Frank asks Dick about his early childhood. He learns that the boy has always lived in New York and has been on the streets since he was seven years old. Both of his parents died when he was very young, and the woman with whom they left him died shortly thereafter. That woman’s husband deserted Dick, leaving him to scrounge a living on his own.
Dick made his living in a variety of ways before becoming a boot-black. He was a newsboy, until he tried to sell more papers by falsely announcing the death of Queen Victoria—something for which he later felt quite terrible. For a while, he also tried to sell matches, but found the business unprofitable. Throughout it all, he tells Frank, he never stole, although it would often have been easy and profitable for him to do so.
The number of times that Dick says he doesn’t steal—or the narrator informs the audience that Dick doesn’t steal—is impressive. Certainly, it speaks to Dick’s sense of doing the right thing. But it also seems to speak to a societal prejudice against the homeless: namely, the belief that because one is homeless, one must be a criminal.
Dick thanks his companion and says that he wishes more people were like Frank and Mr. Whitney. Frank again assures Dick that the shoeshine boy’s fortune might one day change, adding that Mr. Whitney himself was not always rich. He was once a poor school teacher but worked himself up through the world of business. Like Dick, however, Mr. Whitney earned his success by adhering to strict moral code.
This is the first of two stories presented to Dick regarding Mr. Whitney’s upbringing. It is the far more plausible of the two in that it relies less on luck and more on hard work. For Whitney, as with Dick, fortune favored him because of his industriousness. In the second story, this is far less true.
Frank questions Dick about his schooling and suggests that the boy attend a night school to enhance his education. Dick agrees that this would be a good idea. Frank tells his friend that a better life is possible, if Dick will attend to his education and always work hard and with integrity.
When Dick later meets the highly educated Fosdick, it becomes clear why education alone isn’t enough to ensure success in the world. Without Dick’s drive to work, the education will be useless.