Here’s the thing about Supernatural:
Since Erik Kripke and Rob Singer left, the writers and the producers have never understood Sam and Dean, not really. Seasons 1-5 were a complete arc, and their characters underwent complete story arcs, so we look to seasons 1-5 for their true characterization.
Sam began with the Apple pie life, and Dean with the hunting life, but season 5 ended with Sam dead from hunting and Dean living the Apple pie life.
The crucial thing to understand here is that this was the natural progression of their characters because Dean was never really the hunter in the family, Sam was. Sam always was.
Because here’s the thing:
Sam wanted independence. He wanted to get out from under John’s shadow becuase he and John were too alike. They were butting heads. They never agreed. Sam didn’t care about his family, he cared about himself. He was selfish. That was his flaw, it was also John’s flaw.
Dean is the one who wanted a family. He just wanted his decimated little family to stay together and be happy together, but they never would. Dean kept trying to force a life that would never happen. That was his flaw. It was also Mary’s.
(Mary who left hunting because she wanted a family. I don’t acknowledge her resurrection character development because I believe it’s contrary to her very nature)
Becuase Sam was always a parallel for John: the one who couldn’t let the hunt go.
And Dean was always a parallel for Mary: the one who just wanted a family.
(The episodes you really see this in are 1x20 and 2x01. Dean defers completely to his father and his brother. He’s practically docile. They are the big personalities, and he is the peace keeper. All he wants is for Sam and John to get along and they simply will not.)
That’s why ending the show with Dean dead from a hunting accident, and Sam living the Apple pie life doesn’t work, because it’s contrary to their characters.
The writers in the later seasons didn’t get that. The season finale almost gives the show an “it was all a dream quality,” because it’s like Sam’s life as a hunter began and ended with Dean. Dean crashed into his life and disrupted it, only for it to get back on track 15 years later after Dean dies. Dean is almost supernatural himself in this ending - and it reduces his character from a real complex person with feelings and desires into a tool for Sam’s character development, or worse: a figment of Sam’s psyche.
One of the major aspects of Dean’s personality is that he is domestic, and that’s something that the writers have been writing around for the last 7 or so seasons. They’ve turned him into this ultra-butch hunter with no life outside the job. We’ve only gotten glimpses of the original Dean - in his interactions with Charlie who he treats like a sister, Cas who he treats like a brother, and Jack who he treats like a son.
To me the moment the writers lost their hold on Dean was when he hated Jack on sight. Dean Winchester became a parent at the tender age of 4, and since then he has always been paternal. When Dean saw Jack - a newborn, a child, a boy, an orphan - and wanted to kill him simply for being Lucifer’s son, I knew the Dean I loved was gone.
So ending the series like this was stupid, but not just because of the lose ends, the lack of half the main cast, or the unfulfilled plot lines. It was stupid because the writers didn’t understand the characters themselves, and no one was able to tell them why they were wrong.
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