Grandfather was first and foremost a pioneer in his day West or like he says, "Westering". He had led a life of great events and major adventures. He was a person who looked ahead and forward back in his better days. Unfortunately , times changed and, according to Grandpa, people are not "Westering" anymore.
Grandfather is old now, and in the story he tells over and over those tales from the past, and annoying everyone in his family.
However, the importance that Jody gives his grandfather and the weight he puts on the grandfather's experiences is what automatically places grandfather as a "leader of the people"; a person who led a group into a new and unknown way of life without fear, and he motivated his fellow comrades to do the same. Along the way, he did things no other person would have dared to do. The feelings of leadership and adventure are shared by Jody and, given the situation in an unhappy family, it is his grandfather who makes it all make sense.