Oliver wakes the next morning to find a new pair of shoes by his bed. Fagin soon informs the lad that he is to be taken to Bill Sikes. Accustomed as he is to an unpredictable life, Oliver feels little curiosity. Before Fagin leaves in the evening, he sharply warns Oliver to obey Sikes without question because Sikes is absolutely ruthless.
Oliver reads from a book that the old man gave him. The volume contains lurid accounts of the lives of infamous criminals, filled with horrifying details. The boy is so unnerved by what he has read, he fervently prays that he be spared the fate of an evil life.
Nancy comes to take Oliver away. She is visibly upset, and Oliver senses that something injurious is in store for him. He considers briefly appealing to Nancy for aid, as he can see that he has "some power over the girl's better feelings." After a moment of hesitation, the boy decides that at the relatively early hour there will be people in the streets to whom he can turn.
Nancy, on her part, guesses what is passing through Oliver's mind. She swears that she has tried to help him, but nothing can be done at this time. For her efforts on his behalf, she has already been beaten. If he talks to anyone in the streets, both of them will suffer more harm.
Nancy takes the boy by the hand and quickly pulls him outside and into a cab. When they arrive before Sikes's house, Oliver is momentarily tempted to cry for help but refrains for Nancy's sake.
By means of words and demonstration, Sikes elaborates that he will shoot Oliver in the head if his young assistant tries to communicate with anyone while they are out together. Nancy translates the robber's threats into plain words.
Bill and Oliver sleep while Nancy sits up. Before he goes to sleep and later the next morning, Oliver looks for some sign of encouragement from the girl, but she maintains an air of detachment. Nancy calls the sleepers before daybreak and they leave the house.
It is a damp, windy morning as Sikes and Oliver set out. At first, the city is enveloped by stillness, but it gradually comes to life. Oliver is astounded by the uproar in Smithfield, where it is market day, bringing together a jostling crowd of "unwashed, unshaven, squalid, and dirty figures."
But Sikes and Oliver hasten westward through London. They receive a ride on a cart, and Oliver begins to wonder as they pass beyond a succession of suburbs. In case Oliver has any thoughts about seeking help, Sikes periodically draws attention to the pocket holding his loaded pistol.
They leave the cart and proceed on foot. After lurking in the fields around Hampton, they enter the town and have dinner in an old public house. One of the patrons transports them some distance farther in his cart. The night is very dark and cold. On foot again, Sikes leads the boy through Shepperton. At last, near a flowing stream, they come upon their objective. It is a crumbling old house, apparently deserted, which they enter.
They are first greeted by Barney, who was last seen as a waiter in the Saffron Hill dive. Within, they find a rather gaudy individual, the illustrious Toby Crackit. When food and drink are produced, Oliver is forced, over his protests, to swallow half a glass of wine. The men then compose themselves for a nap.
At half past one, all arise and Barney assists Toby and Bill in equipping themselves. With Oliver between them, they plunge out into the cold, foggy gloom. The party cross a bridge and then walk directly through Chertsey. A stone wall is scaled, and they cautiously approach a house.
Oliver suddenly understands what Sikes has plotted, and he becomes "well-nigh mad with grief and terror." He is near collapse; breaking silence, he desperately begs Sikes to liberate him. The vicious felon cocks his pistol, but Toby intervenes and quiets the hysterical boy.
When Sikes expertly removes the shutter and lattice from a narrow window in the back of the house, Oliver is instructed that he is to go through the passage and unlock the street door for the thieves. The boy is hoisted into the house and, once inside, he decides to rush up the stairs to alarm the occupants.
Sikes releases his grip on Oliver's collar; the next moment, the man is shouting loudly, "Come back!" Oliver catches sight of two figures at the top of the stairs as he is panicked by "a flash — a loud noise — a smoke — a crash." Sikes fires and drags the boy out of the house.
Pandemonium breaks loose as the two burglars retreat with the bleeding youngster. As he is swiftly carried away, Oliver loses consciousness.
The itinerary of Sikes and Oliver across the city of London through the western suburbs is detailed with lively accuracy. The description is an excellent specimen of Dickens's unrivaled representation of the great metropolis with all of its variety and teeming activity. The weather has been stormy, and the men and boy start out in the gray dawn. The night of the house-breaking is foggy and very dark. Much of the vital action of this somber novel takes place at night — and on nights that are black and rainy.
Oliver again gives conclusive evidence of his trust and naiveté. In spite of the compulsory education that he has been subjected to, he surmises that he is being sent to Sikes to perform innocent tasks. But as Oliver and Sikes approach their destination, the boy is agitated by fear that his murder is the objective of the expedition. It is not until the party have scaled the wall that he suddenly realizes that he is being dragged into some terrible crime. Belated recognition of his position strikes him in much the same manner as when Brownlow was robbed. The boy has not gained an understanding of corruption since then.
We receive ample assurance that Oliver has not been corrupted by his tempters. Fagin's collection of criminal biographies intensifies the boy's revulsion for evil ways. His resolve to risk everything to arouse the intended victims of the burglary is intended by Dickens to release the boy from any involuntary responsibility.
Nancy has been torn by a conflict regarding Oliver. Personal fear inhibits her from attempting to save the boy; although she is resigned to the lawless way of life, she has qualms about furthering the deliberate destruction of another human being. The girl wavers and catastrophe follows. A climax has been reached in Oliver's career, with his life and destiny hanging in precarious balance.