It is no secret at the start of the first Hobbit movieAn Unexpected Journey, that Thorin is dubious by Gandalf’s choice of burglar. In fact, much of the first film centers around Bilbo trying to prove himself to the dwarves, which he does in many spectacular ways. Gandalf knew right from the very start that Bilbo had a loyal heart, a lust for adventure, and more skill and bravery than anyone could have guessed, but Bilbo not only has to prove this to Thorin, he also has to prove it to himself. He has gotten used to his quaint and idyllic existence, but in doing so he has lost the spirit and the heart that makes him such a wonderful character, and he certainly has to go through lots of exciting and dangerous times to find it.
One such example is right at the start of the quest, whenthe company of Thorinis making their way through the lands surrounding The Shire, in the direction of Rivendell. Here, they encounter 3 large trolls who have come down from the mountains and started causing trouble. This trouble, of course, famously includes stealing some of the dwarves' horses and involves Bilbo being sent to steal them back. He is the company’s burglar after all! This is a little bit of a trial by fire for the poor hobbit, who, thus far, has never actually stolen anything in his life, but doesn’t want to admit that in front of such esteemed andwell-respected dwarves, especially ones who already doubt his capabilities.
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So, rather than making the sensible choice and admitting that he doesn’t know what he is doing, Bilbo decides to take this opportunity to demonstrate his courage and show them what he is made of. Although thiswasn’t included in the movies, in the book version, it’s not the horses that he is trying to steal back, but any general token of proof that he got in and out undetected. As he approaches the trio of gruesome trolls, he thinks to himself: ‘A good burglar would at this point have picked the trolls' pockets - it is nearly always worthwhile, if you’re able to manage it- pinched the very mutton off the spits, purloined the beer and walked off without their noticing him. Others more practical but with less professional pride would perhaps have stuck a dagger into each of them before they observed it. Then the night could have been spent cheerfully.’
But this voice of reason is very quickly outmatched by his Tookish side: ‘Somehow he could not go back to Thorin and company empty-handed. So he stood and hesitated in the shadows. Of the various burglarious proceedings he had heard of, picking the trolls' pockets seemed the least difficult, so at last he crept behind a tree just behind William. Bilbo plucked up the courage and put his little hand in Williams’s enormous pocket. There was a purse in it, as big as a bag to Bilbo.’
This is the item he settles upon, simply because it seems like the simplest thing to take, and brandish in front of the dwarves as the prize for his bravery and deft hands. However, this doesn’t exactly go according to plan, as there is onekey piece of informationthat Bilbo doesn’t know at this point: ‘Trolls purses are the mischief, and this was no exception. “Ere, ‘oo are you?” it squeaked, as it left the pocket; and William turned around at once and grabbed Bilbo by the neck, before he could duck behind the tree.’
That’s right, many trolls purses are actually able to speak. It’s unclear whether they are some sort of strange living creature, or whether they are magically enchanted objects, but either way, most of them are able to vocalize and warn their owners when they are about to be stolen, for just such an occasion as this. This is how, in the books, Bilbo gets himself (and the dwarves who then have to come to his rescue) into a lot of trouble. Bilbo should have left well enough alone, and returned to the company without disturbing the trolls. They could have simply gone around, and avoided the mess altogether.
However, as Gandalf rightly points out, although Bilbo gets them into trouble in the first palace, he is also the only one quick-witted enough to keep them alive whilst Gandalf gets them out of it. This is demonstrated really well in Peter Jackson’s movie depiction of the scene, where Bilbo creates conversation to distract and redirect the trolls attention, whilst Gandalf works his way towards the sunrise. The grey wizard then cleaves a rock in two,exposing the trolls to the sunlight, who automatically turn to stone. This is the same clearing where Sam points out ‘Mister Bilbo’s trolls’ years later, as the four hobbits make their way tomeet the other charactersin Rivendell in theFellowship of the Ring.
