Sam chooses Amelia. They meet in the hotel room. They make love and smile together and start building a life. Dean hasn't heard from Sam in months, then years, then decades. Sam's 54 now, happy with Amelia in a little house in northern Texas. He's reading the paper one morning while she makes him coffee and he hears it. The engine. He jumps up from his chair, running outside. There in the early morning sunlight is the Impala. But leaning against it isn't who he expected.
"Cas?" he asks, still standing in the doorway.
"Hello, Sam. I suspect you know why I'm here?"
Sam's brow furrows in that way that still makes Amelia worry, because that's the tell-tale sign of him being upset. He shakes his head, trying to think of why Cas would be driving. Dean never let anyone drive that thing. Cas walks up to the foot of the porch, looking as young as the last time he saw him. Angel thing, I guess. He looks up at Sam with a strange expression.
"I'm so sorry, Sam. I thought…I thought you knew." Cas looks down at his hands.
"Wh..What's going on, Cas? Why are you here?"
"Dean wanted you to have the Impala. Thought it was right that it stayed in the family."
The realization smacked Sam in the face. The breath whooshed out of his lungs and he stumbled back. Cas raised his eyes to meet Sam's and a single tear fell down the angel's face. A sob ripped through Sam's chest, and he heard Amelia say "Honey?" from the kitchen.
Dean was gone. He was never going to see his brother again. 20 years ago that had sounded great. Now…it broke his heart. He turned around, walking back into the living room in a state of shock. He sat down, staring at nothing. And then the tears started. And they didn't stop.