Part Two
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Now, I been lookin' for a job, but it's hard to find
Down here it's just winners and losers and don't
Get caught on the wrong side of that line
Well, I'm tired of comin' out on the losin' end…
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Dean is forty-three and Sam has just turned thirty-nine. In the last, increasingly frantic year, they've tried a couple dozen rituals to figure out what's wrong with Sam and none of them has worked. They go so far as summoning a seriously powerful spirit from 'across the veil', who merely says "He is as he is" and then disappears. That night, Dean finally admits he's out of ideas, and he holds Sam as he sobs, and maybe adds some tears of his own.
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Dean is forty-four and Sam is forty when they train a new hunter for the first time. His name is Brian O'Connell and he starts out careless and angry, but they temper him, travel with him, teach him, calling on the dusty memories of their father's way of creating soldiers. The Winchesters acquire a reputation as the best in the business, not just for their own hunting, but for creating hunters like themselves. After O'Connell there's Eileen Walker, Jon van den Valentine, Sondra Delaney, Zack Dauster, and, one astonishing day, Michael and Asher Roth from back in '06; a whole generation of these guys learn how to make rock-salt rounds and what the best incantation for a pissed ghost is from the Winchesters. When Michael and Asher take off, they leave a little Yoda keychain for Dean, and a note in Michael's handwriting says 'Sam- Big brothers always look out for little brothers. I'll try and keep the aging thing quiet.'
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Dean is forty-eight and Sam a few weeks shy of forty-four and they're still hunting, though for the first time Dean's doing more of the research than his brother. They've had to come to terms with the fact that Sam is going to be faster and stronger from here on out, and he'll be the one running to meet danger headfirst while Dean waits in the shadows to strike. He complains from Philadelphia to Raleigh about being the sidekick now- that is, until Sam's nearly gutted by the damn shapeshifter, and Dean's driving eighty miles an hour down I-95 in terrified search of a hospital. In the E.R. he signs all the forms with fake names, and when Sam wakes up to the name 'Hector Aframian' Dean shakily informs him he's the older one and is always going to be better at these things.
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Dean is fifty, and Sam is forty-six, but by now the years are taking their toll and Dean could pass for a good five or ten years older with his gray-flecked hair and lined face. Sam, on the other hand, looks twenty-three as ever, and they've stopped correcting waitresses who take them for father and son. They still, however, make faces when people mistake them for a couple. Sam really likes making the crack that he's 'antiquing' with Dean, to which he responds that lots of things get better with age and experience, thank you very much.
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Dean is fifty-one and Sam is forty-seven when a wraith kills Bobby. At the morgue, his sister has called ahead to say that she wants her brother buried; Sam walks in with a suit on, calls himself Andy Singer, and says his father wanted a cremation. Bobby gets a hunter's funeral before his sister even makes it to town, by which point the Winchesters are halfway across the country killing a werewolf in their friend's memory.