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Summary
Dean Winchester died in 2002, three months after Sam left for college.
Sam moved on with his life, assuming that his father stuck to his guns and cut Sam out for good, eventually accepting that Dean did that same despite promising to stay in touch. In 2019, Sam is 35, a partner in a successful law firm, and happily married to his college sweetheart, Jess, but his world turns on its axis when his father calls him with an address, an order, and a goodbye.
For the final time in his life, Sam goes against his instincts and follows one last order, making the long drive to Washington to finally confront his family. He finds his twenty-two year old brother sitting in a motel room with grave dirt under his fingernails and their father's dead body lying on the ground.