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The Special Children Showdown was a contest set up by the Prince of Hell Azazel between all of the Special Children to determine who alone would survive.

Background
At St. Mary's Convent in 1972, the Prince of Hell Azazel is able to make contact with the Fallen archangel Lucifer who states that in order for Lucifer to be released, Azazel has to free Lilith from Hell and find "a very special child." In order to fulfill Lucifer's orders, Azazel begins making a series of deals in 1973 where in exchange for doing something for the person, they gave him permission to enter their home in ten years. One such person is hunter Mary Winchester with whom Azazel makes a deal after killing her boyfriend John Winchester.

In 1983, when his deals come due, Azazel visits the homes of the people he made deals with and feeds their children demon blood, turning them into the Special Children. These children go on to develop potent psychic abilities. The parents who didn't interfere in Azazel's actions he spares while those who interrupt Azazel he burns on the celling of their child's nursery.

One of Azazel's Special Children was Mary Winchester's son Sam. Due to Mary interrupting him, Azazel burned her on the celling of her home, an event witnessed by Mary's husband John. Mary's murder drove John to become a hunter seeking revenge for Mary's murder. John would train his sons Sam and Dean as hunters as well.

After the Special Children turn twenty-three, they start to come into their powers. Azazel makes contact with Ansem Weems and Scott Carey through dreams to encourage them to use their powers for malicious intent, but both are killed before they can do much.

Battle
At some point, Azazel decides to eliminate those Special Children who are too weak to do his bidding and sets up a "contest" where the Special Children will fight to the death in Cold Oak, South Dakota. Though Azazel's real intention is to have them open the Devil's Gate so Lilith will be released from Hell, Azazel lies to each one he contacts through dreams, claiming that he wants them to be the leader of a demon army he has gathered.

Azazel begins kidnapping groups of three or four Special Children and dumps them in the ghost town of Cold Oak, South Dakota to fight each other to the death to determine a "winner." One of these kidnapped Special Children is Ava Wilson who develops the power to control demons while fighting for her life against the other Special Children. Embracing her powers, Ava uses an Acheri demon that is under her control to kill dozens of Special Children over the next five months, pretending to each group that she just got there and has no idea what is going on.

Five months after kidnapping Ava, Azazel kidnaps the last group of Special Children and transports them to Cold Oak: Jake Talley, Andrew Gallagher, Lily Baker and Sam Winchester.

Aftermath
After Sam's death, a desperate Dean Winchester makes a deal with a Crossroad Demon to resurrect him. The demon gives Dean only a year before his soul is taken to Hell, something that the desperate Dean agrees to.

At the same time, the Prince of Hell Azazel, having gotten his winner, approaches Jake Talley in a dream. Azazel is able to get Jake to open the Devil's Gate in Wyoming, claiming that Jake will become the leader of a demon army that Azazel has prepared. In Wyoming, Jake uses the Colt to open the Devil's Gate, releasing hundreds of demons, amongst them Lilith which furthers Azazel's plans. In the battle that follows, Sam kills Jake, leaving Sam as the last of the Special Children. At the same time, Dean is able to kill Azazel with the Colt with the help of the ghost of John Winchester. Due to Azazel's lies in Sam's dream, the Winchesters are left believing that Azazel's plan was to release a demon army and that it had succeeded thanks to Jake.