Does anyone else find it a little sad that Dean is the only Winchester to identify the “family business” as “saving people, hunting things,” where saving people is the first priority? It wasn’t John’s priority. He was on a vendetta against the “thing” that killed Mary and anything evil that got in his way got ganked. Saving people was a happy by-product of his true aim: revenge.
After Dean gives his now-famous line, Sam counters with “…I gotta find Jessica’s killer. It’s the only thing I can think about.” For Sam, saving people didn’t come first, like John, hunting was a means to an end, in the earliest seasons.
But for Dean, a character whose entire sense of self had been sublimated into a need to save and protect others, “saving people” came first. His need to save everyone, especially in those earlier seasons, came directly from what he believed his father wanted to achieve as a hunter. He believed that John’s goals were to save people, first and foremost. And so, Dean believed if he just saved enough people, if he protected Sammy well enough, John would be proud of him. And if Dean saved people, other children wouldn’t have to go through losing a parent to monsters and demons like he did. Other families wouldn’t be torn apart at the hands of evil.
But Dean could never make John proud by saving people, because that’s not what John valued. And there is no way to save everyone, so Dean could only ever fail in his goal of saving people. Dean’s tragedy is that even his laudable traits are turned against him, increasing his self-loathing through guilt and blame for his failure to meet an impossible standard. No wonder it’s such a crushing burden.