Judge Driscoll is eager to be associated with Angelo and Luigi Cappello. He takes the twins on a tour of the town and to a meeting of the Freethinkers Society, of which Judge Driscoll and Pudd'nhead Wilson are leaders. Luigi and Angelo like Wilson, and Wilson invites the twins to visit his home. This unlikely friendship, between the glamorous twins and the town fool, will prove critical to how Wilson solves Judge Driscoll's murder.

Twain foreshadows the coming trouble, and Wilson's role in solving it, by having Wilson, who lives next door to Judge Driscoll, see a young woman in Tom Driscoll's bedroom. Puzzled, Wilson visits the Judge later in the day, but neither the Judge nor his sister Rachel mention having a female visitor, and Wilson doesn't ask. What they do tell Wilson, however, is that Tom Driscoll is on his way home from St. Louis. Wilson is suspicious, and with Tom coming home, the scene is being set for the murder to come.

A flashback informs the reader about Roxy's life since leaving Dawson's Landing eight years prior, when she received her freedom. Rheumetism has cut short hher work as a steamboat chambermaid. When she goes to the bank to withdraw her life's savings, she discovers that the bank, and her money, have vanished.