Every morning Ragged Dick, as he is known on the streets of Manhattan, arises from a doorway or empty crate in which he has
spent the night and begins his long day as a
bootblack. Dirty and unkempt, he is still a handsome boy of fourteen who is honest and generous; though poor, he is always ready to help someone poorer than he. To little Johnny Nolan, for example, a wretched bootblack with a dubious future, Dick offers a hardy breakfast when he sees the young boy hungrily peering through a restaurant window early in the morning.
One of Dick’s customers, a rich merchant named Whitney, admires the bootblack’s honesty and is convinced that Dick could be trusted to escort Whitney’s young nephew, Frank, a country boy, on a tour of New York City. Giving Dick new clothes and advice, Whitney watches as the two begin their excursion. The boys walk to Chatham
Street, up Broadway to Madison Square and into Central Park, while Dick, wise to the wiles of city life, thwarts confidence men and pickpockets, to the wide-eyed astonishment of Frank.
The first part of the novel concludes with Dick’s bringing Frank safely back to his uncle. The grateful Whitney gives Dick a five dollar bill, hoping it will serve as a beginning in Dick’s rise to prosperity.
More important than the five dollars, however, is Whitney’s advice and the incentive he gives Dick’s natural ambition. With the money, Dick soon opens a bank account; for the first time in his life he feels himself "a capitalist." He is more determined now to succeed and realizes that he must get an education. In a Chatham Street cafe, he meets Fosdick, another bootblack, younger than he and not as clever in the ways of New York street life. Fosdick knows how to read and write and has a sophistication that Dick respects. He hires Fosdick as his tutor and pays him with room and board. Dick has now rented a flat in Mott Street, his first step toward respectability.
Within nine months, Dick becomes literate. Through discipline and hard work he has increased his savings and even encourages Fosdick to leave the bootblack trade and become a clerk. One morning, Dick discovers his bankbook missing. The two boys suspect Jim Travis, the next-door lodger, "a bar-tender in a low groggery in Mulberry Street," and a reputed thief. They set a trap for him with the bank teller, and the next day, when Travis comes into the bank posing as Dick, he is arrested and hauled off. Now a literate young man, Dick writes his first letter to his old friend, Frank Whitney, signing it "Richard Hunter."
The climax occurs when Dick, accompanying Fosdick on a ferry ride to Brooklyn, sees a young boy fall overboard. "An expert swimmer," Dick saves the drowning boy and is rewarded by the boy’s father, James Rockwell, with new clothes and a position as clerk in Rockwell’s countinghouse. Dick’s rise is assured.