Dean's first death in is followed by dozens more as he's killed by the Trickster's time loop. During season 3, episode 11, "Mystery Spot," Dean is shot in the chest, hit by a car, crushed by a falling desk, shot with an arrow, mauled by a dog, and electrocuted when plugging in a razor.
Dean's "final" death in the episode foreshadows events later in season 3. After Dean is shot in the parking lot by a mugger, Sam spends six months looking for the Trickster, willing to do anything to resurrect his brother. He's eventually successful, although the Trickster leaves him with a lecture about how he should let Dean go, saying the brothers' constant sacrifices for each other will lead to nothing but pain.
The Trickster is later revealed to be the archangel Gabriel, who seems to be trying to prevent Sam from making mistakes that lead to the apocalypse. As it turns out, he's right to be concerned. When , Sam falls into the same dark pattern he did in the time loop, willing to go to any lengths to rescue Dean. In the four months that Dean is dead, Sam starts drinking demon blood and begins relying on the demon Ruby.
Dean's first "permanent" death is in season 3, episode 16, "No Rest for the Wicked," when he is torn apart by hellhounds that then drag him to Hell.
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