Because the river is too rough to travel, the group stays put for the day. While Huck and James catch fish, the Duke and the King relax openly and talk without much caution. James notices that two white men traveling with a Black man draw less suspicion than a boy and a Black man alone. The King and the Duke then discuss their next plan: in a town divided between Missouri and Illinois, they can sell James on one side and arrange his escape to the other, allowing them to profit again. The King also singles James out and warns that another escape attempt will bring even worse punishment.

Later, they walk a long distance toward town. On the way, James sees enslaved people working in the fields and is disturbed by how familiar and "normal" the sight feels. James is still limping from the Duke's recent beating, but the Duke orders James to stop because an injured enslaved man will bring a lower price. The King studies the town as a place where they might run several frauds at once, and then he and the Duke enter a tavern for drinks after threatening Huck and James to remain exactly where they are.

Outside the tavern, Huck asks James whether they should run. James answers that if they are caught, Huck will be beaten and James will be hanged, and James admits that his injured leg makes escape difficult. Huck suggests crossing to the Illinois side, but James says the legal border does not truly protect him. While they wait, Huck worries about what will happen if James is sold and cannot return. James says that would only mean belonging to another white owner, but he and Huck still discuss trying to find a quicker route back to the river.

A drunken man comes out of the tavern and talks to them. Huck tries to use the encounter to get directions to the Mississippi, but the man rambles about the river and points in nearly every direction, giving them no dependable help. Huck suggests stealing a boat if they do reach the water, but James knows that running without a solid plan could end in recapture and death. As James sits with his wounds burning, he thinks about the difference between simply running and truly escaping. Remembering how failed attempts can lead a man back to bondage again and again, James realizes he needs a real plan, and that freedom means nothing if he cannot also free his family.