Through Simon Wheeler’s physical description, we realize that he’s old and appears not to be able to win the battle of wits but, like the old mare, Andrew Jackson, and Dan’l Webster, there’s more to him than meets the eye!
Through the diction of the narrator, we realize that he’s educated and more sophisticated than his counterpart, Simon Wheeler, whose speech indicates he’s uneducated, though clearly clever and also very aggressive in pursuit of an audience for his stories.
Simon Wheeler’s appearance combined with his location in an old, "dilapidated" tavern indicates that he probably hasn’t been economically that successful in his life. Mining towns tended to be populated by a lot of single men with too much time on their hands. One way of passing the time was to tell stories.