In the setting of the 1930s, at a time in which America had always been perceived as "a land of opportunity,"people still came to this country and lived in this country with the idea that one took a certain pride in hard work, and that one was meant to work. In fact, it was perceived as a degradation of a person to accept handouts. When President Franklin Roosevelt began programs to assist the poor during the Great Depression, there were those like the Cunninghams who refused aid because they were proud and disdained pity. Atticus describes Walter's father a "a set breed of men"; Mr. Cunningham wants to farm his land and keep his voting hand free. In the caste system of Maycomb, Alabama, their refusal of charity kept the Cunninghams on only a subsistence level, but they felt themselves above such people as the Ewells, whose shiftless father gladly takes government aid to support his drinking habit.
Therefore, when Miss Caroline offers Walter Cunningham her quarter, telling him he can pay her back the next day, she unwittingly insults him. Moreover, he knows that he cannot pay her back, so if he takes it, her act, then, is one of pity, which is repugnant to a Cunningham. Walter, like his father, accepts no pity. Scout tries to explain to Miss Caroline:
"You're shamin' him, Miss Caroline. Walter hasn't got a quarter at home to bring you, and you can't use any stovewood."
Later, when Jem later asks Walter to have lunch with them at their house, Walter gladly accepts because he knows his father has paid Mr. Finch for legal services and there is a relationship of respect between them. Jem's offer, therefore, is a gesture of kindness and fellowship, not one of pity for one who is indigent.