To Frank’s surprise, Dick confronts the man, acting as though he were an agent of the police. He tells the con artist all about the sixty-dollar check and the young man who was conned. Dick suggests to the con artist that he will have him arrested if he doesn’t give the money back immediately.
The con artist hastily hands the money over to Dick and dashes from the ferry, which has just docked. Dick and Frank decide to remain on board and return to Wall Street in hopes of returning the money to the young man.
Dick will have another jolting experience on this same ferry by story’s end. That episode also comes to a pleasant end, again thanks to Dick’s morality and work ethic.
Again on dry land, they quickly find the young man and return his money to him. The young man is overwhelmed with gratitude and shakes Dick’s hand so enthusiastically that the young shoeshine boy has to ask him to stop. The boy, who is named Jonathan, invites Dick to his country home, and Dick says the fresh air would be good for his wife; with this, Dick and Frank walk away from a confused Jonathan, whom the narrator notes is likely still unsure whether or not Dick had been joking.
Dick is again coolly triumphant, and this scene reinforces his nonchalance and quick-wittedness. That the narrator notes Jonathan’s perhaps continued confusion heightens the humor of the scene.
Frank realizes that his uncle, Mr. Whitney, has probably finished up work for the day, and so decides to end his tour of the city. He asks Dick to come back to the hotel with him, however, before they part ways.
Leaving Frank behind after some eleven chapters with him feels a bit odd, but Frank’s message to Dick—and the glimpse of a better life that he showed him—remains with Dick for the rest of the story.
At the hotel, they find Mr. Whitney, who remarks that he barely recognizes Dick in his new suit. Whitney tells Dick his life story, noting that he used to be as poor as Dick was but managed to become part of the middle class through a combination of hard work and a dedication to education.
Notably, Mr. Whitney’s accounting of his early life is quite different from the one Frank gave Dick. Frank claimed his uncle was a school teacher who went into business. Whitney says he was a printer who created “an invention.”
Dick tells Mr. Whitney that he doesn’t intend to be a shoeshine boy forever. Whitney tells him that there’s nothing wrong with the shoeshine business, as it’s good, honest work. But he agrees with Dick that the boy might be able to do something more with his life. In the meantime, Mr. Whitney tells Dick to make sure that he’s living frugally and saving as much of his income as possible, only using some of it to buy books.
Whitney’s admonishment to Dick to buy books is surprisingly generic. Whitney says he attributes his success to reading, but doesn’t try to prescribe a program of reading to Dick as most people would. The mere act of reading, not the content one absorbs, seems to be the more important thing to him.
Dick agrees to this plan, and Frank accompanies him upstairs so that the boy can get his old clothes and his shoe-shining equipment. On the way, Frank admonishes Dick to stop spending his money on gambling. Dick agrees to this, too, and says he wishes that Frank were staying in New York. Frank gives Dick his address so that he can write to him, though Dick admits he’s not a very good writer.
For a while—a long while for what is, in the end, a short novel—Dick has been given a taste of another life. Returning to his bootblacking box and ratty clothes feels simply wrong. It does to Dick, too. However, if he a life like Frank’s, he knows he has to work for it.
Before Dick leaves, Mr. Whitney gives him a five-dollar bill. At first Dick doesn’t feel right about taking it, but Mr. Whitney says that he is giving him the money under the condition that, when Dick becomes prosperous himself, he will help a homeless boy in need. Dick agrees.
Charity has something of a feeling like thievery to Dick, who feels he must earn everything that he gets. When Mr. Rockwell offers Dick a lavish wage at story’s end, Dick responds in a similarly.