Trivia match 1

[The Might]

Well, the correct answer was given by...Team 2 only and it was indeed Bilbo.

The quote provided is indeed the one I was seeking, meaning this:
"I don't know if it has occurred to you that, even if you could steal the gold bit by bit - a matter of a hundred years or so - you could not get it very far? not much use on the mountain-side? Not much use in the forest? Bless me! Had you never thought of the catch? A fourteenth share, I supposed, or something like it, those were the terms, eh? But what about delivery? What about cartage? What about armed guards and tolls?" And Smaug laughed aloud. He had a wicked and wily heart, and he knew his guesses were not far out, though he suspected that the Lake-men were at the back of the plans, and that most of the plunder was meant to stop there in the town by the shore that in his young days had been called Esgaroth.

Well done Team 2. Team 1, I am sorry but I can not accept Gandalf as an answer as he being surprised by the taunting is not clearly mentioned and I do not think he fits as an answer.

So the score is 4-2 and we still have 3 questions to go. So here's the 3rd one:
Of what do the oldest of songs sing?

PS: Finduilas you must empty your inbox.