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Azazel met Jake in the woods threatening to kill his family if he doesn't obey his instructions. He sent him to a railroad in southern Wyoming to meet with him. Meanwhile, Dean had made a deal with the [[Crossroads Demon]] outside of Lloyd's Bar in Greenwood, Mississippi to bring Sam back, but they make the deal on the condition that his soul is claimed in one year rather than the standard ten years. They had started putting the pieces from Ash's discovery together with a little help from Ellen, who had gone to get pretzels when the Roadhouse burned to the ground. She recovered everything from a warded safe from the basement after Ash's last call to her led her there, including a map of southern Wyoming with five marks. They discovered that each of the marks represent five abandoned frontier churches built by Samuel Colt in the 1800's along with private railway lines connecting each church into the shape of a [[Pentagram]]; a 100 square mile [[Devil's Trap]] made with pure iron and an old cowboy cemetery at the epicenter. After arriving at the railway lines, Azazel gave Jake the Colt which is the key to opening a crypt in the cemetery. At first, Jake wanted to kill him, but Azazel convinced him to obey by promising that his family will be treated like royalty if he accomplishes this task and gives into his psychic powers.
At the cemetery[[Fossil Butte Cemetery]], Jake was delayed by Sam, Dean, Bobby, and Ellen. He was shocked when he saw Sam believing that he killed him after he severed his spine when he stabbed him in the back at Cold Oak and he was horrified to see him standing there. Jake was able to use his newfound psychic abilities to make Ellen turn her gun on her own head and threatening that he will make her fire if they don't drop their weapons. After they agreed, Jake used the Colt to open the mausoleum, but Sam shot Jake four times in the back. As Jake was begging Sam not to kill him, Sam shot him three more times before finally killing him, but as Dean retrieves the Colt from the lock which had shifted to the shape of a pentagram, the doors had opened unleashing hundreds of demons upon the world. It was revealed that the crypt in the cemetery was a [[Devil's Gate]]; a gateway to Hell. When the gates were opened, the Devil's trap surrounding the gate had been broken, allowing Azazel to enter the cemetery. As Bobby, Ellen, and Sam attempted to shut the gates, Dean realized that the last bullet is still in the chamber before he was attacked by Azazel. Sam came to stop Azazel from killing Dean, but he was psychically pushed onto a tree and pinned in place. Azazel started to insult Dean about him bringing Sam back from the dead and hinted that Sam came back from the dead different to mess with his head and stating that "what's dead should stay dead" as well as teasing him about the lengths he would go to for his family. Azazel was just about to use the Colt to kill Dean, but John's spirit had escaped from Hell via the Devil's Gate and wrestled against Azazel by ripping him out of his [[Meatsuit]]. John's distraction gave Dean enough time to take the Colt back and aim it at Azazel as he was returning to his vessel after throwing John off of him. Azazel stared at Dean in horror as he used the final bullet in the chamber to shoot Azazel in the heart. After one last fearful look at Dean, he started to light up orange as he was dying and his yellow eyes displayed a pair of skulls before finally fading away. After Ellen and Bobby were able to shut the gate before any more demons and spirits can exit the [[Portal]], they witnessed John's spirit who had been staring at Azazel's dead body. After having a final moment with his sons, his spirit had finally passed on to the afterlife as Azazel was finally killed, fulfilling their life long hunt for revenge for Mary's death. Despite his death, his demon army was released along with Lilith and Bobby, Ellen, Sam and Dean decided to put a stop to the over 200 demons that escaped.
Over the course of [[Season 3]] through [[Season 5]] after Azazel's demon army was unleashed upon the world, Sam and Dean had been able to discover his true plans for opening the Devil's Gate and they were able to thwart the plans to bring forth the [[Apocalypse]] with the help of [[Castiel]] and [[Crowley]] and all the other hunters working on their side.
===[[2.22 All Hell Breaks Loose: Part Two]]===
As [[Jake Talley]] is the last surviving [[Special Children|special child]], Azazel comes to him in his dreams to get him to do what he wants, though he admits that Jake isn't the child he had expected or even wanted to win. Jake threatens to kill Azazel, but he tells Jake that that is not easy to do and that others have tried. Azazel tells Jake that he has a "laundry list" of things he wants Jake to do for him, and threatens Jake's family to make Jake comply. Needing Jake to open the [[Devil's Gate in Wyoming]] to release his [[demon]] army, Azazel meets him in person at the edge of the giant [[Devil's trap (symbol)|devil's trap]] as he can't cross it. He gives Jake directions to the cemetery [[Fossil Butte Cemetery]] where the Gate is and the key to it: [[the Colt]]. When Azazel reveals that the Colt can kill him, Jake is about to shoot him with it, but Azazel only mockingly pretends to be afraid before convincing Jake to do what he wants with promises of luxury and power. Jake becomes corrupted by his powers and his eyes gleam yellow at one point, further demonstrating his connection to Azazel.
[[File:AzazelShot.jpg|thumb|left|350px|Azazel is shot in the heart with [[the Colt]].]]
