The novel begins by presenting its eponymous hero in his natural surroundings. Richard Hunter, who goes by the name “Ragged Dick”, is fourteen years old. He lives in New York, but since his parents are both deceased he works for a living blacking boots. During the summer months he sleeps outdoors in boxes, crates, or whatever other shelter he can find. During the winter he tries to earn enough to afford cheap lodging for the night. A physically fit and active youth, Dick is a hard worker who is basically honest. Although some of the other children lie, cheat, and steal Dick does not. He occasionally exaggerates as part of a joke, but makes sure to pay his debts. Intelligent and streetwise, Dick also possesses a strong work ethic.
Part of Dick’s experience as a low-class bootblack involve being used and preyed upon by other people higher up in the social hierarchy. For example, when Dick goes to change a two-dollar note given to him by a customer who has no small change, the note is stolen by the store clerk. Dick is unable to get it back, but when the gentleman whose note it was enters the store the thieving clerk is found out. Dick notices that the gentleman has credibility and the respect of adults, whereas Dick does not.
Dick begins the story with poor skills in terms of literacy and money management. Although he works hard and earns more than the average bootblack, he generally spends most of his earnings the same day. He enjoys cigars and does not smoke the cheap kind, he likes to watch plays at Barnum’s and the Bowery, and he frequently treats his less fortunate friends to meals. He is also illiterate, but knows how to write his own name. These habits are presented as having been the natural result of Dick’s unfortunate early life.
Dick benefits frequently from the trust of older men such as Mr. Grayson, whose trust he earns by returning the change for his twenty-five cent piece. He and the wealthy Mr. Whitney believe he has an “honest face”, which is why he is often trusted. For example, a merchant named Mr. Whitney pays him to take his nephew Frank on a tour around the city. As part of the payment for the tour, Frank and his uncle give Dick some of Frank’s cast-off clothing, which make him look much more affluent. Dick likes the look, and he notices that people treat him differently when he is dressed like a more affluent person. Accordingly, he develops a desire to improve his life and his financial position.
The tour of New York goes on for several chapters. The reader learns a great deal about the different kinds of thievery and crooked behavior that occurs there, because Dick offers the information freely to Frank along with a discussion of the different buildings along Fifth Avenue. Frank and Dick have several adventures, such as an incident in which Frank is falsely accused of having stolen a woman’s wallet. Dick succeeds in helping a victim of a crime recover his fifty-dollar bankroll, and the boys stymie a con artist. Throughout these chapters, Dick displays his sense of humor, his intelligence, and his basic honesty. Impressed, Frank and his father advise Dick to go to school.
Dick cannot afford school, but with the five dollars in his pocket from his fee for conducting Frank’s tour and a small amount of earnings from blacking boots that day, he becomes aware that continuing to live as he has done so far—sleeping out of doors, for example—will jeopardize his new suit of clothes and most likely result in him being robbed for his savings. Accordingly, he opens a savings account and rents a room for seventy-five cents per week. The room on Mott Street is cramped and untidy but serviceable. Dick also opens a bank account and deposits his five dollars. He puts the bank-book in the bureau drawer in his rented room.
Dick engages Henry Fosdick, another orphaned bootblack, as a tutor. In exchange for sharing his rented room, Dick takes lessons from Henry in reading, writing, arithmetic, and other things that Henry learned in school before his father died. The boys also attend church and Sunday school with Mr. Grayson, who is impressed by Dick’s honesty when he returns the change from his twenty-five cent piece.
A common theme in the novels of Horatio Alger Jr. is the way a boy or young man can benefit from the mentorship and guidance of an established older man. Mr. Grayson, who himself worked his way up from a poor start in life, becomes a mentor to Dick. He invites him and Henry into his Fifth Avenue home as visitors and including the boys in his Sunday school class. He routinely points out other men who have succeeded in becoming shopowners through hard work and effort. As a result of his association with Mr. Grayson, Dick becomes interested in learning the habits of the middle and upper classes. One of the first virtues Dick learns is the value of saving and investing money. Instead of spending all he earns on trips to the theater, he comes home early and reads with Henry.
Throughout the story, Dick’s past and circumstances work against his upward mobility. Mickey Maguire is a constant irritation, and an itinerant boarder steals Dick’s bankbook. The thief is caught, but the setback shows Dick that he and Henry Fosdick need to move to a better location. From time to time, Dick and Henry are mocked by boys from more affluent backgrounds. They notice that boys with parents and family connections are far more likely to get work opportunities than those without.
Throughout the story, Dick is willing to help people less fortunate than himself. He lends or gives money freely to other bootblacks whose families need the money. He also sacrifices some of his own earnings in order to buy Henry a new suit of clothes to wear while seeking employment in a shop or office. But there are so many boys applying for work that the twelve-year-old Henry is unable to compete with them. Eventually Mr. Grayson happens to come by while Henry is interviewing for a job in a hat store, and once again the influence of an older, well respected man results in a lucky break for a boy who needs it. Henry gets the job, and starts to earn three dollars per week. According to an online inflation calculator, in 1868 when Ragged Dick was published, three dollars were worth a little less than $49 in 2016 dollars. This is not a living wage, however since Henry’s expenses are low due to his sharing a room with Dick, Henry is still able to save money.
Nine months later, Dick risks his life to save a little boy who falls overboard from a ferry. An outstanding swimmer, Dick dives into the water and rescues the boy who turns out to be the son of a wealthy industrialist and financier named James Rockwell. Rockwell offers Dick a job in his business at a rate of ten dollars a week. This sum is more than enough to relieve Dick’s financial distress. He secures better lodging for himself and Henry Fosdick.
As Dick is returning to his old room to collect some of his belongings, he discovers that somebody, possibly his perpetual enemy Mickey Maguire, has stolen the clothing Dick once wore while shining shoes. Although Dick resolves to keep his boot-blacking equipment as a reminder of his early life, he does not mind the loss of the clothing.
