposed to take reap Deans soul after an accident that would have killed him if John Winchester didn’t act immediately.

And with all that the rivalry between Azazel seems to have ended, Sam and Dean are still hunting the demon, leading to a showdown in front of an literal Gate to Hell. With the help of the Colt Azazel opens the Gate, letting countless demons and souls escape, John Winchester being one of them. Being able to act due to being freed and being able to grasp the demon Azazel inside his vessel, John Winchester paralyzes the yellow-eyed demon long enough for Dean Winchester to deal final blow to the prince of hell, killing Azazel for good.

After a last shared goodbye, the elder Winchester then vanishes, seeming to ascend into the heavens, symbolizing the ultimate end to John Winchester’s war against the monsters and to his personal vendetta against the yellow-eyed prince of hell Azazel.

John: How stupid do you think I am?
Azazel: You really want an honest answer to that?
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