Gandalf And Bilbo
Gandalf was quite the puppetmaster throughout the 3rd Age, and unless I'm mistaken, he conscripted the dwarves to regain their territory at the Lonely Mountain in order to slay Smaug the Dragon. He wanted to remove Smaug in particular and any dragon in general from siding with Sauron in the coming war.
Why did he inject Bilbo into this adventure? It would make sense if he knew that Bilbo was going to come into pocession of the ring, but that was an unforeseen accident, wasn't it? I don't remember him being aware of Gollum this early in the story.
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