This is the fourth in a series of lessons drawn from characters in Supernatural. If only because we know so much less about Bobby than we do about John, Dean, and Sam, this will be the most speculative class to date. The foundation of the class lies in what we have learned about Bobby as a fountain of knowledge and an emotional rock for the boys, and is predicated on Bobby sharing with them both knowledge and wisdom, and being aware of the difference.
Let me start by exploring what we do and do not know about Bobby. Unlike the case with the Winchesters, we have no clue about how or why Bobby got started as a hunter. We can deduce from the Winchesters’ history with him, from the extent of his library, and from his breadth of competence in and understanding of the hunt that Bobby has been in the game for a long time, very possibly longer than John. Running his auto salvage yard, he lives reclusively and alone, as Daniel Elkins did, but seems more connected to and comfortable in human society than Elkins was. He has active links to multiple other hunters, and seems to be an information hub, if a less public one than the Roadhouse.