A wealthy businessman who mentors Dick and Henry, offering guidance and opportunities, including inviting Dick to his Sunday school class and assisting in job testimonials.

Dick's foil, another fourteen-year-old bootblack who lacks ambition and energy, earning less than Dick and often in need of direction and support.

Frank's uncle and a successful businessman who mentors Dick, encouraging him to strive for success and self-improvement with practical advice and support.

A compassionate and resourceful fourteen-year-old who becomes Dick's first true friend, offering him clothes and advice to better his life.

A stout and bold antagonist who bullies weaker boys and harbors resentment toward those who improve themselves or appear superior.

A younger, studious boy with a disciplined nature who becomes Dick's tutor and friend, helping Dick advance in his studies and social status.

The nine-year-old daughter of Mr. Greyson, representing the respectable young females in society and introducing Dick to this new social circle.

An arrogant character used to highlight Henry Fosdick's humility, who looks down on manual labor and those not of gentlemanly birth.

A young bootblack experiencing unfortunate circumstances, whom Dick helps financially due to his generous nature.

A sallow-complexioned young man who represents the novel's primary villain, embodying the flaws and bad habits aspiring boys should avoid.

A wealthy merchant whose actions reward Dick for his virtues and courageous deeds, often providing assistance in unexpected ways.