The escape party consists of Douglass, Henry and John Harris, Henry Bailey, and Charles Roberts. Sandy Jenkins initially intends to accompany them, but eventually decides to remain. They plan to canoe up the Chesapeake Bay on the Saturday before Easter. Douglass writes travel passes, signed by their master, for each of them.

On the morning of their planned escape, Douglass works in the fields as usual. He soon feels overcome by a sense that their plan has been betrayed. Douglass tells Sandy Jenkins of his fear, and Sandy feels the same way. During breakfast, William Hamilton and several other men arrive at the house. They seize and tie Douglass and the rest of the escape party. The men transport their prisoners to Thomas Auld’s house. On the way, Douglass and the others speak together, agreeing to destroy their written passes and admit nothing.

At Thomas Auld’s, Douglass and the others learn that someone has betrayed them. Douglass writes that they immediately knew who the betrayer was, but he does not reveal who they suspected. The men are placed in jail. Slave traders arrive to taunt them and size them up as though to sell them. At the end of the Easter holidays, all the slaves but Douglass are taken home. Douglass remains in jail because he is identified as the leader and instigator. He begins to despair. At first, Thomas Auld announces his intent to send Douglass to Alabama. Then Auld suddenly changes his mind and sends Douglass back to Baltimore with Hugh Auld.

In Baltimore, Hugh Auld apprentices Douglass to a shipbuilder named William Gardner. Douglass is to learn the trade of ship caulking. Because Gardner’s shipyard is struggling to meet a deadline, however, Douglass becomes a helping hand for seventy-five different carpenters and learns no new skill. The carpenters -constantly summon and yell at Douglass, who cannot help them all at once. Tensions at the shipyard increase when the white carpenters suddenly strike to protest the free black carpenters who Gardner has hired. Gardner agrees to fire the free black carpenters. As an apprentice who is not free, Douglass continues working at Gardner’s, but he endures severe physical intimidation from the white apprentices.

One day, four white apprentices attack Douglass at the shipyard and nearly destroy his left eye. He starts to fight back but decides against it, as lynch law dictates that any black man who hits a white man may be killed. Instead, Douglass complains to Hugh Auld, who becomes surprisingly indignant on Douglass’s behalf. Auld takes Douglass with him to see a lawyer, but the lawyer informs them that no warrant may be issued without the testimony of a white man.

Douglass spends time at home recovering, and later he becomes an apprentice at Hugh Auld’s own shipyard. Douglass quickly learns caulking under Walter Price and soon earns the highest possible wage. Each week, Douglass turns over all his wages to Hugh Auld. Douglass compares Auld to a pirate who has a “right” to Douglass’s wages only because he has the power to compel Douglass to hand them over.