Harold Clark is a strange, contradictory man, Ginny thinks. He loves showing off with his new tractor, annoying Larry greatly. One night over Monopoly, Jess points out that Harold is a lot sharper and more manipulative than he lets on. People think he’s just a silly old man, but Harold only pretends to be silly in order to get some privacy for himself: people ignore him because they don’t take him seriously.
Jess is a shrewd observer of character in general, and a good observer of his father’s true ways. Harold is an interesting character because he seems to have found a way to survive in the small, claustrophobic town: he just pretends to be an eccentric old man, so that people leave him alone.
Pete, who’s also playing Monopoly, announces that he’s talked to Harold recently: Harold is thinking about changing around his will. Ginny knows that Harold’s current will probably favors Loren over Jess. Jess jokes that Harold is probably going to leave his entire farm to the National Conservancy Society instead of giving it to his children. Nobody mentions the will again.
The inheritance plot concerning Larry’s family is paralleled by Harold’s plans to give away his property (as Gloucester’s story parallels Lear’s). Jess, who had seemed so interested in escaping from his family, now seems oddly invested in Harold’s will—even though he jokes about the matter, there’s a curious tension in the air, suggesting that he’s more interested than he lets on (why did he come back to Harold, after all?). Once again, it’s through the game of Monopoly that real-world greed and manipulation gets played out.
Before Jess leaves, he asks Ty about an area of land that Ty has been working for a long time. Jess notes that the land is heavily farmed, and suggests that if he controlled it, he would experiment with different crops and a more ambitious farming schedule. Ty is offended, Ginny can tell. The next day, Ty complains to Ginny that Jess is overly ambitious with his farming ideas because he’s done little actual farming himself—he’s book-smart, but inexperienced.
Jess seemingly wants to inherit some property from Harold: in spite of all his travels, he wants to become a farmer, and he’s not experienced or wealthy enough to become one on his own. This is important information, because it suggests that Jess, in spite of his affectations of adventurousness and innocence, wants the same things as everybody else: land and money.