Young Dick Whittington, an orphan in England, has heard fantastic tales of the city of London. Three rough peddlers tell him of a street there paved with gold. They take him to London in return for pulling their cart, then abandon him in the marketplace. While Dick asks passersby where to find the street of gold, he accidentally spills the purse of Miss MacGrundy who is chaperoning her young charge, Alice. Miss MacGrundy accuses Dick of thievery and worse. She orders Hopkins, the butler, to help her punish him. Alice’s father, Mr. Fitzwarren, arrives and tells them to release Dick. Taking pity on Dick’s gullibility and recognizing his honesty, Mr. Fitzwarren offers him a job in his shipping company and instructs MacGrundy to arrange lodging for the boy in his house.
Hopkins and MacGrundy, however, have no sympathy for Dick and put him in the attic to sleep. Dick learns from Hopkins that Fitzwarren’s daughter Alice does not speak—not since the time she went to play in the attic and was found later, screaming! Dick soon finds out why. At night the attic is overrun with rats. Dick is unable to sleep, but the next morning he is still expected to begin his chores.
His first errand is to help Hopkins bring meat from the butcher shop. Hopkins, seizing the opportunity to get out of doing the chore himself, gives Dick tuppence (a coin worth two pennies) and sends him off into the city with bewildering directions. Dick becomes hopelessly lost and runs into a poor stranger and his cat. Offering Dick tea, the stranger tells him of how the tabby saved his life. The stranger offers the cat to Dick for tuppence, claiming that it will bring good luck. Dick loves the cat and gives the stranger the coin. When he asks for directions home, the stranger declares the cat’s luck will guide him.
Bells ring out that seem to announce Dick Whittington will be thrice Mayor of London. Dick feels lucky and the ringing leads him back through the streets to the Fitzwarren house. Everyone is asleep, so Dick climbs to his attic. The rats reappear, but Dick’s cat chases them away. Dick sees the cat is a true friend and gives her a special name—Trueheart.
That morning, Mr. Fitzwarren is relieved to find Dick back safe and sound. Learning that Hopkins and MacGrundy have put Dick in the attic, Mr. Fitzwarren apologizes and promises to give him a proper room. Dick introduces his cat and declares the attic rat-free. At this, the long-silent Alice speaks Trueheart’s name, which fills her father with joy and amazement. Leaving Trueheart with Alice, Dick goes with Mr. Fitzwarren to the docks to see his trading ship, the Lady Merchant, set sail.
MacGrundy pretends to care for Trueheart, but she secretly puts her into a box that is sent to be loaded onto the Lady Merchant. She lies to Alice, saying Trueheart ran away. Alice, however, suspects the truth. She goes to Dick at the docks and tells him that Trueheart is on the Lady Merchant which has just sailed. Dick is determined to follow his cat. He convinces Pinky, a seaman on another ship, the Mariner, which is following the same course as the Lady Merchant, to hire him as a ship’s mate. Alice and Dick wave goodbye to each other as the Mariner sails off.
After many weeks, Pinky and Dick dock at the distant port of Cabar. Asking if anyone has seen Trueheart, Dick is told that the ruler has a cat. Addressed as the Cabier, this ruler has two rules—no strangers admitted and no questions permitted. Since Dick is related to the Cabier’s cat and is, therefore, technically not a stranger, he resolves to speak with the Cabier—without asking any questions.
Following the rules, Dick and the Cabier engage in an elaborate guessing game about Dick’s identity and purpose. When he finally realizes that Dick has come for Trueheart, the Cabier tells Dick that for some time rats had been eating up every royal feast. Then Trueheart arrived on the Lady Merchant and vanquished the vermin. Dick cannot resist asking one vital question: where is Trueheart now? Because he is so grateful to Trueheart, the Cabier makes an exception to his no-questions rule and tells Dick that Trueheart has been kidnapped by Bloody Bess the buccaneer. The Cabier offers Dick his thanks, friendship and a bag of gold, and Dick sails off after Bloody Bess—alone. Pinky is too terrified to follow.
Finding the pirate ship and stealing aboard, Dick is amazed to see Alice swabbing the decks. She followed him over the ocean and was captured by Bloody Bess. She points out Trueheart, held captive in a cage. Dick disguises himself with the hat of a sleeping pirate, Smeary Smythe, then places a crate over Smythe to hide him. Just then Bess roars in to rouse the crew. She addresses Dick as Smythe but senses something amiss. Hearing noises from the crate holding Smythe, Bess fears the reappearance of her worst nightmare—ghost rats. The crew panics, but Dick suggests a solution—let Trueheart loose! Bess gives him the keys to the cage, but Smythe crawls from beneath his crate. Dick confesses his identity and offers to buy Trueheart back with his bag of gold. Bess takes the gold but makes Dick walk the plank. Granted some last words, Dick speaks eloquently of how it is Christmas time back in England—everyone is decorating their village tree together. The pirates are so moved by memories of home and hearth they mutiny and refuse to execute Dick. Bess escapes in the Mariner and sails off defiantly.
Dick, Alice, Trueheart and the crew sail back to Merry Old England just in time to celebrate Christmas with Mr. Fitzwarren and his company. Even Miss MacGrundy softens a little. A youngster comes up to Dick to pet Trueheart. Dick senses that this child needs some good fortune and it is time to pass Trueheart’s luck on, so he gives away his lucky cat. Everyone cheers Dick Whittington, future Lord Mayor of London!
