Tommy Tucker is a waif of the streets. He works at odd jobs, when he can; he eats what he can get, and sleeps in alleys in barrels or crates, in cellars, or, when he can afford a penny, on a cot in a cheap lodging house. His style of life has made Tommy "sharp is his speech and wise beyond his years."
After a night and a morning without food ("it is no fun to be hungry"), Tommy goes to the cottages outside of town, where he can sometimes cadge a meal. An alderman is celebrating his wedding with a large feast; Tommy tries to obtain a supper. The alderman insists he sing for his supper, though Tommy explains that he knows no songs. The alderman presents him with a slice of white bread and butter on a tray — a delicacy, since the common people eat black bread of rye or barley.
A desperate Tommy improvises a song on the spot, about a bumble-bee, a spider, and a frog. The alderman finds it acceptable — but then says that Tommy can have his bread and butter once he cuts the slice into four pieces. Tommy complains that he has no knife; the alderman does not relent. Tommy says he can no more cut the bread without any knife, than the alderman could have married without any wife. Liking the cleverness of the response, the alderman lets Tommy have a knife and the bread.
At the wife's suggestion, the alderman employs Tommy as his servant. The lord mayor of the town, "a good man," comes to observe Tommy is this new role, and thinks of adopting Tommy as his son. Before doing so, however, he wants to test the boy, to see if he is "both wise and shrewd" enough to inherit the mayor's fortune. So Tommy is given three tests.
Both the mayor and alderman have little terrier dogs that follow their masters about. The two men will walk down a street in opposite directions, and Tommy must keep the dogs from following, without holding them. Tommy ties the tails of the two dogs together with his handkerchief, so that neither dog can follow his master. Test passed.
The major asks Tommy if he can put his cart before his horse and take the mayor to ride. Tommy places the horse in its harness backward, so that the beast can effectively push the cart before it. Second test passed.
The mayor gives Tommy a cup of water, and asks him to drink it up. Tommy pauses, knowing that there is a trick involved. He takes the cup into a corner of the room, where he stands on his head and drinks the water. When asked to explain, Tommy says that if he had stood on his feet he would have drunk the water down, not up.
The mayor judges Tommy to have passed all his tests; he adopts the boy as his son. Tommy receives a fine education and becomes both a great and a good man; eventually he is the mayor of the town, as Sir Thomas Tucker.
The Tommy Tucker story is one of the twelve in the collection with a Maxfield Parrish illustration.
In this story, Baum gives a harsher picture of life than he does in most of its companion pieces. Contrast a different attitude to the social problem of poverty in "How the Beggars Came to Town."