Thanks to rirren and Jenjoremy for (however inadvertently) inspiring me to finish something.
"If you think about it seriously, all the questions about the soul and the immortality of the soul and paradise and hell are at bottom only a way of seeing this very simple fact: that every action of ours is passed on to others according to its value, of good or evil, it passes from father to son, from one generation to the next, in a perpetual movement."
-Antonio Gramsci
April 9, 1958*
Henry Winchester loved his jobs - both of them. After all, it was one thing to pursue a noble calling, but being a Man of Letters wasn't exactly a pro ball career, and he had a family to provide for - what with a four year old son, and he and his wife Millie trying for a second child. The small stipend traditionally provided by The Order had gotten even smaller in his father's time, and anyway, the leisured gentleman scholar would have been a little conspicuous in mid-century mid-America. So, he had gone into law, a world where it was perfectly natural to spend long hours poring over musty old books and acquiring a working knowledge of Latin.
He looked forward to his initiation for his true mission for more than the obvious reasons. Though not required by The Order, it was strongly encouraged for inducted members to reveal to their spouses the truth about who they were and what they did. Secrets of that magnitude made for unhealthy marriages, and stable families were the foundation of maintaining the legacies. Henry had obligingly married a good woman (one approved by The Order, of course), and, as she was not coincidentally not stupid, she could not believe that even a law student needed so many nights away from home for "research," and was clearly on the verge of accusing him of expending his time on something much more sordid. He needed, wanted her to know, yearned for her to be a full and equal partner in preparing for the destiny of their son. Or sons, if the Fates were kind to them.
His only regret was that his own father was not there to see him now, twenty-six years old and on the brink of becoming a fully-fledged Man of Letters. The elder Winchester's life had been cut short a decade prior by mundane disease, granting him just enough time to indoctrinate his son in the nature of the family profession. Time enough to explain that the safety of the world depended on guardians of knowledge. Yes, there were hunters, men on the ground, but theirs was a narrow world, guided by baser instincts to kill blindly, utterly lacking the understanding of a life dedicated to service. Only the Men of Letters - preceptors, scholars, academics, intellectuals, thinkers such as themselves - were positioned and prepared to understand the big picture. Only the Men of Letters could truly comprehend what it meant to dedicate one's life to a greater good, protecting people from enemies they didn't even realize they had.
Henry Winchester took comfort in knowing that his father would have been proud of him.
January 24, 1971
John Winchester was going to enlist; it never once crossed his mind not to. It didn't have anything to do with being brought up by a mother who had to struggle every day of her life because of "men who ran away from their responsibilities." He did it because when he heard Kennedy's challenge America to "Ask not what your country can do for you, but what you can do for your country," John felt as if the President had been speaking directly to him. He didn't worry about graduating from high school when there was a war on.
He sure as hell wasn't going to cower behind a blackboard and a desk like the guys he saw using college to hide from the draft – cowards who stayed behind in a soft life while others made the sacrifices to maintain that way of life.
He wasn't doing it for glory, which was a good thing, because as it turned out, there wasn't much of that on offer. What he got, instead, was mud, blood, and too close of a look at too many things that would give him nightmares for the rest of his life.
It was the right thing to do, he knew in his heart, even if it was for a country that greeted his return with an unsavory mixture of contempt, shame, and silence.
John Winchester tried not to wonder whether his own father, at least, would have been proud of him.
April 9, 2001
Sam Winchester knew what he needed to do. He had been accepted into Stanford University with a full ride scholarship, and he was going, no question. The hunting life was killing him. Not literally – though he sometimes thought that that wouldn't have been so bad – but it was killing him inside, and he had to get out, at least for while. Surely he had something else to offer to world. More than once, law had called to him.
Oh, he knew the jokes about lawyers - even hunters made them - but it wasn't as if he were going to go into corporate law and defend chemical manufacturers, or spend his days searching for loopholes to keep child molesters out of prison. He could use his skills to protect abused women, or help exploited workers, or advocate for civil rights. Heck, if he could figure out the appropriate marketing, maybe he could do something for all the people in jail for crimes they committed under the influence of demons. There had to be some other way he could make a difference, even if it wasn't the one his family had chosen for him. Even if it meant he could never return "home."
Sam Winchester had never dreamed that the day would come that his father would be so ashamed of him.
*I moved the date from canon (August 12) for three reasons.
1) in honor of my cousin I never got to meet - died in Vietnam on April 9, 1968
2) for symmetry with Sam's departure, which could have occurred in spring
3) who the hell (besides holy tax accountants) wears a trenchcoat in the early evening in Illinois in August?