One night, Fagin leaves his apartment and the boys and travels to Sikes' small, squalid place, where Sikes lives with Nancy. Fagin has come to talk about an upcoming robbery in the village of Chertsey, outside London. Sikes' advance scout, who has been checking into the feasibility of the job, is named Toby Crackit, and Crackit has reported to Sikes that they cannot "turn" a servant in the house, in order to have an easy "in" to the house and to its valuables. Sikes says they need another plan to break into the home.
In addition to the street-crimes perpetrated by the boys, Fagin is also involved in more serious crimes, for which he needs the services of Crackit and Sikes. Crackit seems the slyer of the two—he is willing to attempt to infiltrate the house (later revealed to be the Maylies' house) with spies. Sikes, however, advocates a brute-force method for the break-in.
Sikes asks Fagin if he will pay extra for Sikes' services in breaking into the home if the break-in occurs without a man on the inside—in other words, if it's a "clean" break-in. Fagin agrees. Sikes tells Fagin that he and Crackit can break into the Chertsey house with a drill and a small boy capable of fitting through a tiny window. If Fagin can provide the boy, Sikes says, Sikes can do the burglary.
Another of the novel's coincidences. It just so happens that the house-break requires a little boy, and Fagin just so happens to have a boy he wishes to convert to a life of crime. As the novel goes on, these coincidences become more and more important, particularly as they drive the connection between Monks, the shadowy criminal, and Oliver.
Fagin volunteers that Oliver should be the boy for the job. Fagin wonders for a moment if Nancy will defend Oliver again, in front of Sikes, as she did previously, but Nancy appears amenable to the plan that Oliver should break into the house—or, at least, she doesn't betray her sympathy for Oliver's cause (it is ambiguous what her true feelings are). Fagin believes that, if Oliver successfully completes this burglary with Sikes, Oliver will see what can be gained from a life of crime, and will be "brought over" to Fagin's side. Sikes believes he can keep Oliver in line, and that Oliver is the proper size for the job.
Nancy, again showing her powerful abilities for dissembling, does not betray her desire to help Oliver. Nancy's motivations, here and elsewhere, are not always easy to understand, as she both desires to help Oliver and refuses, on the other hand, to implicate Fagin and Sikes in any way to the authorities. To do the latter, in her mind, would be to "sell out" those who have helped her attain the life she currently leads—even though it is a life that makes her miserable.
Fagin says that Oliver's innate goodness—and his appearance of goodness—would make him an unstoppable thief, since no one would ever suspect him—if Oliver could be convinced that thieving was what he ought to do. Fagin agrees to have Nancy bring Oliver to Sikes the next night. As Fagin is leaving, he remarks to himself that, although Nancy's feelings for Oliver appeared strong a few weeks ago, she has passed out of this feeling, "as all women do." Fagin resolves, when back at his apartment, to tell Oliver of his mission the next morning.
This is the fundamental paradox of Fagin's desire to corrupt Oliver: because Oliver is so serene and gentle looking, Fagin believes he will make the perfect criminal, as no one would suspect him of the ability to commit a crime. But Oliver's goodness is not, as Fagin supposes, merely superficial—it runs all the way to the core of his being, and will not be easy to eliminate.