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I'll admit, Gandalf did manupilate things pretty well, but I don't think he planned everything out. I think getting Bilbo as a burglar was simply luck because, although he saw something special in the hobbit, he didn't know what exactly he would do. I think he saw that Bilbo could help the dwarves, but didn't know exactly how big a role the hobbits would play in the whole sceme of things.
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