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Why did Gandalf choose Bilbo Baggins to acompany Thorin?

Bilbo was not an ordinary hobbit. His mother was Belladona Took, and they say that Tooks look 'fairy' as if they had elven blood in them. This is not true, but before Tooks (Tooks are mostly Fallohides) came to dwell in Shire they were friendly with the elves.
    "Fallohides were fairer in the skin and also of hair, and they were taller and slimmer than the others; they were lovers of trees and woodlands."


    "The Fallohides, the least numerous, were a northenly branch. They were more friendly with Elves than the other Hobbits were, and more skill in language and song than in handicrafts; and of old they preferred hunting to tilling. They crossed the mountains north of Rivendell and came down the River Hoarwell. In Eriador they soon mingled with the other kinds that had preceded them, but being somewhat bolder and more adventurous, they were often found as leaders or chieftains among clans of Harfoots or Stoors. Even in Bilbo's time the strong Fallohidish strain could still be noted among the greater families, such as the Tooks and the Masters of Buckland."
    The Fellowship of the Ring, Prologue
So you see, Bilbo was not an 'ordinary' hobbit, not as much as he liked to think. Gandalf 'felt' that he was bolder than the other hobbits and he decided to have Bilbo join Thorin and his company. Gandalf (and many others) regarded Bilbo and Frodo as the best hobbits in whole Middle-earth.

Gandalf never explicitly said why he had chosen poor Bilbo to join him and the dwarves in their expedition. Being wise and proud he did not liked to explain his reasons to anyone.
    "Of course there is a mark," said Gandalf. "I put it there myself. For very good reasons. You asked me to find the fourteenth man for your expedition, and I chose Mr. Baggins. Just let any one say I chose the wrong man or the wrong house and you can stop at thirteen and have all the bad luck you like, or go back to digging coal." He scrowled so angrily at Gloin that the dwarf huddled back in his chair; and when Bilbo tried to open his mouth to ask a question, he turned and frowned at him and stuck out his bushy eyebrows, till Bilbo shut his mouth tight with a snap. "That's right," said Gandalf. "Lets have no more argument. I have chosen Mr. Baggins and that ought to be enough for all of you. If I say that he is a Burglar, a Burglar he is. or will be when the time comes. There is a lot more in him than you guess, and a deal more than he has any idea about himself. You may (possibly) all live to thank me yet. Now Bilbo, my boy, fetch a lamp, and let's have a little light at this."
    The Hobbit, An Unexpected Party
So, no one can tell for sure why he did that, but one can think, beyond the shadow of doubt that he 'sensed' that Bilbo is a 'man' for the job. References:
  • The Fellowship of the Ring, (Prologue, "Concerning Hobbits");
  • The Hobbit, An Unexpected Party.

Comment by: Augustus Bartran

You have a great site, the best I have seen, regarding The Late Great Tolkien, and wish to make a commentary, if you'll have it, on your essay concerning Gandalf's choice of Bilbo to accompany Thorin. The current contribution is good in it's own right, but I feel it doesn't address the issue as fully as it might.

In Unfinished Tales, the chapter "The Quest Of Erebor" addresses this question. Thorin's quest for the Lonely Mountain plays but a smaller part in Gandalf's much broader reckoning. Sauron (named in The Hobbit only as The Necromancer) had taken residence in Mirkwood, and Gandalf feared that he good put Smaug to evil purposes abroad.
The Dragon Sauron might use with terrible effect. Often I [Gandalf] said to myself: 'I must find some means of dealing with Smaug...'

[Unfinished Tales, pg. 336]
Thus he aided and encouraged Thorin's quest. But he knew the dwarves alone would fall in this feat. Gandalf had taken interest in a place known as "The Shire", in it's "pipe-weed", but also the folk that dwelled there. In the same chapter, he discusses his interest in Bilbo.
Somehow, I had been attracted to Bilbo before, as a child, and a young hobbit... He had stayed in my mind ever since with his eagerness and his bright eyes, and his love of tales, and his question about the wide world outside of the Shire.

[Unfinished Tales, pg. 337]
Gandalf of course knew of the nimbleness and ability of hobbits to move without sound of footfall, and vanish from sight quickly (their skill at this was to be matched only by Elves, and Gandalf would be hard pressed to find and Elf that would bear a band of dwarves, or vice versa) as Gandalf also states in "The Quest of Erebor".
Suddenly in my mind these three things came together: the great Dragon with his lust, and his keen hearing and scent; the sturdy heavy-booted Dwarves with their old burning grudge; and the quick, soft-footed hobbit, sick at heart (I guessed) for a sight of the wide world.

[Unfinished Tales, pg. 337]
Gandalf understood the mission's need for stealth that dwarves simply didn't possess, for they tramped along with no heed of the clammor they made. Even Yavanna, wife of the Dwarve's creator Aule, foretold that they would have no care in such things (I wish I could bring forth a quote, but my copy of the Silm is MIA). Indeed, we see the hobbit's abilities shine again and again in The Hobbit: The Troll encounter, escape from Gollum's lair, his lurking in the wood elve's hall, and finally, the first confrontations with Smaug. Aside from all this, perhaps Gandalf had a subconcious premonition of the role he would play in the discovery of the One Ring. Either way, old Bilbo filled the role as well as anyone could.

Me again, and upon reading further, I uncovered more reasons I didn't mention in my comment. I would be most appreciative if you would take the following as part of my other comment on Bilbo and the Dwarves...

Gandalf, it seems, was looking for a hobbit before he thought of Bilbo. He came to The Shire looking for a companion for Thorin & Co, and began asking around for such a hobbit. He soon found what he was looking for: a hobbit yearning for adventure (quite a rare thing). He hears of Bilbo, and his strange doings, and is intrigued.
As soon as I entered the Shire, I heard news of him [Bilbo]. He was getting talked about, it seems. Both his parents had died early for Shire-folk, at about eighty; and he had never married. He was already getting a bit queer, they had said, and went off for days by himself. He could be seen talking to strangers, even Dwarves.

Unfinished Tales, pg. 337
Not only Dwarves, it seems, but Elves as well, as he found out when he asked Holman the gardener for him.
Off again. Why, I'm afraid he'll go right off one of these days if he isn't careful. Why, I asked him where he was going, and when he would be back, and 'I don't know,' he says; and then he looks at me queerly. 'It depends on if I meet any, Holman,' he says. 'It's the Elves New Year tommorrow!'

[Unfinished Tales, pg. 337]
So Gandalf had completed the Company for Erebor, in his mind anyway, though Thorin was yet to be persuaded.

He had found his hobbit with wanderlust, and completed the Company of Erebor.
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