Tom wrestles with the truth of his identity as Valet de Chambre. Now that he knows he was born enslaved, he laments the division of races, asking why “is this awful difference made between white and black?" (65) However, Tom quickly reverts back to his dishonest, snobbish ways. Roxy and Tom meet each month so that Tom can pay Roxy and gossip with her about the townspeople, and Tom quickly incurs a new gambling debt.

The story picks up where Chapter 7 left off. When Luigi and Angelo Cappello arrive at Aunt Patsy's home, Tom, whom everyone believes to be in St. Louis, has been in hiding for two days. That same morning, he'd gone to the Judge's house and put on girl's clothing. He became aware that Wilson saw him through the window.

Roxy tells Tom of the twins' arrival, as well as the fact that the townspeople have gathered to meet them at Aunt Patsy's. Being the opportunist that he is, and despite the fact that he knows that Wilson saw him in disguise, Tom once again puts on girl's clothing and goes out to rob the townspeople, even stopping at Aunt Patsy's to steal from her house while everyone is distracted by the twins playing the piano.