-some spoilers for 15x20
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Dean Jr. stands over his father, Sam, as he looks up at him. He sits down next to him, listening to his labored breathing. "It's okay, Dad. You can go now." he holds Sam's hand, tearing up. He watches as his head drops to the side, the monitor starts a flat lining sound as Sam's grip on Dean Jr.'s hand releases. He's dead, the great Sam Winchester is dead.
-45 years earlier. October 31st, 2005-
Dean stands in the apartment staring at Jess and Sam. "Dad hasn't been home in a few days." he says, Sam chuckles "So he's working on a Miller-Time shift. He'll stumble back in sooner or later." Dean looks at the ground before looking back up at him, "Dad's on a hunting trip, and he hasn't been home in a few days" and with those few words, the Winchester family legacy started.