A porter rouses Ragged Dick, a young bootblack who shines shoes for a living, from his sound sleep in a wooden box half-filled with straw. The porter calls Dick a vagabond because the 14-year-old boy has no home. Dick overslept after watching entertainment at the Old Bowery theatre until past midnight. The porter questions Dick about how he could pay to attend the theatre. He asks Dick if he ever steals. Dick explains: “Lots of boys does it, but I wouldn’t” (39). Despite being poor, Dick believes it is too mean to stoop to theft.

Unwashed and wearing ragged clothes, Dick is still a good-looking youth. Although some other shoeshine boys seem deceitful, Dick has “a frank, straight-forward manner that made him a favorite” (40). When a gentleman stops to have his boots shined, Dick jokes with him. Dick comically says that his overlong coat once belonged to George Washington, his torn pants came from Napoleon, and all his money is invested in the Erie Railroad. The gentleman, Mr. Greyson, tests Dick by giving him twenty-five cents for a ten cents’ shine and asking for change. Not knowing Mr. Greyson’s intention, Dick offers to get the money changed, but the man tells the bootblack he is in a hurry.