Maybe!
I haven’t had a lot of time to work on side projects this summer with how busy things are, but there’s always the chance of a few side stories with them. Of course, there is the story of Bobby first meeting Walt available if you’re interested, and I’m always welcome to people writing stories in my ‘verse!
They would be pretty shocked!
They’ve both been father figures for Sam in a life where he can’t predict where he’ll end up next, and he’s grateful to both of them. If he could bring Walt somewhere safer, he’d love for them to meet. He knows how Walt feels about hunters, which is the only reason he hasn’t brought this idea up.
However, Walt and the rest of the family are warming up to Dean, so who knows what the future holds…
All I can say is anything is possible in the future!
Walt for sure has never forgotten the only good human he met before Sam and Dean came along, and that particular case stands out in Bobby’s mind. It’s a driving force in him, and a huge reason for the way he reacted to first discovering Sam during Shadows and Reflections.
Brothers Apart 