Bilbo's Pocket-Picking Attempt

Bilbo Baggins's first deliberate act of burglary—an attempt to pick the pocket of the troll William—is a comically disastrous failure that nonetheless marks a crucial step in his transformation from a comfort-loving hobbit into a resourceful adventurer. The episode, which occurs during the company's early journey east, exposes the gap between Bilbo's theoretical knowledge of burglary and his practical inexperience, while also demonstrating the unexpected consequences of his actions and the way his Tookish side begins to assert itself under pressure.

Context and Motivation

The attempt takes place shortly after the company, soaked and hungry, spots a fire in the woods and sends Bilbo ahead to investigate. He discovers three trolls—William, Bert, and Tom—roasting mutton and drinking ale. Bilbo, who has read about burglary in tales, knows that a "first-class and legendary burglar" would pick the trolls' pockets, pinch the mutton, purloin the beer, and escape unnoticed. Despite his alarm and disgust, he cannot bring himself to return to Thorin and Company empty-handed, so he decides to try the least difficult of these options: picking William's pocket.

The Attempt and Its Immediate Consequences

Bilbo creeps behind a tree just behind William, and when Bert and Tom go off to the barrel and William takes another drink, Bilbo plucks up courage and puts his little hand into William's enormous pocket. He finds a purse as big as a bag to him and lifts it carefully out, thinking, "Ha! this is a beginning!" But trolls' purses are enchanted to squeak when stolen, and this one is no exception. As soon as it leaves the pocket, it squeaks, "'Ere, 'oo are you?" William turns around and grabs Bilbo by the neck before he can duck behind the tree. The hobbit is caught, and the trolls, puzzled by the strange creature, begin to debate whether to cook him, skin him, or make a pie of him. Bilbo, terrified, tries to talk his way out, claiming he is a good cook and offering to cook for them, but the situation quickly escalates into a quarrel among the trolls themselves.

The Fight Among the Trolls

Bilbo's capture triggers a violent argument between William and Bert, who disagree about what to do with him. Bert calls William a "fat fool," and William retaliates by calling Bert a "lout." They begin to fight, rolling nearly into the fire, kicking and thumping, while Tom whacks at them both with a branch. This brawl gives Bilbo a brief opportunity to escape, but he is too dazed and bruised to take it. The fight also draws the attention of the dwarves, who have been waiting for Bilbo to return. Balin arrives first and is promptly sacked by the trolls, and one by one the other dwarves are captured until only Thorin and Gandalf remain free. The trolls' argument, prolonged by Gandalf's ventriloquism, continues until dawn turns them to stone, but Bilbo's pocket-picking attempt has already set in motion a chain of events that nearly ends the quest before it has properly begun.

Significance and Thematic Resonance

This episode is Bilbo's first test as a burglar, and he fails it spectacularly. Yet the failure is instructive: it teaches him that theoretical knowledge of burglary is no substitute for practical skill, and that even a well-intentioned attempt can have unintended consequences. The episode also highlights the tension between Bilbo's Baggins side—which values safety, comfort, and respectability—and his Tookish side, which is drawn to adventure and risk. His decision to attempt the pocket-picking, despite his fear, is a small but significant step toward the courage he will later display in the tunnels of the Misty Mountains and in his confrontation with Smaug. Moreover, the trolls' quarrel, which ultimately leads to their petrification, foreshadows the way Bilbo's later actions—such as his theft of the cup from Smaug's hoard—will provoke conflict and chaos that he must then navigate. The pocket-picking attempt, though a failure, is thus a necessary part of Bilbo's education as a burglar and as a hero.