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Sam and Jess had gone to the bunker to understand better and to get more detail on what had happened between when Dean had tried to bring Sam back into the Life at Stanford and when Dean had shown up with a fake name needing a lawyer.
It had taken a while, but Sam had eventually come to terms with the fact that his brother was a demon and married to an angel with two kids, one of which was God himself.
Sam had grown very close to his brother, gaining back a similar dynamic to before Stanford. Which is why Dean was able to convince Sam to do the research for all of his cases again. After that, it didn’t take long before Sam started using the Men of Letters bunker to do the research for any hunter who might not have the right resources. Eventually moving to a part time job and becoming a new Bobby.
Jess eventually became known in the hunting community as one of the best nurses to go to if they needed medical attention without having to deal with the questions. She had people who could forge paperwork and fake circumstances perfectly.
Sam started only taking cases where hunters were involved, which significantly reduced his workload since most weren’t dumb enough to get caught. He also became well known as “the hunters’ lawyer”.
Years later, when Sam and Jess had a daughter of their own, Deanna, they had already all but moved into the Bunker. They had a house in Lebanon, but that turned out to be more of a façade they used for mail or when any of their friends came to visit.
Jack and Deanna grew up beside each other, becoming best friends and going to the same schools. They were joined at the hip, never one without the other.
When they got to high school they were allowed to start following Dean and Cas, or sometimes Claire, on simple salt and burns.
Eventually they started going on their own hunts together, without their family, even though they all still lived in the bunker.
Jack and Deanna became the new Winchester duo, but cousins this time. They became some of the most feared and respected hunters in the world, while staying far off the police’s radar.
Jack never used his powers as God during hunts, he still tried to be hands off on a cosmic scale. He did, however, use the power he had as a Nephilim, but only ever to heal any injuries caused by the hunt.
It didn't take long before every Hunter in the country knew, if they were ever stuck on a hunt, the Winchesters would be able to help. They were a family of monsters but they used their abilities for good. Besides, it’s not like anyone would be able to stop them even if they tried.